2. For the following nucleophilic substitution reaction: Br + NaOC(CH3)3 CH3 CH3 'CH3 a. Draw the first transition state (TS1), the reaction intermediate, and the second transition state (TS2) in the labeled boxes. Make sure to show any formal charges, unfilled p-orbitals, and correct stereochemistry. TS₁ Intermediate TS2 b. Which of three molecules you drew for part 'a' is lowest in energy? Write your answer in the box below. c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use wedged and dashed lines to clearly show the resulting stereochemistry at each chiral center. If there is more than one possible product, draw one in each box - if not, leave one box blank. CH3 + NaOC(CH3)3 Br

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
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2. For the following nucleophilic substitution reaction:
NaOC(CH3)3
CH3
'CH3
CH3
a. Draw the first transition state (TS1), the reaction intermediate, and the second m
transition state (TS2) in the labeled boxes. Make sure to show any formal charges,
unfilled p-orbitals, and correct stereochemistry.
TS₁
41001
Intermediate
ogmos
TS2
amond-
b. Which of three molecules you drew for part 'a' is lowest in energy? Write your
answer in the box below.
c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use
wedged and dashed lines to clearly show the resulting stereochemistry at each chiral
center. If there is more than one possible product, draw one in each box - if not, leave
one box blank.
CH3
Br
+ NaOC(CH3)3
Transcribed Image Text:2. For the following nucleophilic substitution reaction: NaOC(CH3)3 CH3 'CH3 CH3 a. Draw the first transition state (TS1), the reaction intermediate, and the second m transition state (TS2) in the labeled boxes. Make sure to show any formal charges, unfilled p-orbitals, and correct stereochemistry. TS₁ 41001 Intermediate ogmos TS2 amond- b. Which of three molecules you drew for part 'a' is lowest in energy? Write your answer in the box below. c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use wedged and dashed lines to clearly show the resulting stereochemistry at each chiral center. If there is more than one possible product, draw one in each box - if not, leave one box blank. CH3 Br + NaOC(CH3)3
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