Question 1

Which product is formed when ethyl cyanide (propionitrile) undergoes the following sequence: (1) OH$$^-$$, H$$_2O$$; (2) acetone; (3) phthalic acid, AlCl$$_3$$? Consider the mechanisms involved.

Accepted Answer

A substituted phthalic ketone via Friedel-Crafts acylation

Question 2

In the reaction sequence: (1) NaOEt/EtOH; (2) ethyl bromide; (3) H$$_2O/180$^	ext{o}C$$, starting from glutaric anhydride, what is the final product?

Accepted Answer

A substituted pentanoic acid via alkylation and hydrolysis

Question 3

What is the purpose of POCl$$_3 in $$the reaction sequence starting from benzamide, followed by Grignard addition and then NaOEt/EtOH/heat?

Accepted Answer

To convert benzamide to benzonitrile for further Grignard addition

Question 4

When succinic acid is treated with NaOEt/EtOH and then H$$^+$$, what type of reaction occurs?

Accepted Answer

A Claisen condensation followed by hydrolysis

Question 5

Cyclohexanol is subjected to the following sequence: (1) Jones oxidation; (2) CH$$_2N$_2$$; (3) NH(CH$$_3$$)$$_2$$/Δ; (4) LiAlH$$_4$$; (5) H$$_2O$^+. $$What is the final product?

Accepted Answer

Cyclohexylmethanol

Question 6

The sequence: ketone + H$$_2$$NNH$$_2/H$^+$$, then KOH/DMSO, produces which transformation?

Accepted Answer

A Wolff-Kishner reduction to an alkane

Question 7

What is the product when isopropyl cyanide reacts with CH$$_3CH$_2$$MgBr followed by aqueous workup?

Accepted Answer

Isopropyl ethyl ketone and ammonia

Question 8

What is the outcome when butanol is oxidized, then treated with DIBAH and aqueous workup?

Accepted Answer

Butanal

Question 9

Which sequence converts propanoic acid to a primary amine via the following steps: (1) (COCl)$$_2$$; (2) NH$$_3$$; (3) POCl$$_3$$; (4) Grignard; (5) H$$_2O$$; (6) NaCN/EtOH; (7) LiAlH$$_4$$, then H$$_2O$$?

Accepted Answer

Conversion to a nitrile followed by reduction to a primary amine

Question 10

What is the product of the following sequence: (1) NaOEt/EtOH; (2) ethyl bromide; (3) H$$_2O/180$^	ext{o}C$$, starting from a 1,5-diketone?

Accepted Answer

A cyclopentanone derivative

Question 11

Which reaction sequence would produce cyclohexanone from a suitable precursor using NaOEt/EtOH and heat?

Accepted Answer

A Claisen condensation followed by hydrolysis and decarboxylation

Question 12

What is the product of the following sequence: (1) NaCN/H$$^+$$; (2) H$$_2O/$$heat; (3) NaBH$$_4/$$EtOH; (4) H$$^+$$, starting from methyl vinyl ketone?

Accepted Answer

A saturated alcohol

Question 13

Which of the following best describes the mechanism of the Wolff-Kishner reduction?

Accepted Answer

Conversion of a ketone to an alkane via hydrazone intermediate and base-induced elimination

Question 14

In the Claisen condensation, which intermediate is formed after the initial deprotonation of the ester?

Accepted Answer

A carbanion stabilized by resonance with the carbonyl group

Question 15

Which reagent is most suitable for the selective reduction of an ester to an aldehyde?

Accepted Answer

DIBAH

Question 16

What is the main product when a nitrile is treated with a Grignard reagent followed by aqueous workup?

Accepted Answer

A ketone

Question 17

Which step in the malonic ester synthesis is responsible for introducing a new alkyl group?

Accepted Answer

Alkylation with an alkyl halide

Question 18

In the acetoacetic ester synthesis, what is the purpose of heating with aqueous acid after alkylation?

Accepted Answer

To hydrolyze the ester and decarboxylate the intermediate

Question 19

Which of the following is a key feature of the mechanism for the formation of an enolate ion?

Accepted Answer

Deprotonation of the alpha carbon by a base

Step-by-Step Guidance for Organic Chemistry Reactions: Carboxylic Acid Derivatives, Condensations & Alpha Carbon Reactions

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