
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Transcribed Image Text:[o
Consider the reaction scheme below.
Me
Me
of 210
210
COMI20
OH
Hola
Holensal,d bus
9
(ii) Explain briefly the observed regioselectivity.
Iviz gniw
11
toshsvo beiniinoo noitz9
H® (cat.)
With reference to the following reaction scheme:
[monqo 1250 901 ayawis luna no
br
Me
NaBH4, Et₂O
(i) Draw a curved arrow mechanism to explain the transformation of 9 into 10.
of main
Me
101 anoitiba Ho
HO
Me, O
Me
10
100 10 Stone &
arq tot abortom saogo
atowens 1004 Viitzut vford bre
ooort mott gnis2 H)
osogor (1)
Me
Miel Me
12
*
OH
(i) Draw Newman projections for the two lowest energy conformations of ketone 11.
(ii) Considering your answer to part (i), identify which is the most reactive conformation
of 11 and explain your choice.
(iii) Indicate the stereochemistry (at C*) of the major diastereoisomer of alcohol 12. Use
appropriate strereochemical drawings to explain your answer.
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