Study Guide
Chemistry 22 Homework Set 7
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University:
Amherst College -
Course:
CHEM 221 | Organic Chemistry I Academic year:
2023
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Views:
45
Pages:
4
Author:
Kamren Monroe
Chem 22
Homework set 7
End-of-chapter problems from Hornback: Ch 18: (note that I’ve tried to exclude all the problems
that involve reductive amination — that's a little too far off track) 27a-h,j-o,q-s, 28-35, 36a-c,e,h,
37, 38a-c,e-g, 39-42, 43a-f,h-k, 44-47, 49, 52-57.
1. Write mechanisms for the (a) acid- and (b) base-catalyzed hemiacetal formations below.
(a)
H+
O
HO
O
H2O
OH
(b)
OH–
O
HO
O
H2O
OH
2. (a) Write a mechanism for the acid-catalyzed acetal formation below. You may abbreviate
+
+
the proton-transfer steps as "–H " and "+H ", but make sure the sequence is clear and
reasonable. (b) Write the mechanism for the reverse reaction — acetal hydrolysis with acid and
excess water. (c) If the acetal below is treated with methanol and acid, a trans-acetalization
occurs to form 1,1-dimethoxycyclobutane. Write the mechanism of that reaction.
HO
O
OH
O
H+
O
3. Draw the products of the following reactions.
O
O
H+
OH
Ph
OH
H+
O
CH3NH
NH2
H+
N
H+
H2O 4. Write a mechanism for formation of the aminal (that's aminal, not animal) below. You
haven't seen this reaction before, but you can figure it out anyway.
Ph
H
N
N
H
Ph
+
H+
O
Ph
N
N Ph
5. Here's a refresher on reaction stereochemistry. Draw the organic products of the following
reactions, showing stereochemistry as appropriate. Label stereoisomeric products as appropriate.
O
1. Et–MgCl
O
OCH3
NaBH4
2. H+
EtOH
O
OH
1. LiAlH4
CrO3
pyridine
2. H+
O
1. CH3MgI
2. H+
1. LiAlD4
O
2. H+
6. (a) How would you make each alcohol below two different ways, by the addition of a
Grignard reagent to a carbonyl compound? Draw the reactants you would use.
OH
Ph
OD
5-methyl-2-hexanol
Ph
OEt
(b) Two of the three can also be made by reduction of a carbonyl compound. Write those rxns.
7. Suggest a route for these syntheses. You may need to do some reviewin’ of Chem 21 stuff,
but that’s okay ‘cause it’s just a homework problems.
O
(a)
Ph
Phenylacetylene
Ph
(as the only souce of C)
(b) Make 1,2,3-triphenyl-2-propanol starting from toluene as the only source of carbon. Chem 22
Spring 2010
Name _________________________________________
HW set 7
30 points; due Wed, March 24 at the beginning of class.
1. Write the mechanisms of the acid- and base-catalyzed hemiacetal ring openings below. Show
each and every step in all its glory, including every little H+ transfer.
(a)
O
H+
OH
(b)
O
H2O
HO
OH–
OH
H2O
HO
O
O
2. Write the mechanism of the acid-catalyzed hydrolysis of the cyclic imine below, and draw the
+
+
product. You may abbreviate the proton-transfer steps as "–H " and "+H " (you're welcome!),
but make sure the sequence is clear and reasonable.
H+
N
H2O 3. Draw the products of the following reactions, including stereochemistry. Label products to
indicate their stereochemical relationships where appropriate.
(a)
O
O
OH
HO
(1 equiv)
1. Ph–MgCl
H+
2. H+, H2O
(b)
OH
HO
O
Br
H+
1. Mg
2. PhCHO
3. H+, H2O
4. (a) Cyanohydrin formation is reversible. Rank the following compounds according to the
amount of cyanohydrin present at equilibrium (1 = least cyanohydrin; 4 = most).
Benzaldehyde
p-methoxybenzaldehyde
p-nitrobenzaldehyde
p-chlorobenzaldehyde
(b) Draw the cyanohydrin produced
from the most reactive compound
5. Devise a synthesis of the compound below, starting from benzyl alcohol and aniline as the
only sources of aromatic rings.
N
Ph
Ph
Ph
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Chemistry 22 Homework Set 7
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