Chapter 3 - Organic Compounds: Alkanes and Their Stereochemistry

MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.

O CH3 O
O CH3
A. H B. CH3CHCH C. D.
H
NH2 Cl
H3C CH3

O
Cl CH3
E. F. CH3CHCH3 G. H

H
CH3

1. is an amino aldehyde.

Answer: B

2. is an aromatic ketone.

Answer: E

3. is a tertiary chloride.

Answer: C

4. is a cyclic alkane with two cis methyl groups.

Answer: C

5. Circle and name each functional group in the following structure.

O
O
O
O OH

O
cortisone acetate (active ingredient in steriod skin cream)

12 Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry

 Answer: O
ketone O ester
O
ketone O OH
alcohol

H
ketone
O
alkene

Label the indicated atoms in the structure below as 1°, 2°, 3°, or 4°.
O

7. O
O
HO OH
6. 9.

H 8.
O

6. This atom is .
Answer: 4°

7. This atom is .
Answer: 2°

8. This atom is .
Answer: 3°

9. This atom is .
Answer: 1°

Label the following pairs of compounds as:

a. identical
b. constitutional isomers
c. neither

Place the letter of the correct answer in the blank below the structures.
O

10. H
and

Answer: b

Test Items for McMurry’s Organic Chemistry, Seventh Edition 13

11.
CH3 CH2CH3

and

H3C CH3

Answer: c

CH3
12.
and CH3

Answer: a

Provide proper IUPAC names for each compound below.

13. (CH3)2CHCH2CH2CH(CH2CH3)CH2C(CH3)3

Answer: 4-ethyl-2,2,7-trimethyloctane

14.
Br CH3

H3CCHCH2CCH2CHCH2CH3

CH3 C(CH3)3

Answer: 7-bromo-3-ethyl-2,2,5,5-tetramethyloctane or 2-bromo-6-tert-butyl-4,4-dimethyloctane

CH2CH2CH3

15. CH3CHCH2CHCHCH3

CH2CH3 CH3

Answer: 5-isopropyl-3-methyloctane

14 Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry

Consider the representation below to answer the following questions.

Z.

16. Provide the IUPAC name for compound Z.

Answer: 5-ethyl-3,4-dimethyloctane

Draw structures corresponding to each of the following names.

17. 4-isopropyl-6-ethyldecane

Answer:

18. 2-fluoro-3-methylpentane

Answer:

19. 4-(2,2-dibromoethyl)-3,5-dichloroheptane

Br

Br
Answer:

Cl Cl

Test Items for McMurry’s Organic Chemistry, Seventh Edition 15

Experiments have shown that for 1,2-dichloroethane, ClCH2CH2Cl, in carbon tetrachloride solution at 25° C,
70% of the molecules are in the anti and 30% are in the gauche conformation.

20. Draw a Newman projection of the anti conformation of 1,2-dichloroethane.

Answer:
Cl
H H

H H
Cl

21. Draw a Newman projection of the gauche conformation of 1,2-dichloroethane.

Answer: Cl
H Cl

H H
H

Cipro® (Ciprofloxacin) is a synthetic broad spectrum antibacterial agent. It was most recently in the news as
the antibiotic of choice for the treatment of anthrax. The structure of Cipro is shown below.

O
O
F C OH

N N Cipro

N
H

22. Circle the functional groups in the Cipro representation above.

Answer:
O
O
F C OH

N N
N
H

16 Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry

Predict the hybridization of the indicated atoms in Cipro.
24.
O O

23. F C OH

N N 25.

N
H

23. The hybridization of this nitrogen atom is __________.

Answer: sp3

24. The hybridization of this carbon atom is __________.

Answer: sp2

25. The hybridization of this carbon atom is __________.

Answer: sp3

26. Put a box around the most polar bond in Cipro based on electronegativity values.
O
O
F C OH

N N Cipro

N
H

Answer:
O
O
F C OH

N N
N
H

Test Items for McMurry’s Organic Chemistry, Seventh Edition 17