Chemistry 211
Chapter 16 quiz #2
1.
Name: _____________________________
The IUPAC name of the following epoxide is:
H3C
H
O
H
1)
2)
3)
4)
2.
CH2CH3
cis-2-ethyl-3-methyloxirane
trans-2-ethyl-3-methyloxirane
trans-1ethyl-2-methyloxycyclopropane
trans-1-ethyl-2-methylethane epoxide
Consider the three compounds below.
A. CH3CH2OCH2CH3
B. CH3CH2CH2CH2CH3
C. CH3CH2CH2CH2OH
The two most similar in boiling point are ____________ and the two most
similar in solubility in water are ________.
1)
3)
3.
2)
4)
A and C, B and C
B and C, A and B
A and B, A and C
A and C, A and C
The role of 18-crown-6 in the reaction shown below is to:
CH3CH2CH2CH2Br + KF
18-crown-6
C6H6, heat
CH3CH2CH2CH2F + KBr
O
O
O
O
18-crown-6
O
O
1)
2)
3)
4)
complex F- by ion-dipole attraction and make it more nucleophilic.
remove Br- by ion-dipole attraction and shift the equilibrium to the
products.
complex K+ by ion-dipole attraction increasing the solubility of KF
and the nucleophilicity of F-.
stabilize the carbocation in the substitution reaction.
Page 1
Chemistry 211
Chapter 16 quiz #2
4.
Name: _____________________________
What is the product of the following reaction?
HBr (xs)
O
Br
Br
1)
3)
O
OH
Br
2)
OH
4)
Br
1)
5.
1
Br
2
2)
3)
3
4)
4
4)
4
What is the major product of the following reaction?
CH3
NBS, benzoyl peroxide
CCl4, heat
NaOCH2CH3
CH3CH2OH
Br
CH2Br
CH2OCH2CH3
CH2OCH2CH3
CH3
Br
1)
2)
3)
OCH2CH3
Br
1)
1
2)
4)
OCH2CH3
3)
2
Page 2
OCH2CH3
3
Chemistry 211
Chapter 16 quiz #2
6.
Name: _____________________________
Which one of the following reactions makes the cyclic ether shown
below?
O
OH
2) HO
OH H2SO4
NaOH
3) HO
4)
1)
7.
H2O, H2SO4
Br
1
2
2)
3)
3
4)
4
How many constitutionally isomeric ethers are there with a formula of
C4H10O?
1)
8.
NaOH
1) HO
only one
two
2)
3)
three
4)
four
Which of the following is compound X of the synthesis shown below?
CH3CH2CH=CH2
Br2/H2O
compound X
NaOH
H2O
O
CH3CH2CH CH2
Br
Br
1) CH3CH2CH
CH2
3) CH3CH2CH
OH
OH
OBr
OH
2) CH3CH2CH
CH2
4) CH3CH2CH
1
2)
CH2
OH
Br
1)
CH
3)
2
Page 3
3
4)
4
Chemistry 211
Chapter 16 quiz #2
9.
Name: _____________________________
What is the product of the following sequence of reactions?
H3C
H
H
1)
O
H3C
10.
H2O
CH3
OH
H3C
3) CH3CH2CCH3 + enantiomer
+ enantiomer
H
Br
H
H
1)
NaOH
CH3
H
2)
Br2/H2O
O
1
Br
Br
4)
CH3
O
H3C
2
2)
CH3
3
3)
4)
4
What is the final product of the following sequence of reactions?
(CH3)2CHOH
PBr3
Mg
1)
diethyl ether
O
2) H3O
1) (CH3)2CHOCH2CH2OH
PCC
+
CH2Cl2
3) (CH3)2CHCH2CHO
O
2) (CH3)2CHCCH3
1)
11.
1
2)
4) (CH3)2CHCH2CO2H
2
3)
3
4)
4
4)
4
What is the product of the reactions below?
CH3CH2CH=CH2
CH3CO3H
1) CH3CH2CHCH2OCH3
CH3OH, H2SO4(cat.)
3) CH3CH2CHCH2OH
OH
OH
2) CH3CH2CHCH2OH
4) CH3CH2CHCH2OH
OCH3
1)
1
CH3
2)
2
3)
Page 4
3
Chemistry 211
Chapter 16 quiz #2
12.
What reagents and/or reaction sequence below would convert cis-3-hexene
to meso-3,4-hexanediol?
1)
2)
3)
4)
13.
Name: _____________________________
OsO4, (CH3)3COOH, (CH3)3COH, NaOH
B2H6/diglyme followed by H2O2/NaOH
O3 followed by Zn/H2O
CH3CO3H followed by NaOH/H2O
Which reagent(s) below converts cyclohexene to trans-1,2cyclohexanediol?
1)
OsO4, (CH3)3COOH, (CH3)3COH,
NaOH
3)
O
2)
O3 followed by Zn/H2O
4)
HIO4
CH3COOH followed by NaOH/H2O
14.
Which of the following is the preferred conformation for epoxide ring
formation? (assume a base is provided)
OH
1)
OH
2)
OH
3)
4)
OH
Br
Br
Br
1)
1
2)
3)
2
Page 5
Br
3
4)
4
Chemistry 211
Chapter 16 quiz #2
15.
Name: _____________________________
Which synthetic pathway below gives a racemic mixture of the following
deuterated compound with little or no isomeric impurities?
H
D
+ enantiomer
OH
H
O
1) cyclopentene
CH3COOH
1) LiAlD4
2) H2O
2) cyclopentene
3) cyclopentene
4) cyclopentene
1)
1
1) BD3/THF
2) H2O2, NaOH
D2/Pt
DCl
2)
Br2, hv
NaOH
CCl4
H2O
H2O, CH3OH
heat
2
3)
Page 6
3
4)
4
No. in No. on
Q-Bank Test
16
2
1
16
4
2
16
6
3
16
8
4
16 10
5
16 12
6
16 14
7
16 16
8
16 18
9
16 20 10
16 22 11
16 24 12
16 26 13
16 28 14
16 30 15
Answer Key for Test "211c16q2.tst", 2/23/2004
Correct Answer
2
2
3
3
1
2
3
2
1
3
2
1
3
2
1
Page 1