Question 1

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Direct alkylation of an enolate.

Question 2

LDA is a strong, sterically hindered base and will form the _______enolate. Sodium hydroxide is a weak base and will form the_______ enolate. Kinetic enolates are the_____ stable and thermodynamic enolates are the______ stable.

A) kinetic, thermodynamic, most, least
B) thermodynamic, kinetic, most, least
C) kinetic, thermodynamic, least, most
D) thermodynamic, kinetic, least, most

thermodynamic, kinetic, least, most

Accepted Answer

thermodynamic, kinetic, least, most&#10;

Question 3

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Direct Alkylation of an ester.

Question 4

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Acetoacetic ester synthesis is used to create a ketone.

Question 5

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

To alkylate the terminal carbon of the acetoacetic ester synthesis, you need to use potassium amide or some other strong base.

Question 6

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The Malonic ester synthesis can be used to create acids.

Question 7

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Malonic ester synthesis can also be used to create cyclic compounds.

Question 8

What is the correct order of reagents to achieve the following synthesis? A) 1) KNH₂/NH₃ 2) Butyl chloride 3) Propyl iodide 4) OH^-, H₂O 5) H₃O⁺ 6) heat B) 1) NaOEt/EtOH 2) Butyl chloride 3) Potassium tert-butoxide 4) Propyl iodide 5) OH^-, H₂O 6) H₃O+ C) 1) NaOEt/EtOH 2) Butyl chloride 3) NaOEt/EtOH 4) Propyl iodide 5) OH^-, H₂O 6) H₃O⁺ D) 1) NaOEt/EtOH 2) Potassium tert-butoxide 3) Butyl chloride 4) Propyl iodide 5) OH^-, H₂O 6) H₃O⁺

Accepted Answer

Only b gives the correct order to produce the correct product. A and D try to produce a dianion which will not work. C will not produce the product because sodium ethoxide is not strong enough to deprotonate the substituted carbon between the two esters.

Question 9

What is the product of the following reaction?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Direct alkylation of an active hydrogen compound, a nitrile.

Question 10

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Formation of a Stork enamine, followed by addition of acid chloride.

Deck 18: Reactions at the Α Carbon of Carbonyl Compounds