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1.
2.
What is the hybridization of carbon atoms labeled i iii in the following structure?
H
H2C
i
a.
b.
c.
d.
C
ii
CH3
iii
3.
4.
a.
b.
c.
d.
5.
a.
b.
c.
d.
6.
2-methylenepentane
2-methyl-1-pentene
2-vinylpentane
2-propyl-1-propene
(E)-3-methyl-4-hexene
(Z)-3-methyl-4-hexene
(E)-4-methyl-2-hexene
(Z)-4-methyl-2-hexene
a.
b.
c.
d.
7.
a.
b.
c.
d.
8.
2-methyl-4-vinyl-2-pentene
3,5-dimethyl-1,4-hexadiene
2,4-dimethyl-3,5-hexadiene
1,1,3-trimethyl-1,4-pentadiene
(Z)-3-ethyl-5-methyl-1,4-heptadiene
(E)-3-ethyl-5-methyl-1,4-heptadiene
(E)-3-methyl-5-vinyl-3-heptene
(Z)-1,3-diethyl-1-methyl-1,4-pentadiene
9.
What is the major organic product obtained from the following reaction?
H2 O
H2SO4
HO
OH
OH
1
a.
b.
c.
d.
10.
OH
2
1
2
3
4
What is the major organic product obtained from the following reaction?
O
O
+
H
1. OsO4
OH
2
2. NaHSO3
H2O
OH
3
OH
OH
a.
b.
c.
d.
11.
1
2
3
4
What is the major organic product obtained from the following reaction?
CH3
HO
HO
CH3
CH3
H3C
OH
OH
O
OH
1. OsO4
CH3
2. NaHSO3
H2O
a.
b.
c.
d.
12.
1
2
3
4
What is the major organic product obtained from the following reaction?
CH3
HO
HO
CH3
CH3
OH
H3C
OH
O
OH
1. O3
H
CH3
2. (CH3)2S
O
1
a.
b.
c.
d.
13.
1
2
3
4
What is (are) the major organic product(s) obtained from the following reaction?
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
H2
Pt
a.
b.
c.
d.
14.
only 1
only 2
only 3
only 2 and 3
What is (are) the major organic product(s) obtained from the following reaction?
Br2
1 2,3-dibromobutane
2 2,2-dibromobutane
3 3,3-dibromobutane
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
15.
What is (are) the major organic product(s) obtained from the following reaction?
Br2
1 2,3-dibromobutane
2 2,2-dibromobutane
3 3,3-dibromobutane
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
16.
What is (are) the major organic product(s) obtained from the following reaction?
1. OsO4
2. NaHSO3
H2O
1 2,3-butanediol
2 2,2-butanediol
3 3 ,3-butanediol
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
17.
What is (are) the major organic product(s) obtained from the following reaction?
1. OsO4
2. NaHSO3
H2O
1 2,3-butanediol
2 2,2-butanediol
3 3 ,3-butanediol
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
18.
What is the major organic product obtained from the following reaction?
H2O
H2SO4
OH
OH
OH
OH
2
19.
a.
b.
c.
d.
2
3
4
a.
b.
c.
d.
20.
H2O, H2SO4
H2SO4
O2
OsO4; followed by NaHSO3
a.
b.
c.
d.
21.
OH
a.
b.
c.
d.
22.
H2O, H2SO4
H2SO4
O2
OsO4; followed by NaHSO3
What type of reactive intermediate is formed in the reaction of an alkene with HBr to
give a bromoalkane?
a.
carbocation
b.
carbanion
c.
radical
d.
cyclic bromonium ion
23.
What type of reaction mechanism accounts for the reaction of an alkene with
aqueous acid to give an alcohol?
a.
nucleophilic addition
b.
electrophilic addition
c.
radical addition
d.
elimination
24.
a.
b.
c.
d.
25.
primary
secondary
tertiary
quaternary
What is the major organic product obtained from the following reaction?
HBr
Br
Br
Br
1
a.
b.
c.
d.
26.
1
2
3
4
What is the correct order of stability of the following carbocations (more stable > less
stable)?
a.
b.
c.
d.
27
Br
1>2>3
1>3>2
3>1>2
3>2>1
What is (are) the major organic product(s) obtained from the following reaction?
HBr
1 (R)-2-bromo-3-methylbutane
2 (S)-2-bromo-3-methylbutane
3 2-bromo-2-methylbutane
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
28.
29.
30.
What is the major organic product obtained from the following reaction?
H2 O
O
H2SO4
OH
OH
OH
1
a.
1
b.
2
c.
3
d.
4
Predict the products of each reaction below.
stereochemistry when relevant.
31.
CH3
H2
a)
Pd
CH3
b)
CH3
Cl2
CCl4
1. O3, CH2Cl2
2. Zn, HOAc
c)
CH3
KMnO4
d)
e)
32.
H3O+
Br
KOH
ethanol
Choose the best reagent from the list below for carrying out each transformation.
Place the letter of the reagent in the blank to the left of the reaction.
a. 1. O3
2. Zn, H3O+
c. 1. OsO4
2. NaHSO3, H2O
b. CH3COOOH
d.
i)
CH3
O
H
CH3
O
CH3
CH3
ii)
H
CH3
OH
CH3
iii)
34.
a)
b)
For each reaction below suggest structures for alkenes that give the indicated
reaction products. There may be more than one answer in some cases.
H2
Pd
1. H2O, H2SO4
1. BH3, THF
2. H2O2, NaOH, H2O
OH
c)
Br
HBr
ether
d)
ROOR
heat
( CH2CHCH2CHCH2CH )n
C6H5 C6H5 C6H5