Q1 This question has two parts Part A and Part B. Part 1: Acetone can react with a base to give the enolate ion A, which can further react with another acetone molecule to give B. Upon quenching with water, B generates C, the final product of this reaction. :Base H20 C H3C A H. H. H3C H. Acetone a) Draw the structure of A, B, and C b) Using curly arrows, draw the mechanism of the reaction between A and acetone to give compound B. What's the name of this reaction. - c) Draw the two resonance forms (A and D) of the enolate (A) generated by the deprotonation of the a-carbon on acetone and show the interconversion between the two using curly arrows: :Base H3C° H H Acetone

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Q1 This question has two parts Part A and Part B.
Part 1: Acetone can react with a base to give the enolate ion A, which can further react with another
acetone molecule to give B. Upon quenching with water, B generates C, the final product of this
reaction.
:Base
H20
A
H3C
H.
H3C
H.
Acetone
a) Draw the structure of A, B, and C
b) Using curly arrows, draw the mechanism of the reaction between A and acetone to give
compound B. What's the name of this reaction. -
c) Draw the two resonance forms (A and D) of the enolate (A) generated by the deprotonation
of the a-carbon on acetone and show the interconversion between the two using curly
arrows: I
Base
H3C
H
A
D
H
Acetone
d) Knowing that the pka of the a-proton on acetone is 19, choose amongst the following bases
those who will be able to remove the proton, given the pKa of their corresponding
conjugated acids.
H3C-C-H
H H
:Base
H-Base
+
conjugate acid
pka = 19
pКa 3 а, b, с, d
a) Ammonia; pKa = 9.2
b) Sodium amide; pka = 38
c) Sodium ethoxide; pka = 16
d) Butyl lithium; pKa = 50
ExamOnline Exam Template
Part 2:
Fill in the following scheme with the appropriate reagents, intermediates and/or products. ,
' What kind of reaction is the first step of the synthetic pathway that converts benzyl chloride
into benzaldehyde (A)?
он
Step 1
A
benzyl chloride
Base
cyclopentanone
Transcribed Image Text:Q1 This question has two parts Part A and Part B. Part 1: Acetone can react with a base to give the enolate ion A, which can further react with another acetone molecule to give B. Upon quenching with water, B generates C, the final product of this reaction. :Base H20 A H3C H. H3C H. Acetone a) Draw the structure of A, B, and C b) Using curly arrows, draw the mechanism of the reaction between A and acetone to give compound B. What's the name of this reaction. - c) Draw the two resonance forms (A and D) of the enolate (A) generated by the deprotonation of the a-carbon on acetone and show the interconversion between the two using curly arrows: I Base H3C H A D H Acetone d) Knowing that the pka of the a-proton on acetone is 19, choose amongst the following bases those who will be able to remove the proton, given the pKa of their corresponding conjugated acids. H3C-C-H H H :Base H-Base + conjugate acid pka = 19 pКa 3 а, b, с, d a) Ammonia; pKa = 9.2 b) Sodium amide; pka = 38 c) Sodium ethoxide; pka = 16 d) Butyl lithium; pKa = 50 ExamOnline Exam Template Part 2: Fill in the following scheme with the appropriate reagents, intermediates and/or products. , ' What kind of reaction is the first step of the synthetic pathway that converts benzyl chloride into benzaldehyde (A)? он Step 1 A benzyl chloride Base cyclopentanone
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