Chapter 21: Enols and Enolates

Question 1

Alpha Halogenation in acidic conditions

Answer 1

[H3O+],

Br2

Question 2

Alpha, beta-unsaturation of a ketone

Answer 2

(1) [H3O+], Br2

(2) pyridine

Question 3

Haloform Reaction

Answer 3

(1) NaOH, Br2

(2) [H3O+]

Question 4

Aldol Reaction

Answer 4

NaOH, H2O

Question 5

Aldol Condensation to form alpha, beta unsaturated ketone

Answer 5

NaOH, H2O, heat

Question 6

Crossed aldol reaction

Answer 6

(1) add Strong Base to carbonyl 1
(2) carbonyl 2
(3) H2O

Question 7

Claisen condensation…

Answer 7

Start with ester…

(1) appropriate base
(2) H3O+

Question 7

Alkylation with enolate: thermo

Answer 7

(1) NaH
High temp

(2) Alkyl halide

Question 7

Alkylation with enolate: kinetic

Answer 7

(1) LDA
Low temp

(2) Alkyl Halide

Question 7

Malonic ester synthesis

Answer 7

To diethylmalonate add

(1) NaOEt
(2) Alkyl halide
(3) H3O+

Question 7

Acetoacetic ester synthesis

Answer 7

To ethyl acetoacetate add

(1) NaOEt
(2) Alkyl halide
(3) H3O+

Question 8

Alkylation with cuprate thing

Answer 8

(1) R2CuLi
(2) Michael Acceptor
(3) H3O+

Question 9

Alkylation twice

Answer 9

(1) R2CuLi

(2) RX

Question 10

Stork Enamine synthesis

Answer 10

(1) R2NH
(2) Michael Acceptor
(3) H3O+

Question 11

Robinson annulation

Answer 11

(1) NaOH + Michael donor

(2) NaOH, heat