4. Treatment of ketone 1 with bromomethyl benzene (PhCH2Br) and a base results in the formation of two different products, A and B, depending on the identity of the base. When lithium diisopropylamide (LDA) is used, product A is formed. When sodium ethoxide (NaOEt) is used, product B is formed. The reaction coordinate diagram for the two reactions is shown below. Ph A 1. Ne Li° CH3 2. Ph NaOH H₂O LDA 1. NaOEt EtOH CH3 2. Ph Br Br B int.B G° AGA int.A AGB Br OH H&C OH B cat. H₂SO A Reaction Coordinate Ph OH Which of the two products is the thermodynamic product for the reaction? Which is the kinetic a. product? heat CHO₂ b. Formation of product B is fairly temperature dependent. Would elevated temperatures or lowered temperatures be expected to promote formation of this product? C. Draw int. A and int. B and rationalize their differences in stability. (hint: this reaction proceeds through a mechanism that is quite similar to the reaction of carbonyl compounds with Br2 in basic conditions)
4. Treatment of ketone 1 with bromomethyl benzene (PhCH2Br) and a base results in the formation of two different products, A and B, depending on the identity of the base. When lithium diisopropylamide (LDA) is used, product A is formed. When sodium ethoxide (NaOEt) is used, product B is formed. The reaction coordinate diagram for the two reactions is shown below. Ph A 1. Ne Li° CH3 2. Ph NaOH H₂O LDA 1. NaOEt EtOH CH3 2. Ph Br Br B int.B G° AGA int.A AGB Br OH H&C OH B cat. H₂SO A Reaction Coordinate Ph OH Which of the two products is the thermodynamic product for the reaction? Which is the kinetic a. product? heat CHO₂ b. Formation of product B is fairly temperature dependent. Would elevated temperatures or lowered temperatures be expected to promote formation of this product? C. Draw int. A and int. B and rationalize their differences in stability. (hint: this reaction proceeds through a mechanism that is quite similar to the reaction of carbonyl compounds with Br2 in basic conditions)
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 29VC
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Transcribed Image Text:4. Treatment of ketone 1 with bromomethyl benzene (PhCH2Br) and a base results in the formation of two different
products, A and B, depending on the identity of the base. When lithium diisopropylamide (LDA) is used, product
A is formed. When sodium ethoxide (NaOEt) is used, product B is formed. The reaction coordinate diagram for
the two reactions is shown below.
Ph
A
1.
Ne
Li°
CH3
2. Ph
NaOH
H₂O
LDA
1. NaOEt
EtOH
CH3
2. Ph
Br
Br
B
int.B
G°
AGA
int.A
AGB
Br OH
H&C
OH
B
cat. H₂SO
A
Reaction Coordinate
Ph
OH
Which of the two products is the thermodynamic product for the reaction? Which is the kinetic
a.
product?
heat
CHO₂
b. Formation of product B is fairly temperature dependent. Would elevated temperatures or lowered
temperatures be expected to promote formation of this product?
C.
Draw int. A and int. B and rationalize their differences in stability. (hint: this reaction proceeds
through a mechanism that is quite similar to the reaction of carbonyl compounds with Br2 in basic
conditions)
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