Download 1. Identify the tertiary alcohol(s). A B C CH3CHCH2CH(CH3)2

Identify the tertiary alcohol(s).
CH3CH2CHCH(CH3)2
CH3CHCH2CH(CH3)2
CH3CH2CH2C(CH3)2
OH
OH
A
only A
only B
only C
both A and C
B
A)
B)
C)
D)
2.
A)
B)
C)
D)
What is the hybridization of the oxygen atom in alcohols?
sp
sp
sp2
sp3
1.
OH
C
3. What is the nucleophile in the following substitution reaction?
(CH3)3COH + HBr
(CH3)3CBr + H2O
A)
B)
C)
D)
1) (CH3)3COH
is 1
is 2
is 3
is 4
2) (CH3)3C
3) Br
4) H
4. What are the products of the following reaction?
CH3CH2CH2CH2OH + HBr
A) 1-bromobutane and water
B) 1-bromobutane and hydrogen
C) butane and HOBr
+
hydrogen
D) CH3CH2CH2CH2OBr
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5. Arrange the following alcohols in order of their decreasing reactivity with HBr (most
reactive first).
CH2OH
CH3
OH
HC
3
OH
A)
B)
C)
D)
A
A>B>C
A>C>B
C>A>B
B>C>A
B
C
6. What is the product of the following reaction?
→
A) ClCH2CH2CH2CH2OH
B) ClCH2CH2CH2CH2Cl
C) BrCH2CH2CH2CH2Cl
D) ClCH2CH2CH2CH2SOCl
BrCH2CH2CH2CH2OH
+
SOCl2
7. Which of the following undergoes a substitution reaction with sodium cyanide in
DMSO at the fastest rate?
A) CH3CH2F
B) CH3CH2Cl
C) CH3CH2Br
D) CH3CH2I
8. The rate law for the following reaction is:
DMSO
CH3CH2CH2Cl + NaCN
A) rate = k[CH3CH2CH2Cl]
B) rate = k[CH3CH2CH2Cl][NaCN]
C) rate = k[CH3CH2CH2Cl][NaCN]2
D) rate = k[CH3CH2CH2Cl]2[NaCN]
9.
A)
B)
C)
D)
Which of the following reacts the fastest by the SN2 mechanism?
CH3Br
CH3CH2Br
(CH3)2CHBr
(CH3)3CBr
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10. Which halide ion reacts the fastest with cyclopentyl p-toluenesulfonate in
ethanol/water?
OTs
A)
B)
C)
D)
1) Iis 1
is 2
is 3
is 2
2) Br-
3) Cl-
4) F-
11. Which of the following reacts fastest with methanol by the SN1 mechanism?
CH3
1) CH3CH2CH2CH2CH2Br
3) CH3CCH2CH3
Br
2) CH3CH2CHCH2CH3
4) (CH3)3CCH2Br
Br
A)
B)
C)
D)
is 1
is 2
is 3
is 2
12.
A)
B)
C)
D)
A pentacoordinate carbon is a transient species in the _____ mechanism.
SN1
SN2
E1
E2
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13. Which of the following reacts the slowest with sodium cyanide, NaCN?
1)
OTs
2)
A)
B)
C)
D)
OTs
3)
OTs
4)
OTs
is 1
is 2
is 3
is 4
14. Which of the following conditions favor the SN1 mechanism as opposed to the SN2
mechanism?
(A) tertiary alkyl halide
(B) primary alkyl halide
(C) polar solvent
A) only A
B) only B
C) A and C
D) B and C
15. Rank the following in decreasing order of leaving group ability.
O
O
H3C
S
O
CH3CO
Cl
OH
B
C
D
O
A)
B)
C)
D)
A
A>C>D>B
A>C>B>D
C>B>A>D
B>A>C>D
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16. In which of the solvents below would the reaction shown take place at the fastest rate?
CH3CH2CH2CH2CN + NaBr
CH3CH2CH2CH2Br + NaCN
A) ethanol
B) acetic acid
C) dimethyl sulfoxide
D) water
17. Which of the following undergoes SN1 solvolysis in ethanol/water at the fastest rate?
O
OTs
A)
B)
C)
D)
1)
is 1
is 2
is 3
is 4
F
Br
2)
3)
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OCCH3
4)
Answer Key
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
C
D
C
A
B
C
D
B
A
A
C
B
B
C
B
C
A
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