3. Stereochemistry. Give the structure of the major product formed for each of the following reactions. Provide an explanation for your choice of stereochemistry. OTMS a. 1. BnO дома 160 °C (sealed tube) b. Me -Me 2. HF, CH3CN, rt 3. PDC, 4 Å mol. sieves, CH2Cl2 180 °C B toluene (sealed tube) 70% a. LIN(TMS)2, TMSCI LOSEM THF,-100 °C b. warm to rt C c. 5% aq HCI workup 71% Et SEM CH2CH2SiMe3 A 97%

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter8: Addition Via Carbocation
Section: Chapter Questions
Problem 6CTQ
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Stereochemistry. Give the structure of the major product formed for each of the following reactions. Provide an explanation for your choice of
160 C(sealedtube)
2.HF,CH3CN.n
stereochemistry. a.
->
A 97% HF, CH, CN, rt PDC, 4A mol. sieves, CH2Cl2 A97% ic. a. LiN(TMS), TMSCI THF
, -100°C b. warm to rt c. 5% aq HCl workup C 71%
3. Stereochemistry. Give the structure of the major product formed for each of the
following reactions. Provide an explanation for your choice of stereochemistry.
a.
1.
OTMS
BnO
CO₂Me
160 °C (sealed tube)
Me
b.
-Me
2. HF, CH3CN, rt
3. PDC, 4 Å mol. sieves, CH2Cl2
180 °C
B
toluene
(sealed tube)
70%
C.
a. LiN(TMS)2, TMSCI
LOSEM
THF,-100 °C
b. warm to rt
с
c. 5% aq HCI workup
71%
Et
SEM CH2CH2SiMe3
A
97%
Transcribed Image Text:Stereochemistry. Give the structure of the major product formed for each of the following reactions. Provide an explanation for your choice of 160 C(sealedtube) 2.HF,CH3CN.n stereochemistry. a. -> A 97% HF, CH, CN, rt PDC, 4A mol. sieves, CH2Cl2 A97% ic. a. LiN(TMS), TMSCI THF , -100°C b. warm to rt c. 5% aq HCl workup C 71% 3. Stereochemistry. Give the structure of the major product formed for each of the following reactions. Provide an explanation for your choice of stereochemistry. a. 1. OTMS BnO CO₂Me 160 °C (sealed tube) Me b. -Me 2. HF, CH3CN, rt 3. PDC, 4 Å mol. sieves, CH2Cl2 180 °C B toluene (sealed tube) 70% C. a. LiN(TMS)2, TMSCI LOSEM THF,-100 °C b. warm to rt с c. 5% aq HCI workup 71% Et SEM CH2CH2SiMe3 A 97%
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