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
A.
CH3
O
H
B. CH3CHCH
C.
D.
H
NH2
H3C
O
CH3
Cl
O
CH3
Cl
E.
F. CH3CHCH3
CH3
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
OH
O
H
O
cortisone acetate (active ingredient in steriod skin cream)
12
Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
Answer:
O
ketone O
ester
O
OH
ketone O
alcohol
H
ketone
O
alkene
Label the indicated atoms in the structure below as 1°, 2°, 3°, or 4°.
O
O
7.
O
OH
HO
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.
b.
c.
identical
constitutional isomers
neither
Place the letter of the correct answer in the blank below the structures.
O
10.
H
and
O
Answer:
b
Test Items for McMurry’s Organic Chemistry, Seventh Edition
13
11.
CH3
CH2CH3
and
H3C
Answer:
CH3
c
CH3
12.
and
Answer:
CH3
a
Provide proper IUPAC names for each compound below.
13. (CH3)2CHCH2CH2CH(CH2CH3)CH2C(CH3)3
Answer:
14.
Br
4-ethyl-2,2,7-trimethyloctane
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:
14
5-isopropyl-3-methyloctane
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:
F
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
N
OH
Cipro
N
N
H
22. Circle the functional groups in the Cipro representation above.
Answer:
O
F
N
O
C
OH
N
N
H
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Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
Predict the hybridization of the indicated atoms in Cipro.
O
F
23.
C
N
24.
O
OH
25.
N
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
F
N
O
C
OH
Cipro
N
N
H
Answer:
O
F
N
O
C
OH
N
N
H
Test Items for McMurry’s Organic Chemistry, Seventh Edition
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