4. Consider the following nucleophilic substitution: CH3 1) CH3O Na* CH3 HO, 2) H* COCH3 A a. Is the reaction Sx1 or SN2? b. Draw the reaction mechanism to show how compound B is formed. c. Label the chiral centre(s) with R/S notation for compound B.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter15: Radical Reactions
Section: Chapter Questions
Problem 14E
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4. Consider the following nucleophilic substitution:
CH3
1) CH3O Na*
CH3
HO.
2) H*
"OCH3
a. Is the reaction Sx1 or SN2?
b. Draw the reaction mechanism to show how compound B is formed.
c. Label the chiral centre(s) with R/S notation for compound B.
d Give TWO uses of acid in this reaction.
e. When acid is added first followed by addition of methanol, compound C, however,
would be the major product of this reaction.
CH3
1) H*
2) CH3ОН
OCH3
CH3
OH
A,
Which one is a stronger nucleophile? CH3ONA* or CH OH? Explain.
ii.
Is the reaction Sxl or SN2?
iii.
Draw the reaction mechanism to show how compound C is formed.
Transcribed Image Text:4. Consider the following nucleophilic substitution: CH3 1) CH3O Na* CH3 HO. 2) H* "OCH3 a. Is the reaction Sx1 or SN2? b. Draw the reaction mechanism to show how compound B is formed. c. Label the chiral centre(s) with R/S notation for compound B. d Give TWO uses of acid in this reaction. e. When acid is added first followed by addition of methanol, compound C, however, would be the major product of this reaction. CH3 1) H* 2) CH3ОН OCH3 CH3 OH A, Which one is a stronger nucleophile? CH3ONA* or CH OH? Explain. ii. Is the reaction Sxl or SN2? iii. Draw the reaction mechanism to show how compound C is formed.
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