Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Transcribed Image Text:35) Obtain the aromatic derivatives from a multi-step synthesis.
(25 pts)
CI
O A
AICI
NaCN, HCN
E
CI
(i) Me-Cur-Me Lit
(ii)
NaOH, Br2 (XS)
acid workup.
D
MCPBA, CH2Cl2
HO
F
H3O+
CO₂H
Draw the mechanism for Wittig reaction (C-ii):
HO₂C
carboxylic acid
B
(i) NaBH4, MeOH
(ii) H3O+
HO
cyclic ester
(i) Me-CO-CI, FeCl3
(ii) Pr-Br, Ph3P, BuLi
CO₂H
HO₂C
OH
OH
Circle two stereoisomers (racemic) products
Z-alkene
Transcribed Image Text:36) Complete the following multi-step reactions showing applications of enolate ions arising from ketones,
esters, malonic ester, and keto ester, etc.
(30 pts)
(1)
A
NaOH, H₂O+
heat
A
NaOEt
EtO
OEt
(11)
EOH, H+
H.
B
LDA, H₂O+
-78°C
B
(i) NaOMe, Et-Br
(ii) H₂O+, heat
EtOOC
(III)
COOEt
B
A
(i) NaOEt
LiAlH
4-bromo-2-butene
H₂O+
(ii) H3O+, heat
Write the mechanism for Aldol Condensation (I A or B), and Claisen Condensation (II A).
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