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CHEM 2312: Homework 3
Due before class on Wednesday, February 25, 2015. Please provide all your answer within the given
space, and turn in a scantron sheet for the multiple choice questions.
Multiple Choice (48 points, please copy your answers to a SCANTRON card):
1. What is the IUPAC name for the following compound?
O
NO 2
H
O2N
a. 3-Methyl-5-(2,5-dinitrobenzyl)pentanal
b. 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal
c. 3-Methyl-5-(2,5-dinitrophenyl)pentanal
d. 3-Methyl-5-(2,5-dinitrophenyl)butylaldehyde
e. 3-Methyl-5-(2,5-dinitrophenyl)valeraldehyde
2. Which of the reagents listed below would efficiently accomplish the transformation of 3-methyl-3-cyclopentenone into 3-methyl-3-cyclopentenol?
+
a. 1) LiAlH4; 2) H3O
+
b. 1) NaBH4; 2) H3O
c. H2, Pd-C, EtOH
d. (a) and (b)
e. (a), (b), and (c)
3. Which of the following is not a synthesis of benzophenone (diphenylketone)?
O
a.
OH
1. SOCl2
2. AlCl3,
benzene
CN
b.
OH
c.
2. H 3O+
H 3CO
PCC
1. PhMgBr
OCH3
HCl
d.
CH2Cl2
H 2O
e. All of these will yield benzophenone
4. Which of the reagents listed below would efficiently accomplish the transformation of 4-hydroxybutanal to
succinic acid?
a. KMnO4, NaOH
b. Na2Cr2O7, H2SO4
c. Ag2O, NaOH, H2O
d. (a) and (b)
e. (a), (b), and (c)
5. What would be the final product P?
Ph 3P
CH 3I
C6H 5Li
PhCOCH 3
P
Et 2O
OH
a.
b.
d.
e.
c.
6. What product would result from the following reaction?
O
1. DIBAL-H
(excess)
O
O
O
O
a.
b.
O
2. H 2O
OH
c.
O
OH
OHC
HO
d.
e.
O
OHC
HO
7. What would be the final product M?
O
OCH3
TsOH
O
a.
OH
HO
1. LiAlH 4
HCl
1. CH 3MgBr
(excess)
2. H 2O
H 2O
2. H 2O
M
OH
b.
O
OCH3
OH
c.
O
O
O
OH
OH
O
d.
e.
O
O
8. The Baeyer-Villiger oxidation of cyclopentyl methyl ketone produces chiefly:
O
O
a.
O
O
b.
O
O
c.
OH
O
O
d.
O
+
H
O
e.
9. What would you expect to be the major product C of the following sequence of reactions?
COOH
SOCl2
A
B
heat
1. LiAlH(OtBu) 3
C
2. H 2O
O
OH
a.
b.
O
H
OtBu
c.
O
d.
H
e.
OH
10. Which of the reagents listed below would serve as a simple chemical test to distinguish between
benzylalcohol and benzaldehyde?
a. PCC, CH2Cl2
b. AgNO3, NH3
c. Na2Cr2O7, H2SO4
d. KMnO4, NaOH, heat
e. more than one of these
11. Which of the following is not a synthesis of acetophenone?
OH
a.
N
aq. HCl
KMnO 4, NaOH
b.
heat
1. O3
c.
2. Zn, HOAc
HgSO 4
d.
H 2O
e. All of these will give acetophenone
12. Which of these reactions will not produce a 1° alcohol?
O
a.
CHO
1. DIBAL-H
b.
OCH3
2. H 2O
2. H 2O
c.
Br
e. more than one of these
1. Mg, Et 2O
2. ethyleneoxide
3. H 2O
1. NaBH 4
d.
COOH
1. LiAlH 4
2. H 2O
13. (20 points) For each of the following reactions, fill in the missing reagent, product, or starting material.
Note: Each transformation can be carried out in a single step.
a)
O
1. PhMgBr
H
2. H 2O
b)
O
OH
H 3CO
H
O
O
c)
1. BuLi
2. PhCHO
O
O
d)
N
aq. HCl
e)
OH O
CHO
Cl
O
Cl
14. (16 points) Provide a detailed (stepwise) mechanism for each of the following conversions. Draw
curved arrows on the left side of each reaction to account for the formation of the structures on the right
(Note: each arrow symbolizes the movement of 2 electrons).
a)
NH 2
NH 2
O
+
O
H+
N
EtOH
N
b)
H 3O+
HO
O
OH
H 2O
OHC
CHO
Multistep Syntheses (16 points):
Provide a sequence of reactions (show only reagents and synthetic intermediates) to perform each of the
following transformations:
a)
O
b)
OH
COOH
COOH