2. The following questions relate to the synthesis of cecropia juvenile hormone (this hormone plays an important role in insect development), which is shown below. MeCOCH,CO,Et, NaH CO,Me Br 2 CO,Et HO- then H+, heat Moo-P OMe RCO3H MeO .CO,Me 5 NaH cecropia juvenile hormone 4 a. Suggest reagents to convert 1 into 2 in two steps. b. Provide a reaction mechanism to explain how 2 is converted into 3. c. Now thinking backwards from the TM (cecropia juvenile hormone), give the structure of compound 5. d. Is the reaction from 5 to the TM regioselective? Explain your answer.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.60P
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2. The following questions relate to the synthesis of cecropia juvenile hormone (this
hormone plays an important role in insect development), which is shown below.
MECOCH,CO,Et,
NaH
CO,Me
Br
CO,Et
HO- then
H+, heat
Meo-
OMe
RCO3H
МеО
CO,Me
NaH
cecropia juvenile hormone
a. Suggest reagents to convert 1 into 2 in two steps.
b. Provide a reaction mechanism to explain how 2 is converted into 3.
Now thinking backwards from the TM (cecropia juvenile hormone), give the
structure of compound 5.
d. Is the reaction from 5 to the TM regioselective? Explain your answer.
с.
Transcribed Image Text:2. The following questions relate to the synthesis of cecropia juvenile hormone (this hormone plays an important role in insect development), which is shown below. MECOCH,CO,Et, NaH CO,Me Br CO,Et HO- then H+, heat Meo- OMe RCO3H МеО CO,Me NaH cecropia juvenile hormone a. Suggest reagents to convert 1 into 2 in two steps. b. Provide a reaction mechanism to explain how 2 is converted into 3. Now thinking backwards from the TM (cecropia juvenile hormone), give the structure of compound 5. d. Is the reaction from 5 to the TM regioselective? Explain your answer. с.
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