Consider the reaction scheme below. Me Me- 0 1970 butto Holament 9 COMI20 OH (ii) Explain briefly the observed regioselectivity. ivile garwol 11 Sa With reference to the following reaction scheme: [monqo lead out ayawin lon an Me HⓇ (cat.) (i) Draw a curved arrow mechanism to explain the transformation of 9 into 10. Totement oni 1011 Me Me, NaBH4, Et₂O Me HO 10 Tot abortom seogool ens Tuo viileu fond bre ont mort guma2 mmH Me 12 Me 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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Chapter1: Chemical Foundations
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[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.
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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