Chapter 10. Organic Chemistry

10.8 End of Chapter Problems

1. Draw the line bond structure for the following compounds:

a) Br[CH(CH3)]4COCH(CH3)CH2CH3



d) (HO)2CH(CH2)2O(CH2)3COOH

2. For the following compounds, give the chemical formula and the condensed structure:

3. Answer the following questions for each of these compounds.

a) Name the circled functional groups: A = ?,  B = ?, C = ?

b) What is the chemical formula of the compound?

c) How many lone pairs are there in the compound?

Phenylalanine is an α-amino acid.

Aspirin, also known as acetylsalicylic acid, is often used to relieve minor aches and pains, and to reduce fever.

Tetracycline is an antibiotic used against many bacterial infections.

Ampicillin is an antibiotic used against many bacterial infections since 1961.

Forskolin is a natural product produced by the Indian Coleus plant (Coleus forskohlii).

4. Cycloalkanes are named based on the number of C atoms in them, just like regular alkanes, but with the prefix cyclo– on the name. What are the names of the three smallest cycloalkanes?

5. Draw the bond-line structure of all noncyclic alkanes with only four C atoms.

6. Cyclic alkanes can also have substituent groups on the ring. Draw the bond-line structure of all cyclic alkanes with only four C atoms.

7. What is the maximum number of methyl groups that can be on a propane backbone before the molecule cannot be named as a propane compound?

8. In the gasoline industry, what is called isooctane is actually 2,2,4-trimethylpentane. Draw the structure of isooctane.

9. The actual name for the explosive TNT is 2,4,6-trinitrotoluene. If the structure of TNT is as shown below, propose the structure of the parent compound toluene.

10. Draw the smallest molecule that can have a separate aldehyde and carboxylic acid group.
11. Name the functional group(s) in the following structure:
12. Ethyl acetate is a common ingredient in nail-polish remover because it is a good solvent. Its IUPAC name is ethyl ethanoate.  Draw the structure of ethyl acetate.
13. Draw the structure of diethyl ether, once used as an anesthetic.
14. Write the chemical reaction of HCl with trimethylamine.
15.Give the IUPAC name the following organic compounds.



2.  a) C8H12O4      HOOCCH2COCH2CO(CH2)2CH3

b) C8H10O3         HOC(CH)4(CH2)2COOH

c) C14H28              CH3(CH)2CH(CH[CH3]CH2CH3)(CH2)5CH3

d) C9H17Cl        Cl(CH2)2C(CHCH2CH3)(CH2)2CH3

3. Phenylalanine a) A = Arene, B = Carboxylic Acid, C = Primary Amine

b) C9H11NO2

c) 5 lone pairs – one on the nitrogen and two on each oxygen,

Aspirin a) A = Ester, B = Arene, C = Carboxylic Acid

b) C9H8O4

c) 8 lone pairs – two on each oxygen,

Tetracycline a) A = Tertiary Alcohol, B = Tertiary Amine, C = Ketone

b) C22H24N2O8

c) 18 lone pairs – one on each nitrogen and two on each oxygen

Ampicillin  a) A = Tertiary Amide, B = Carboxylic Acid, C = Arene

b) C16H19N3O4S

c) 13 lone pairs – one on each nitrogen, two on each oxygen and two on the sulfur

Forskolin a) A = Secondary Alcohol, B = Ether, C = Ketone

b) C22H34O7

c) 14 lone pairs –two on each oxygen,

4. cyclopropane, cyclobutane, and cyclopentane




7. two









11. alcohol (or more specifically phenol), arene, ketone, primary amine





14. Triethylamine is a base and HCl is an acid, therefore you get an acid-base reaction.

(CH3)3N + HCl [latex]\longrightarrow[/latex] (CH3)3NHCl

15. a) 4-ethyloctane          b) 3-ethyl-2,4-dimethylhexane

c) 2,4-dibromo-1-chloro-3-methylpentane        d) 5,5-dimethyl-3-propyl-1-heptene

e) 4-methyl-4-octene      f)  2-ethyl-1,6-heptadiene       g) 3-ethyl-1,4-hexadiene

h) 4-ethyl-2,5-octadiene     i) 3,3-dimethyl-4-octyne       j) 4-methyl-2-hexyne


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CHEM 1114 - Introduction to Chemistry by Shirley Wacowich-Sgarbi is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.

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