{"id":1922,"date":"2018-04-11T23:47:25","date_gmt":"2018-04-12T03:47:25","guid":{"rendered":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/chapter\/20-2-alcohols-and-ethers\/"},"modified":"2018-07-09T16:36:43","modified_gmt":"2018-07-09T20:36:43","slug":"20-2-alcohols-and-ethers","status":"publish","type":"chapter","link":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/chapter\/20-2-alcohols-and-ethers\/","title":{"raw":"10.4 Nomenclature of Alcohols and Ethers","rendered":"10.4 Nomenclature of Alcohols and Ethers"},"content":{"raw":"<div>\r\n<div class=\"bcc-box bcc-highlight\">\r\n<h3>Learning Objectives<\/h3>\r\n<div>By the end of this section, you will be able to:<\/div>\r\n<div>\r\n<ul>\r\n \t<li>Describe the structure and properties of alcohols<\/li>\r\n \t<li>Describe the structure and properties of ethers<\/li>\r\n \t<li>Name and draw structures for alcohols and ethers<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<section id=\"fs-idm30613248\"><section id=\"fs-idm10005664\">\r\n<h2>Naming Alcohols<\/h2>\r\n<p id=\"fs-idm24572576\">The name of an alcohol comes from the hydrocarbon from which it was derived. The final <em>-e<\/em> in the name of the hydrocarbon is replaced by <em>-ol<\/em>, and the carbon atom to which the hydroxyl group (OH group) is bonded is indicated by a number placed before the name.[footnote] The IUPAC adopted new nomenclature guidelines in 2013 that require this number to be placed as an \u201cinfix\u201d rather than a prefix. For example, the new name for 2-propanol would be propan-2-ol. Widespread adoption of this new nomenclature will take some time, and students are encouraged to be familiar with both the old and new naming protocols.[\/footnote]<\/p>\r\n<p id=\"fs-idp69169072\">Therefore when naming alcohols\u00a0following IUPAC, you follow the similar two rules for alkanes with modification to \"rule 1\" mentioned above.<\/p>\r\n<strong>Rule 1. Identify the longest chain of carbons which <span style=\"text-decoration: underline\">contains<\/span> the OH group and its position (PREFIX-#-AN<del>E<\/del>+OL). \u00a0<\/strong>And\u00a0when numbering the parent chain, the hydroxyl group gets the lowest possible number.\r\n\r\n<strong>Rule 2. Names and position of the substituents.<\/strong>\r\n<p id=\"fs-idp8269216\">Alcohols containing two or more hydroxyl groups can be made. Examples include 1,2-ethanediol (ethylene glycol, used in antifreeze) and 1,2,3-propanetriol (glycerine, used as a solvent for cosmetics and medicines):<span id=\"fs-idm42427552\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_polyols_img.jpg\" alt=\"Structural formulas for 1 comma 2 dash ethanediol and 1 comma 2 comma 3 dash propanetriol are shown. The first structure has a two C atom hydrocarbon chain with an O H group attached to each carbon. The O H groups are shown in red an each O atom has two sets of electron dots. Each C atom also has two H atoms bonded to it. The second structure shows a three C atom hydrocarbon chain with an O H group bonded to each carbon. The O H groups are shown in red, and each O atom has two sets of electron dots. The first C atom has two H atoms bonded to it. The second C atom has one H atom bonded to it. The third C atom has two H atoms bonded to it.\" class=\"aligncenter\" width=\"446\" height=\"210\" \/><\/span><\/p>\r\n\r\n<div class=\"example textbox shaded\" id=\"fs-idm9024448\">\r\n<h3>Example 1<\/h3>\r\n<p id=\"fs-idp1577984\">Consider the following example. How should it be named?<span id=\"fs-idm20720800\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_alcohol1_img.jpg\" alt=\"A molecular structure of a hydrocarbon chain with a length of five C atoms is shown. The first C atom (from left to right) is bonded to three H atoms. The second C atom is bonded on one H atom and an O atom which is also bonded to an H atom. The O atom has two sets of electron dots. The third C atom is bonded to two H atoms. The fourth C atom is bonded to two H atoms. The fifth C atom is bonded to three H atoms. All bonds shown are single.\" width=\"501\" height=\"154\" class=\"aligncenter\" \/><\/span><\/p>\r\n<p id=\"fs-idp3540976\"><strong>Solution<\/strong>\r\nThe carbon chain contains five carbon atoms. If the hydroxyl group was not present, we would have named this molecule pentane. To address the fact that the hydroxyl group is present, we change the ending of the name to <em>-ol<\/em>. In this case, since the \u2013OH is attached to carbon 2 in the chain, we would name this molecule 2-pentanol.<\/p>\r\n&nbsp;\r\n<p id=\"fs-idm65417856\"><em><strong>Test Yourself<\/strong><\/em>\r\nName the following molecule:<span id=\"fs-idm39569728\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_alcohol2_img.jpg\" alt=\"The structure shown has a C H subscript 3 group bonded up and to the right to a C atom. The C atom is bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded down and to the right to a C H subscript 3 group. The second C atom (from left to right) is bonded to a C H subscript 3 group and an O H group.\" width=\"272\" height=\"93\" class=\"aligncenter\" \/><\/span><\/p>\r\n<em><strong>Answer<\/strong><\/em>\r\n\r\n2-methylpentan-2-ol\r\n\r\n<\/div>\r\n<\/section><\/section><section id=\"fs-idm24652464\">\r\n<h2>Naming Ethers<\/h2>\r\n<p id=\"fs-idp6654240\"><strong>Ethers<\/strong> are compounds that contain the functional group \u2013O\u2013. Ethers do not have a designated suffix like the other types of molecules we have named so far. In the IUPAC system, the oxygen atom and the smaller carbon branch are named as an alkoxy substituent and the remainder of the molecule as the base chain, as in alkanes. As shown in the following compound, the red symbols represent the smaller alkyl group and the oxygen atom, which would be named \u201cmethoxy.\u201d The larger carbon branch would be ethane, making the molecule methoxyethane. Many ethers are referred to with common names instead of the IUPAC system names. For common names, the two branches connected to the oxygen atom are named separately and followed by \u201cether.\u201d \u00a0But if the two alkyl groups are the same, then the di prefix is used. The common name for methoxyethane shown below is ethylmethyl ether:<span id=\"fs-idm6486336\">\r\n<\/span><\/p>\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_NameEthers_img.jpg\" alt=\"A molecular structure is shown with a red C H subscript 3 group bonded up and to the right to a red O atom. The O atom is bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to a C H subscript 3 group.\" class=\"aligncenter\" width=\"299\" height=\"57\" \/>\r\n<p id=\"fs-idp69169072\">Therefore when naming ethers, the two rules are modified. \u00a0And furthermore, there are two ways that are commonly used: IUPAC method and the common method.<\/p>\r\n<strong>IUPAC method of naming ethers:<\/strong>\r\n\r\n<strong>Rule 1. Identify the longest carbon branch\u00a0(PREFIX-ANE).<\/strong>\r\n\r\n<strong>Rule 2. Names of the substituent, the other carbon branch (PREFIX+OXY)<\/strong>\r\n\r\n&nbsp;\r\n\r\n<strong>Common method of naming ethers:<\/strong>\r\n\r\n<strong>ALKYLALKYL ether \u00a0 \u00a0or \u00a0 diALKYL ether<\/strong>\r\n\r\n<\/section>&nbsp;\r\n\r\nFor example, the following ether would be commonly named ethylpropyl ether. \u00a0its name following the IUPAC rules would be ethoxypropane.\r\n\r\n<span id=\"fs-idm109423504\"><img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4b_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to an O atom. This O atom is bonded to a C H subscript 2 group which is also bonded to another C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 3 group. All bonds are in a straight line.\" class=\"aligncenter\" width=\"604\" height=\"53\" \/><\/span>\r\n\r\n<section id=\"fs-idm24652464\">\r\n<div class=\"example textbox shaded\" id=\"fs-idm48177328\">\r\n<h3>Example 2<\/h3>\r\n<p id=\"fs-idm86150048\">Provide the IUPAC and common name for the ether shown here:<span id=\"fs-idp882608\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_ethers1_img.jpg\" alt=\"A molecular structure shows a C H subscript 3 group bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to an O atom. The O atom is bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to a C H subscript 3 group.\" class=\"aligncenter\" width=\"289\" height=\"57\" \/><\/span><\/p>\r\n&nbsp;\r\n<p id=\"fs-idm451728\"><strong>Solution<\/strong>\r\nIUPAC: The molecule is made up of an ethoxy group attached to an ethane chain, so the IUPAC name would be ethoxyethane.<\/p>\r\n<p id=\"fs-idp1988576\">Common: The groups attached to the oxygen atom are both ethyl groups, so the common name would be diethyl ether.<\/p>\r\n&nbsp;\r\n<p id=\"fs-idm81417584\"><em><strong>Test Yourself<\/strong><\/em>\r\nProvide the IUPAC and common name for the ether shown:<span id=\"fs-idp6957760\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_ethers2_img.jpg\" alt=\"A molecular structure shows a C H subscript 3 group bonded up and to the right to an O atom. The O atom is bonded down and to the right to a C H group. The C H group is bonded up and to the right to a C H subscript 3 group. The C H group is also bonded down and to the right to another C H subscript 3 group.\" width=\"262\" height=\"92\" class=\"aligncenter\" \/><\/span><\/p>\r\n<em><strong>Answers<\/strong><\/em>\r\n\r\nIUPAC: 2-methoxypropane; common: isopropylmethyl ether\r\n\r\n<\/div>\r\n<div id=\"fs-idm85442272\" class=\"note chemistry link-to-learning textbox shaded\">\r\n\r\n<span id=\"fs-idm86050336\"><img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/OSC_Interactive_200-40.png\" alt=\"\u00a0\" class=\"alignleft\" width=\"113\" height=\"70\" \/>\r\n<\/span>\r\n<p id=\"fs-idp6043376\">Want more practice naming ethers? This brief <a href=\"http:\/\/openstaxcollege.org\/l\/16ethers\">video review<\/a> summarizes the nomenclature for ethers.<\/p>\r\n\r\n<\/div>\r\n<div id=\"fs-idp6839408\" class=\"note chemistry everyday-life textbox shaded\">\r\n<h3 class=\"title\">Carbohydrates and Diabetes<\/h3>\r\n<p id=\"fs-idm73541184\">Carbohydrates are large biomolecules made up of carbon, hydrogen, and oxygen. The dietary forms of carbohydrates are foods rich in these types of molecules, like pastas, bread, and candy. The name \u201ccarbohydrate\u201d comes from the formula of the molecules, which can be described by the general formula C<sub>m<\/sub>(H<sub>2<\/sub>O)<sub>n<\/sub>, which shows that they are in a sense \u201ccarbon and water\u201d or \u201chydrates of carbon.\u201d In many cases, <em>m<\/em> and <em>n<\/em> have the same value, but they can be different. The smaller carbohydrates are generally referred to as \u201csugars,\u201d the biochemical term for this group of molecules is \u201csaccharide\u201d from the Greek word for sugar (<a href=\"#CNX_Chem_20_02_Sugars\" class=\"autogenerated-content\">Figure 1<\/a>). Depending on the number of sugar units joined together, they may be classified as monosaccharides (one sugar unit), disaccharides (two sugar units), oligosaccharides (a few sugars), or polysaccharides (the polymeric version of sugars\u2014polymers were described in the feature box earlier in this chapter on recycling plastics). The scientific names of sugars can be recognized by the suffix <em>-ose<\/em> at the end of the name (for instance, fruit sugar is a monosaccharide called \u201cfructose\u201d and milk sugar is a disaccharide called lactose composed of two monosaccharides, glucose and galactose, connected together). Sugars contain some of the functional groups we have discussed: Note the alcohol groups present in the structures and how monosaccharide units are linked to form a disaccharide by formation of an ether.<\/p>\r\n\r\n<figure id=\"CNX_Chem_20_02_Sugars\">\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"1200\"]<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_sugars.jpg\" alt=\"This figure shows structural and ball-and-stick models for the common sugars fructose and lactose. Carbon atoms are illustrated in black, oxygen atoms are red, and hydrogen atoms are white in the ball-and-stick models.\" width=\"1200\" height=\"755\" \/> <strong>Figure 1.<\/strong> The illustrations show the molecular structures of fructose, a five-carbon monosaccharide, and of lactose, a disaccharide composed of two isomeric, six-carbon sugars.[\/caption]<\/figure>\r\n<p id=\"fs-idm33645104\">Organisms use carbohydrates for a variety of functions. Carbohydrates can store energy, such as the polysaccharides glycogen in animals or starch in plants. They also provide structural support, such as the polysaccharide cellulose in plants and the modified polysaccharide chitin in fungi and animals. The sugars ribose and deoxyribose are components of the backbones of RNA and DNA, respectively. Other sugars play key roles in the function of the immune system, in cell-cell recognition, and in many other biological roles.<\/p>\r\n<p id=\"fs-idm20354000\">Diabetes is a group of metabolic diseases in which a person has a high sugar concentration in their blood (<a href=\"#CNX_Chem_20_02_Diabetes\" class=\"autogenerated-content\">Figure 2<\/a>). Diabetes may be caused by insufficient insulin production by the pancreas or by the body\u2019s cells not responding properly to the insulin that is produced. In a healthy person, insulin is produced when it is needed and functions to transport glucose from the blood into the cells where it can be used for energy. The long-term complications of diabetes can include loss of eyesight, heart disease, and kidney failure.<\/p>\r\n<p id=\"fs-idm13367296\">In 2013, it was estimated that approximately 3.3% of the world\u2019s population (~380 million people) suffered from diabetes, resulting in over a million deaths annually. Prevention involves eating a healthy diet, getting plenty of exercise, and maintaining a normal body weight. Treatment involves all of these lifestyle practices and may require injections of insulin.<\/p>\r\n\r\n<figure id=\"CNX_Chem_20_02_Diabetes\">\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"800\"]<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_diabetes.jpg\" alt=\"This is a diagram of a hand with a blood droplet on an index finger and a nearby sharp pointed pen-like object. The finger is next shown touching a white and green test strip with arrows pointing to the green region where the bloody finger touches the strip. An arrow points to a small rectangular device in which the green end of the strip is inserted. An L C D display provides a reading.\" width=\"800\" height=\"600\" \/> <strong>Figure 2.<\/strong> Diabetes is a disease characterized by high concentrations of glucose in the blood. Treating diabetes involves making lifestyle changes, monitoring blood-sugar levels, and sometimes insulin injections. (credit: \u201cBlausen Medical Communications\u201d\/Wikimedia Commons)[\/caption]<\/figure>\r\n<\/div>\r\n<\/section><section id=\"fs-idm82374704\" class=\"summary\">\r\n<h2>Key Concepts and Summary<\/h2>\r\n<p id=\"fs-idm8778416\">Many organic compounds that are not hydrocarbons can be thought of as derivatives of hydrocarbons. A hydrocarbon derivative can be formed by replacing one or more hydrogen atoms of a hydrocarbon by a functional group, which contains at least one atom of an element other than carbon or hydrogen. The properties of hydrocarbon derivatives are determined largely by the functional group. The \u2013OH group is the functional group of an alcohol. The \u2013R\u2013O\u2013R\u2013 group is the functional group of an ether.<\/p>\r\nThe systematic methods of naming alcohols follow a similar procedure and the names have three main parts:\r\n\r\n<span style=\"color: #0000ff\"><strong>1)<\/strong><\/span> specifying the information about the substituents,\r\n\r\n<span style=\"background-color: #ffff00\"><strong>2)<\/strong><\/span> specifying the information about the parent chain, and\r\n\r\n<span style=\"color: #008000\"><strong>3)<\/strong><\/span> the ending which specifies what functional group is present in the structure being named.\r\n\r\n<strong>Alcohols: \u00a0 \u00a0<span style=\"color: #0000ff\">#-substituents<\/span>-<span style=\"background-color: #ffff00\">PREFIX<\/span>-<span style=\"color: #008000\">#-AN<del>E<\/del>+OL<\/span><\/strong>\r\n\r\n<strong>Ethers: \u00a0 \u00a0<span style=\"color: #0000ff\">PREFIX+OXY<\/span>-<span style=\"background-color: #ffff00\">PREFIX<\/span>-<span style=\"color: #008000\">ANE<\/span><\/strong>\r\n\r\nRemember: there are two ways that are commonly used to name ethers. \u00a0The common method is also important to know.\r\n\r\n<strong>Common method of naming ethers:<\/strong>\r\n\r\n<strong>ALKYLALKYL <span style=\"color: #008000\">ether<\/span> \u00a0 \u00a0or \u00a0 diALKYL <span style=\"color: #008000\">ether<\/span><\/strong>\r\n\r\n<\/section><section id=\"fs-idm77059568\" class=\"exercises\">\r\n<div class=\"bcc-box bcc-info\">\r\n<h3>Exercises<\/h3>\r\n1. Write condensed formulas and provide IUPAC names for the following compounds:\r\n<p id=\"fs-idm81589984\">a) ethyl alcohol (in beverages)<\/p>\r\n<p id=\"fs-idm401696\">b) methyl alcohol (used as a solvent, for example, in shellac)<\/p>\r\n<p id=\"fs-idm31515088\">c) ethylene glycol (antifreeze)<\/p>\r\n<p id=\"fs-idm19798128\">d) isopropyl alcohol (used in rubbing alcohol)<\/p>\r\n<p id=\"fs-idp1600928\">e) glycerine<\/p>\r\n2. Give the complete IUPAC name for each of the following compounds:\r\n<p id=\"fs-idm77966000\">a)<span id=\"fs-idp91536\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise3a_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H group. The C atom in the C H group is bonded above to an O H group. The C in the C H group is also bonded below to a C H subscript 2 group. The C H subscript 2 group is bonded below to a C H subscript 3 group.\" width=\"242\" height=\"154\" class=\"\" \/><\/span><\/p>\r\n<p id=\"fs-idm77997408\">b)<span id=\"fs-idm130287920\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise3b_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C atom. The C atom is bonded to an O H group and an I atom. It is also bonded to a second C atom. This second C atom is bonded above and below to a C H subscript 3 group. The second C atom is bonded to a C H subscript 2 group with is bonded to a C H subscript 3 group.\" width=\"256\" height=\"123\" class=\"\" \/><\/span><\/p>\r\n<p id=\"fs-idm36612192\">c)<span id=\"fs-idm152630560\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise3c_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H group. The C atom in the C H group is bonded to an O H group. The C H group is bonded to a C atom. The C atom is bonded below to a C l atom and above to a C H subscript 2 group. The C atom in the C H subscript 2 group is also bonded to a C H subscript 3 group. The C atom is also bonded to a C H subscript 2 group to the right. This C H subscript 2 group is bonded to another C H subscript 2 group. Below this second C H subscript 2 group a C H subscript 3 group is bonded.\" width=\"505\" height=\"163\" class=\"\" \/><\/span><\/p>\r\n3. Give the complete IUPAC name and the common name for each of the following compounds:\r\n<p id=\"fs-idp7086576\">a)<span id=\"fs-idp10202464\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4a_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to an O atom which is also bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscritp 3 group. All bonds are in a straight line.\" width=\"599\" height=\"47\" class=\"\" \/><\/span><\/p>\r\n<p id=\"fs-idm26630464\">b)<span id=\"fs-idm109423504\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4b_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to an O atom. This O atom is bonded to a C H subscript 2 group which is also bonded to another C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 3 group. All bonds are in a straight line.\" width=\"593\" height=\"52\" class=\"\" \/><\/span><\/p>\r\n<p id=\"fs-idm9894032\">c)<span id=\"fs-idm21271920\">\r\n<img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4c_img.jpg\" alt=\"This figure shows a C H subscript 3 group bonded to an O atom. This O atom is bonded to a C H subscript 2 group which is also bonded to another C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 3 group. All bonds are in a straight line.\" width=\"592\" height=\"51\" class=\"\" \/><\/span><\/p>\r\n<span id=\"fs-idm21271920\"><span style=\"font-size: 1em\">4. Name this molecule.<\/span><\/span>\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><a href=\"http:\/\/opentextbc.ca\/introductorychemistry\/wp-content\/uploads\/sites\/17\/2014\/07\/hal_and_alc_exc_8.png\"><img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/hal_and_alc_exc_8-1.png\" alt=\"hal_and_alc_exc_8\" class=\"alignnone size-full wp-image-2840\" height=\"85\" width=\"161\" \/><\/a><\/div>\r\n<div class=\"informalfigure large\"><span style=\"font-size: 1em\">5. Name this molecule.<\/span><\/div>\r\n<\/div>\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><a href=\"http:\/\/opentextbc.ca\/introductorychemistry\/wp-content\/uploads\/sites\/17\/2014\/07\/hal_and_alc_exc_9.png\"><img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/hal_and_alc_exc_9-1.png\" alt=\"hal_and_alc_exc_9\" class=\"alignnone size-full wp-image-2841\" height=\"89\" width=\"257\" \/><\/a><\/div>\r\n<div class=\"informalfigure large\"><span style=\"font-size: 1em\">6. Name this molecule.<\/span><\/div>\r\n<\/div>\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><a href=\"http:\/\/opentextbc.ca\/introductorychemistry\/wp-content\/uploads\/sites\/17\/2014\/07\/hal_and_alc_exc_10.png\"><img src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/hal_and_alc_exc_10-1.png\" alt=\"hal_and_alc_exc_10\" class=\"alignnone size-full wp-image-2842\" height=\"137\" width=\"179\" \/><\/a><\/div>\r\n<\/div>\r\n&nbsp;\r\n\r\n<strong>Answers<\/strong>\r\n<p id=\"fs-idp3456944\">1. a) ethyl alcohol, ethanol: CH<sub>3<\/sub>CH<sub>2<\/sub>OH; b) methyl alcohol, methanol: CH<sub>3<\/sub>OH; c) ethylene glycol, ethanediol: HOCH<sub>2<\/sub>CH<sub>2<\/sub>OH; d) isopropyl alcohol, 2-propanol: CH<sub>3<\/sub>CH(OH)CH<sub>3<\/sub>; e) glycerine, l,2,3-trihydroxypropane: HOCH<sub>2<\/sub>CH(OH)CH<sub>2<\/sub>OH<\/p>\r\n<p id=\"fs-idm30650800\">2. a) butan-2-ol; b) 2-iodo-3,3-dimethylpentan-2-ol; c) 3-chloro-3-ethylhexan-2-ol<\/p>\r\n3. a) 1-ethoxybutane, butyl ethyl ether; b) 1-ethoxypropane, ethyl propyl ether; c) 1-methoxypropane, methyl propyl ether\r\n\r\n4. 3-chloropentan-3-ol\r\n\r\n5.\u00a0<strong>\u00a0<\/strong>octan-4-ol\r\n\r\n6. 4-ethyl-2,5-dimethylhexan-3-ol\r\n\r\n<\/div>\r\n<\/section>\r\n<div>\r\n<h2>Glossary<\/h2>\r\n<strong>alcohol:\u00a0<\/strong>organic compound with a hydroxyl group (\u2013OH) bonded to a carbon atom\r\n\r\n<strong>ether:\u00a0<\/strong>organic compound with an oxygen atom that is bonded to two carbon atoms\r\n\r\n<\/div>","rendered":"<div>\n<div class=\"bcc-box bcc-highlight\">\n<h3>Learning Objectives<\/h3>\n<div>By the end of this section, you will be able to:<\/div>\n<div>\n<ul>\n<li>Describe the structure and properties of alcohols<\/li>\n<li>Describe the structure and properties of ethers<\/li>\n<li>Name and draw structures for alcohols and ethers<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<section id=\"fs-idm30613248\">\n<section id=\"fs-idm10005664\">\n<h2>Naming Alcohols<\/h2>\n<p id=\"fs-idm24572576\">The name of an alcohol comes from the hydrocarbon from which it was derived. The final <em>-e<\/em> in the name of the hydrocarbon is replaced by <em>-ol<\/em>, and the carbon atom to which the hydroxyl group (OH group) is bonded is indicated by a number placed before the name.<a class=\"footnote\" title=\"The IUPAC adopted new nomenclature guidelines in 2013 that require this number to be placed as an \u201cinfix\u201d rather than a prefix. For example, the new name for 2-propanol would be propan-2-ol. Widespread adoption of this new nomenclature will take some time, and students are encouraged to be familiar with both the old and new naming protocols.\" id=\"return-footnote-1922-1\" href=\"#footnote-1922-1\" aria-label=\"Footnote 1\"><sup class=\"footnote\">[1]<\/sup><\/a><\/p>\n<p id=\"fs-idp69169072\">Therefore when naming alcohols\u00a0following IUPAC, you follow the similar two rules for alkanes with modification to &#8220;rule 1&#8221; mentioned above.<\/p>\n<p><strong>Rule 1. Identify the longest chain of carbons which <span style=\"text-decoration: underline\">contains<\/span> the OH group and its position (PREFIX-#-AN<del>E<\/del>+OL). \u00a0<\/strong>And\u00a0when numbering the parent chain, the hydroxyl group gets the lowest possible number.<\/p>\n<p><strong>Rule 2. Names and position of the substituents.<\/strong><\/p>\n<p id=\"fs-idp8269216\">Alcohols containing two or more hydroxyl groups can be made. Examples include 1,2-ethanediol (ethylene glycol, used in antifreeze) and 1,2,3-propanetriol (glycerine, used as a solvent for cosmetics and medicines):<span id=\"fs-idm42427552\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_polyols_img.jpg\" alt=\"Structural formulas for 1 comma 2 dash ethanediol and 1 comma 2 comma 3 dash propanetriol are shown. The first structure has a two C atom hydrocarbon chain with an O H group attached to each carbon. The O H groups are shown in red an each O atom has two sets of electron dots. Each C atom also has two H atoms bonded to it. The second structure shows a three C atom hydrocarbon chain with an O H group bonded to each carbon. The O H groups are shown in red, and each O atom has two sets of electron dots. The first C atom has two H atoms bonded to it. The second C atom has one H atom bonded to it. The third C atom has two H atoms bonded to it.\" class=\"aligncenter\" width=\"446\" height=\"210\" \/><\/span><\/p>\n<div class=\"example textbox shaded\" id=\"fs-idm9024448\">\n<h3>Example 1<\/h3>\n<p id=\"fs-idp1577984\">Consider the following example. How should it be named?<span id=\"fs-idm20720800\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_alcohol1_img.jpg\" alt=\"A molecular structure of a hydrocarbon chain with a length of five C atoms is shown. The first C atom (from left to right) is bonded to three H atoms. The second C atom is bonded on one H atom and an O atom which is also bonded to an H atom. The O atom has two sets of electron dots. The third C atom is bonded to two H atoms. The fourth C atom is bonded to two H atoms. The fifth C atom is bonded to three H atoms. All bonds shown are single.\" width=\"501\" height=\"154\" class=\"aligncenter\" \/><\/span><\/p>\n<p id=\"fs-idp3540976\"><strong>Solution<\/strong><br \/>\nThe carbon chain contains five carbon atoms. If the hydroxyl group was not present, we would have named this molecule pentane. To address the fact that the hydroxyl group is present, we change the ending of the name to <em>-ol<\/em>. In this case, since the \u2013OH is attached to carbon 2 in the chain, we would name this molecule 2-pentanol.<\/p>\n<p>&nbsp;<\/p>\n<p id=\"fs-idm65417856\"><em><strong>Test Yourself<\/strong><\/em><br \/>\nName the following molecule:<span id=\"fs-idm39569728\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_alcohol2_img.jpg\" alt=\"The structure shown has a C H subscript 3 group bonded up and to the right to a C atom. The C atom is bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded down and to the right to a C H subscript 3 group. The second C atom (from left to right) is bonded to a C H subscript 3 group and an O H group.\" width=\"272\" height=\"93\" class=\"aligncenter\" \/><\/span><\/p>\n<p><em><strong>Answer<\/strong><\/em><\/p>\n<p>2-methylpentan-2-ol<\/p>\n<\/div>\n<\/section>\n<\/section>\n<section id=\"fs-idm24652464\">\n<h2>Naming Ethers<\/h2>\n<p id=\"fs-idp6654240\"><strong>Ethers<\/strong> are compounds that contain the functional group \u2013O\u2013. Ethers do not have a designated suffix like the other types of molecules we have named so far. In the IUPAC system, the oxygen atom and the smaller carbon branch are named as an alkoxy substituent and the remainder of the molecule as the base chain, as in alkanes. As shown in the following compound, the red symbols represent the smaller alkyl group and the oxygen atom, which would be named \u201cmethoxy.\u201d The larger carbon branch would be ethane, making the molecule methoxyethane. Many ethers are referred to with common names instead of the IUPAC system names. For common names, the two branches connected to the oxygen atom are named separately and followed by \u201cether.\u201d \u00a0But if the two alkyl groups are the same, then the di prefix is used. The common name for methoxyethane shown below is ethylmethyl ether:<span id=\"fs-idm6486336\"><br \/>\n<\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_NameEthers_img.jpg\" alt=\"A molecular structure is shown with a red C H subscript 3 group bonded up and to the right to a red O atom. The O atom is bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to a C H subscript 3 group.\" class=\"aligncenter\" width=\"299\" height=\"57\" \/><\/p>\n<p id=\"fs-idp69169072\">Therefore when naming ethers, the two rules are modified. \u00a0And furthermore, there are two ways that are commonly used: IUPAC method and the common method.<\/p>\n<p><strong>IUPAC method of naming ethers:<\/strong><\/p>\n<p><strong>Rule 1. Identify the longest carbon branch\u00a0(PREFIX-ANE).<\/strong><\/p>\n<p><strong>Rule 2. Names of the substituent, the other carbon branch (PREFIX+OXY)<\/strong><\/p>\n<p>&nbsp;<\/p>\n<p><strong>Common method of naming ethers:<\/strong><\/p>\n<p><strong>ALKYLALKYL ether \u00a0 \u00a0or \u00a0 diALKYL ether<\/strong><\/p>\n<\/section>\n<p>&nbsp;<\/p>\n<p>For example, the following ether would be commonly named ethylpropyl ether. \u00a0its name following the IUPAC rules would be ethoxypropane.<\/p>\n<p><span id=\"fs-idm109423504\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4b_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to an O atom. This O atom is bonded to a C H subscript 2 group which is also bonded to another C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 3 group. All bonds are in a straight line.\" class=\"aligncenter\" width=\"604\" height=\"53\" \/><\/span><\/p>\n<section id=\"fs-idm24652464\">\n<div class=\"example textbox shaded\" id=\"fs-idm48177328\">\n<h3>Example 2<\/h3>\n<p id=\"fs-idm86150048\">Provide the IUPAC and common name for the ether shown here:<span id=\"fs-idp882608\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_ethers1_img.jpg\" alt=\"A molecular structure shows a C H subscript 3 group bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to an O atom. The O atom is bonded down and to the right to a C H subscript 2 group. The C H subscript 2 group is bonded up and to the right to a C H subscript 3 group.\" class=\"aligncenter\" width=\"289\" height=\"57\" \/><\/span><\/p>\n<p>&nbsp;<\/p>\n<p id=\"fs-idm451728\"><strong>Solution<\/strong><br \/>\nIUPAC: The molecule is made up of an ethoxy group attached to an ethane chain, so the IUPAC name would be ethoxyethane.<\/p>\n<p id=\"fs-idp1988576\">Common: The groups attached to the oxygen atom are both ethyl groups, so the common name would be diethyl ether.<\/p>\n<p>&nbsp;<\/p>\n<p id=\"fs-idm81417584\"><em><strong>Test Yourself<\/strong><\/em><br \/>\nProvide the IUPAC and common name for the ether shown:<span id=\"fs-idp6957760\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_ethers2_img.jpg\" alt=\"A molecular structure shows a C H subscript 3 group bonded up and to the right to an O atom. The O atom is bonded down and to the right to a C H group. The C H group is bonded up and to the right to a C H subscript 3 group. The C H group is also bonded down and to the right to another C H subscript 3 group.\" width=\"262\" height=\"92\" class=\"aligncenter\" \/><\/span><\/p>\n<p><em><strong>Answers<\/strong><\/em><\/p>\n<p>IUPAC: 2-methoxypropane; common: isopropylmethyl ether<\/p>\n<\/div>\n<div id=\"fs-idm85442272\" class=\"note chemistry link-to-learning textbox shaded\">\n<p><span id=\"fs-idm86050336\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/OSC_Interactive_200-40.png\" alt=\"\u00a0\" class=\"alignleft\" width=\"113\" height=\"70\" \/><br \/>\n<\/span><\/p>\n<p id=\"fs-idp6043376\">Want more practice naming ethers? This brief <a href=\"http:\/\/openstaxcollege.org\/l\/16ethers\">video review<\/a> summarizes the nomenclature for ethers.<\/p>\n<\/div>\n<div id=\"fs-idp6839408\" class=\"note chemistry everyday-life textbox shaded\">\n<h3 class=\"title\">Carbohydrates and Diabetes<\/h3>\n<p id=\"fs-idm73541184\">Carbohydrates are large biomolecules made up of carbon, hydrogen, and oxygen. The dietary forms of carbohydrates are foods rich in these types of molecules, like pastas, bread, and candy. The name \u201ccarbohydrate\u201d comes from the formula of the molecules, which can be described by the general formula C<sub>m<\/sub>(H<sub>2<\/sub>O)<sub>n<\/sub>, which shows that they are in a sense \u201ccarbon and water\u201d or \u201chydrates of carbon.\u201d In many cases, <em>m<\/em> and <em>n<\/em> have the same value, but they can be different. The smaller carbohydrates are generally referred to as \u201csugars,\u201d the biochemical term for this group of molecules is \u201csaccharide\u201d from the Greek word for sugar (<a href=\"#CNX_Chem_20_02_Sugars\" class=\"autogenerated-content\">Figure 1<\/a>). Depending on the number of sugar units joined together, they may be classified as monosaccharides (one sugar unit), disaccharides (two sugar units), oligosaccharides (a few sugars), or polysaccharides (the polymeric version of sugars\u2014polymers were described in the feature box earlier in this chapter on recycling plastics). The scientific names of sugars can be recognized by the suffix <em>-ose<\/em> at the end of the name (for instance, fruit sugar is a monosaccharide called \u201cfructose\u201d and milk sugar is a disaccharide called lactose composed of two monosaccharides, glucose and galactose, connected together). Sugars contain some of the functional groups we have discussed: Note the alcohol groups present in the structures and how monosaccharide units are linked to form a disaccharide by formation of an ether.<\/p>\n<figure id=\"CNX_Chem_20_02_Sugars\">\n<figure style=\"width: 1200px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_sugars.jpg\" alt=\"This figure shows structural and ball-and-stick models for the common sugars fructose and lactose. Carbon atoms are illustrated in black, oxygen atoms are red, and hydrogen atoms are white in the ball-and-stick models.\" width=\"1200\" height=\"755\" \/><figcaption class=\"wp-caption-text\"><strong>Figure 1.<\/strong> The illustrations show the molecular structures of fructose, a five-carbon monosaccharide, and of lactose, a disaccharide composed of two isomeric, six-carbon sugars.<\/figcaption><\/figure>\n<\/figure>\n<p id=\"fs-idm33645104\">Organisms use carbohydrates for a variety of functions. Carbohydrates can store energy, such as the polysaccharides glycogen in animals or starch in plants. They also provide structural support, such as the polysaccharide cellulose in plants and the modified polysaccharide chitin in fungi and animals. The sugars ribose and deoxyribose are components of the backbones of RNA and DNA, respectively. Other sugars play key roles in the function of the immune system, in cell-cell recognition, and in many other biological roles.<\/p>\n<p id=\"fs-idm20354000\">Diabetes is a group of metabolic diseases in which a person has a high sugar concentration in their blood (<a href=\"#CNX_Chem_20_02_Diabetes\" class=\"autogenerated-content\">Figure 2<\/a>). Diabetes may be caused by insufficient insulin production by the pancreas or by the body\u2019s cells not responding properly to the insulin that is produced. In a healthy person, insulin is produced when it is needed and functions to transport glucose from the blood into the cells where it can be used for energy. The long-term complications of diabetes can include loss of eyesight, heart disease, and kidney failure.<\/p>\n<p id=\"fs-idm13367296\">In 2013, it was estimated that approximately 3.3% of the world\u2019s population (~380 million people) suffered from diabetes, resulting in over a million deaths annually. Prevention involves eating a healthy diet, getting plenty of exercise, and maintaining a normal body weight. Treatment involves all of these lifestyle practices and may require injections of insulin.<\/p>\n<figure id=\"CNX_Chem_20_02_Diabetes\">\n<figure style=\"width: 800px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_diabetes.jpg\" alt=\"This is a diagram of a hand with a blood droplet on an index finger and a nearby sharp pointed pen-like object. The finger is next shown touching a white and green test strip with arrows pointing to the green region where the bloody finger touches the strip. An arrow points to a small rectangular device in which the green end of the strip is inserted. An L C D display provides a reading.\" width=\"800\" height=\"600\" \/><figcaption class=\"wp-caption-text\"><strong>Figure 2.<\/strong> Diabetes is a disease characterized by high concentrations of glucose in the blood. Treating diabetes involves making lifestyle changes, monitoring blood-sugar levels, and sometimes insulin injections. (credit: \u201cBlausen Medical Communications\u201d\/Wikimedia Commons)<\/figcaption><\/figure>\n<\/figure>\n<\/div>\n<\/section>\n<section id=\"fs-idm82374704\" class=\"summary\">\n<h2>Key Concepts and Summary<\/h2>\n<p id=\"fs-idm8778416\">Many organic compounds that are not hydrocarbons can be thought of as derivatives of hydrocarbons. A hydrocarbon derivative can be formed by replacing one or more hydrogen atoms of a hydrocarbon by a functional group, which contains at least one atom of an element other than carbon or hydrogen. The properties of hydrocarbon derivatives are determined largely by the functional group. The \u2013OH group is the functional group of an alcohol. The \u2013R\u2013O\u2013R\u2013 group is the functional group of an ether.<\/p>\n<p>The systematic methods of naming alcohols follow a similar procedure and the names have three main parts:<\/p>\n<p><span style=\"color: #0000ff\"><strong>1)<\/strong><\/span> specifying the information about the substituents,<\/p>\n<p><span style=\"background-color: #ffff00\"><strong>2)<\/strong><\/span> specifying the information about the parent chain, and<\/p>\n<p><span style=\"color: #008000\"><strong>3)<\/strong><\/span> the ending which specifies what functional group is present in the structure being named.<\/p>\n<p><strong>Alcohols: \u00a0 \u00a0<span style=\"color: #0000ff\">#-substituents<\/span>&#8211;<span style=\"background-color: #ffff00\">PREFIX<\/span>&#8211;<span style=\"color: #008000\">#-AN<del>E<\/del>+OL<\/span><\/strong><\/p>\n<p><strong>Ethers: \u00a0 \u00a0<span style=\"color: #0000ff\">PREFIX+OXY<\/span>&#8211;<span style=\"background-color: #ffff00\">PREFIX<\/span>&#8211;<span style=\"color: #008000\">ANE<\/span><\/strong><\/p>\n<p>Remember: there are two ways that are commonly used to name ethers. \u00a0The common method is also important to know.<\/p>\n<p><strong>Common method of naming ethers:<\/strong><\/p>\n<p><strong>ALKYLALKYL <span style=\"color: #008000\">ether<\/span> \u00a0 \u00a0or \u00a0 diALKYL <span style=\"color: #008000\">ether<\/span><\/strong><\/p>\n<\/section>\n<section id=\"fs-idm77059568\" class=\"exercises\">\n<div class=\"bcc-box bcc-info\">\n<h3>Exercises<\/h3>\n<p>1. Write condensed formulas and provide IUPAC names for the following compounds:<\/p>\n<p id=\"fs-idm81589984\">a) ethyl alcohol (in beverages)<\/p>\n<p id=\"fs-idm401696\">b) methyl alcohol (used as a solvent, for example, in shellac)<\/p>\n<p id=\"fs-idm31515088\">c) ethylene glycol (antifreeze)<\/p>\n<p id=\"fs-idm19798128\">d) isopropyl alcohol (used in rubbing alcohol)<\/p>\n<p id=\"fs-idp1600928\">e) glycerine<\/p>\n<p>2. Give the complete IUPAC name for each of the following compounds:<\/p>\n<p id=\"fs-idm77966000\">a)<span id=\"fs-idp91536\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise3a_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H group. The C atom in the C H group is bonded above to an O H group. The C in the C H group is also bonded below to a C H subscript 2 group. The C H subscript 2 group is bonded below to a C H subscript 3 group.\" width=\"242\" height=\"154\" class=\"\" \/><\/span><\/p>\n<p id=\"fs-idm77997408\">b)<span id=\"fs-idm130287920\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise3b_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C atom. The C atom is bonded to an O H group and an I atom. It is also bonded to a second C atom. This second C atom is bonded above and below to a C H subscript 3 group. The second C atom is bonded to a C H subscript 2 group with is bonded to a C H subscript 3 group.\" width=\"256\" height=\"123\" class=\"\" \/><\/span><\/p>\n<p id=\"fs-idm36612192\">c)<span id=\"fs-idm152630560\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise3c_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H group. The C atom in the C H group is bonded to an O H group. The C H group is bonded to a C atom. The C atom is bonded below to a C l atom and above to a C H subscript 2 group. The C atom in the C H subscript 2 group is also bonded to a C H subscript 3 group. The C atom is also bonded to a C H subscript 2 group to the right. This C H subscript 2 group is bonded to another C H subscript 2 group. Below this second C H subscript 2 group a C H subscript 3 group is bonded.\" width=\"505\" height=\"163\" class=\"\" \/><\/span><\/p>\n<p>3. Give the complete IUPAC name and the common name for each of the following compounds:<\/p>\n<p id=\"fs-idp7086576\">a)<span id=\"fs-idp10202464\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4a_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to an O atom which is also bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscritp 3 group. All bonds are in a straight line.\" width=\"599\" height=\"47\" class=\"\" \/><\/span><\/p>\n<p id=\"fs-idm26630464\">b)<span id=\"fs-idm109423504\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4b_img.jpg\" alt=\"This shows a C H subscript 3 group bonded to a C H subscript 2 group. This C H subscript 2 group is bonded to an O atom. This O atom is bonded to a C H subscript 2 group which is also bonded to another C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 3 group. All bonds are in a straight line.\" width=\"593\" height=\"52\" class=\"\" \/><\/span><\/p>\n<p id=\"fs-idm9894032\">c)<span id=\"fs-idm21271920\"><br \/>\n<img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/CNX_Chem_20_02_Exercise4c_img.jpg\" alt=\"This figure shows a C H subscript 3 group bonded to an O atom. This O atom is bonded to a C H subscript 2 group which is also bonded to another C H subscript 2 group. This C H subscript 2 group is bonded to a C H subscript 3 group. All bonds are in a straight line.\" width=\"592\" height=\"51\" class=\"\" \/><\/span><\/p>\n<p><span id=\"fs-idm21271920\"><span style=\"font-size: 1em\">4. Name this molecule.<\/span><\/span><\/p>\n<div class=\"question\">\n<div class=\"informalfigure large\"><a href=\"http:\/\/opentextbc.ca\/introductorychemistry\/wp-content\/uploads\/sites\/17\/2014\/07\/hal_and_alc_exc_8.png\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/hal_and_alc_exc_8-1.png\" alt=\"hal_and_alc_exc_8\" class=\"alignnone size-full wp-image-2840\" height=\"85\" width=\"161\" \/><\/a><\/div>\n<div class=\"informalfigure large\"><span style=\"font-size: 1em\">5. Name this molecule.<\/span><\/div>\n<\/div>\n<div class=\"question\">\n<div class=\"informalfigure large\"><a href=\"http:\/\/opentextbc.ca\/introductorychemistry\/wp-content\/uploads\/sites\/17\/2014\/07\/hal_and_alc_exc_9.png\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/hal_and_alc_exc_9-1.png\" alt=\"hal_and_alc_exc_9\" class=\"alignnone size-full wp-image-2841\" height=\"89\" width=\"257\" \/><\/a><\/div>\n<div class=\"informalfigure large\"><span style=\"font-size: 1em\">6. Name this molecule.<\/span><\/div>\n<\/div>\n<div class=\"question\">\n<div class=\"informalfigure large\"><a href=\"http:\/\/opentextbc.ca\/introductorychemistry\/wp-content\/uploads\/sites\/17\/2014\/07\/hal_and_alc_exc_10.png\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-content\/uploads\/sites\/387\/2018\/04\/hal_and_alc_exc_10-1.png\" alt=\"hal_and_alc_exc_10\" class=\"alignnone size-full wp-image-2842\" height=\"137\" width=\"179\" \/><\/a><\/div>\n<\/div>\n<p>&nbsp;<\/p>\n<p><strong>Answers<\/strong><\/p>\n<p id=\"fs-idp3456944\">1. a) ethyl alcohol, ethanol: CH<sub>3<\/sub>CH<sub>2<\/sub>OH; b) methyl alcohol, methanol: CH<sub>3<\/sub>OH; c) ethylene glycol, ethanediol: HOCH<sub>2<\/sub>CH<sub>2<\/sub>OH; d) isopropyl alcohol, 2-propanol: CH<sub>3<\/sub>CH(OH)CH<sub>3<\/sub>; e) glycerine, l,2,3-trihydroxypropane: HOCH<sub>2<\/sub>CH(OH)CH<sub>2<\/sub>OH<\/p>\n<p id=\"fs-idm30650800\">2. a) butan-2-ol; b) 2-iodo-3,3-dimethylpentan-2-ol; c) 3-chloro-3-ethylhexan-2-ol<\/p>\n<p>3. a) 1-ethoxybutane, butyl ethyl ether; b) 1-ethoxypropane, ethyl propyl ether; c) 1-methoxypropane, methyl propyl ether<\/p>\n<p>4. 3-chloropentan-3-ol<\/p>\n<p>5.\u00a0<strong>\u00a0<\/strong>octan-4-ol<\/p>\n<p>6. 4-ethyl-2,5-dimethylhexan-3-ol<\/p>\n<\/div>\n<\/section>\n<div>\n<h2>Glossary<\/h2>\n<p><strong>alcohol:\u00a0<\/strong>organic compound with a hydroxyl group (\u2013OH) bonded to a carbon atom<\/p>\n<p><strong>ether:\u00a0<\/strong>organic compound with an oxygen atom that is bonded to two carbon atoms<\/p>\n<\/div>\n<hr class=\"before-footnotes clear\" \/><div class=\"footnotes\"><ol><li id=\"footnote-1922-1\"> The IUPAC adopted new nomenclature guidelines in 2013 that require this number to be placed as an \u201cinfix\u201d rather than a prefix. For example, the new name for 2-propanol would be propan-2-ol. Widespread adoption of this new nomenclature will take some time, and students are encouraged to be familiar with both the old and new naming protocols. <a href=\"#return-footnote-1922-1\" class=\"return-footnote\" aria-label=\"Return to footnote 1\">&crarr;<\/a><\/li><\/ol><\/div>","protected":false},"author":330,"menu_order":5,"template":"","meta":{"pb_show_title":"on","pb_short_title":"10.4 Nomenclature of Alcohols and Ethers","pb_subtitle":"","pb_authors":[],"pb_section_license":"cc-by-nc-sa"},"chapter-type":[],"contributor":[],"license":[54],"class_list":["post-1922","chapter","type-chapter","status-publish","hentry","license-cc-by-nc-sa"],"part":1829,"_links":{"self":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/1922","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/users\/330"}],"version-history":[{"count":20,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/1922\/revisions"}],"predecessor-version":[{"id":4840,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/1922\/revisions\/4840"}],"part":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/parts\/1829"}],"metadata":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/1922\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/media?parent=1922"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapter-type?post=1922"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/contributor?post=1922"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/license?post=1922"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}