1. Draw the structure of the aldol self-condensation product for each of the following compounds. If a compound does not undergo aldol self-condensation, explain why it does not. CH;CHCH,CH CH3 а. b. CH3 C. CH3 0 H3C-C-C-H d. CH3
1. Draw the structure of the aldol self-condensation product for each of the following compounds. If a compound does not undergo aldol self-condensation, explain why it does not. CH;CHCH,CH CH3 а. b. CH3 C. CH3 0 H3C-C-C-H d. CH3
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 56AP
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Transcribed Image Text:1.
Draw the structure of the aldol self-condensation product for each of the following compounds. If a
compound does not undergo aldol self-condensation, explain why it does not.
CH;CHCH,CH
CH3
а.
b.
CH3
CH3 0
H;C-Č-C–H
d.
CH3
2.
Consider the reaction below to answer the following question(s):
ini #
H.
+ H20
NaOEt
H.
ELOH
a. Write the complete stepwise mechanism for the reaction above. Show all intermediate structures and
all electron flow with arrows.
b. Refer to Exhibit 23-2. This reaction is an example of:
а.
an intramolecular Claisen condensation
b.
an intramolecular aldol condensation
C.
a Robinson annulation
d.
a Michael reaction
Transcribed Image Text:c. The product of this reaction is:
a 6, y-unsaturated aldehyde
an a, 8-unsaturated ketone
an a, 6-unsaturated aldehyde
an enol
а.
b.
с.
d.
3.
a,B-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the B carbon, as
shown below.
+
:Nu-H
Nu
a. Draw a resonance form for the unsaturated carbonyl that accounts for this reactivity.
b. This reaction is called
reaction.
a 1,2-conjugate addition.
an electrophilic addition.
a direct addition
а.
b.
C.
d.
a 1,2-addition.
4.
Consider the structures below to answer the following question(s).
CH,C-H
OH
H;C
CH
-CH3
II
III
a. Underline the most acidic hydrogens in each of the molecules.
b. Rank the molecules above in order of increasing acidity (least acidic to most acidic).
II, II, I
а.
b. II, III, I
c. I, II, II
d. II, I, II
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