Name:_____________________________
GT Student ID:_____________________________
CHEM 2312: Problem Set 2
Due before class on Monday, February 20, 2017. Please provide all your answer within the given
space, and turn in a scantron sheet for the multiple choice questions.
Multiple Choice (48 points):
1. What is the IUPAC name for the following compound?
H
O
Cl
a. 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal
b. 3-Methyl-5-(4-chlorophenyl)-hexanaldehyde
c. 3-Methyl-5-(4-chlorophenyl)hexanol
d. 3-Methyl-5-(4-chlorophenyl)hexanal
e. 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde
2. What is the major product P of the following sequence of reactions?
Cl
AlCl3
O
Cl2, FeCl 3
H 2NNH 2
benzene
P
KOH, heat
O
a.
b.
c.
Cl
Cl
Cl
H 2N
N
O
H 2N
d.
e.
Cl
3. What new compound will eventually be formed when HCl is added to a solution of isobutyraldehyde in
methanol?
a.
OCH3
Cl
b.
O
c.
OH
OH
d.
OCH3
OCH3
OCH3
e.
O
4. Select the reagent(s) for the following reaction:
O
O
OH
O
HO
a. (1) LiAlH4, ether; (2) H2O
+
b. (1) NaBH4; (2) H3O
c. (1) DIBAL, –78°C; (2) H2O
OH
d. (b) and (c)
e. None of the above would be suitable
5. Which of these compounds cannot be reduced with sodium borohydride?
O
O
H
OH
a.
b.
c.
O
d.
O
O
e. more than one of these
6. The Baeyer-Villiger oxidation of methyl phenyl ketone produces chiefly:
O
a.
O
OCH3
O
b.
OCH3 c.
O
O
OH
d.
O
e.
O
7. Which of the following is a suitable synthesis for 2-phenylacetaldehyde?
H
a.
HgSO 4, H 2SO 4
1. DIBAL
b.
CN
2. H 3O+
H 2O
H
1. O3
c.
Na 2Cr2O7
OH
d.
2. Zn, HCl
H 2SO 4
e. None of these would be useful
8. What is the major product Q of the following reaction sequence?
HCN
O
a.
OH
CN
b.
CN
H 2SO 4
LiAlH 4
H 2O
heat
THF
c.
OH
NH 2
H 3O+
Q
d.
e.
OH
OH
COOH
9. What product M would result from the following series of reactions?
OH
SOCl2
O
1. LiAlH(OtBu) 3
1. PhMgBr
2. H 3O+
2. H 2O
OH
a.
M
O
c.
b.
O
OH
d.
e.
10. Which reagent will not differentiate between 3-butenal and 2-butanone?
a. Br2/CCl4
b. Ag2O, NaOH
c. H2NNHC6H5
d. Na2Cr2O7, H2SO4
e. All of these would be suitable
11. How could the following synthesis be accomplished?
OCH3
?
OH
O
O
O
+
a. i) LiAlH4, ii) H3O , iii) PCC
+
b. i) NaBH4, ii) H3O
+
c. i) DIBAL, ii) H3O , iii) PCC
d. i) HOCH2CH2OH, pTsOH, ii) LiAlH4, iii) aq. HCl
e. More than one of these would be suitable
12. What would be the final product K?
PPh 3
Br
PhLi
PhCOCH 3
ether
a.
Ph
Ph
OH
b.
O
Ph
Ph
O
K
c. Ph
Ph
d. Ph
Ph
e. Ph
Ph
Reaction Sequence:
(21 points) Provide structures for reagents and intermediates A - G:
O
A
OH
PBr 3
NaCN
B
C
DMSO
D
O
1. PhMgBr
H
F
E
2. H 2O
Reagent(s) A:
C12H14
Intermediate B:
1. NaBH4
2. H2O
Br
Intermediate C:
Reagent(s) D:
1. DIBAL
+
2. H3O
CN
Intermediate E:
Reagent(s) F:
conc. H2SO4
OH
Product G:
G
Reaction Mechanism (7 points):
Provide a stepwise mechanism for the following reaction. 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).
OH
HO
H+
O
O
O
O
OH
OH
H
OH
O
H
O
O
O
OH
O
O
OH
OH
resonance stabilized
3° carbocation
–H
O
O H
O
OH
+H
O
OH
Multistep Syntheses (24 points):
Provide a sequence of reactions (show reagents and synthetic intermediates) to perform each of the
following transformations. Each transformation can be completed in three steps.
1.
O
OH
1. Step:
OH
PBr 3
Br
Mg, ether
Br
2. Step:
MgBr
CHO
3. H 2O
3. Step:
OH
O
Na 2Cr2O7
H 2SO 4
OH
2.
2.
OH
OCH3
O
O
1. Step:
1. LiAlH 4
OH
OH
2. H 2O
O
2. Step:
PCC
OH
H
CH2Cl2
O
3. Step:
MeO
P
MeO
O
OCH3
O
1. NaH
OCH3
H
2.
O
O