Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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In addition to organic halides, alkyl tosylates react with organocuprates (R2CuLi) to form coupling products R–R′. When 2° alkyl tosylates are used as starting materials (R2CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi.
Draw the structure of all products of the
mechanism below.
H:I:SH
1:54
H₂N—C—C—C=c
CH3
H
H
H
+ enantiomer
OB
LCH₂
CH3
O A
O C
Identify the major organic product generated from the reaction shown.
(Note: D = a deuterium atom, which behaves just like an H atom)
OD
A
CH3
D
'D
+ enantiomer
B
D₂
Pd
?
CH3
H
+ enantiomer
D
CH3
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