For the following pairs 6f favorable and explain the basis of your prediction. (a) Which isomer will solvolyze more rapidly in acetic acid? OSO,Ph or OSO,Ph

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter25: Biomolecules: Carbohydrates
Section25.SE: Something Extra
Problem 51AP
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for a
faicr thdil
CH,OH
ch of the
For the following pairs of reactions, indicate which you would expect to be more
favorable and explain the basis of your prediction.
(a) Which isomer will solvolyze more rapidly in acetic acid?
OSO, Ph
or
OSO,Ph
ernative
(b) Which will be the major reaction product?
CH
CH
CH,
CH
KOCCH)
or
CH,CCCH,CH,Br
CH
CH
CH
Which isomer will be converted to a quarternary salt more rapidly?
NICH)
NICH
or (CHC
(CH)C
Transcribed Image Text:for a faicr thdil CH,OH ch of the For the following pairs of reactions, indicate which you would expect to be more favorable and explain the basis of your prediction. (a) Which isomer will solvolyze more rapidly in acetic acid? OSO, Ph or OSO,Ph ernative (b) Which will be the major reaction product? CH CH CH, CH KOCCH) or CH,CCCH,CH,Br CH CH CH Which isomer will be converted to a quarternary salt more rapidly? NICH) NICH or (CHC (CH)C
D-mannose
D-chromose A
L-vancosamine
6. Explain the basis for the selective formation of the product shown over the alternative
product.
(a)
CH2
CO,CH3
HO
CH3O,CCCH,CH,CH,OH
not
CH2
0.
(b) H3C.
CH3
H&C
CH;
H3C
CH3
RCO;H
versus
(88%)
(12%)
HB
HC
(c)
preferred to
+ BH;
H3C-N
CH3
CH3
CH3
Transcribed Image Text:D-mannose D-chromose A L-vancosamine 6. Explain the basis for the selective formation of the product shown over the alternative product. (a) CH2 CO,CH3 HO CH3O,CCCH,CH,CH,OH not CH2 0. (b) H3C. CH3 H&C CH; H3C CH3 RCO;H versus (88%) (12%) HB HC (c) preferred to + BH; H3C-N CH3 CH3 CH3
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