Q: Which of the following is the correct order of reactivity for acid derivatives, from most to least reactive?

$$\text{Acid chloride} \u003e \text{Anhydride} \u003e \text{Ester} \u003e \text{Amide}$$

Question 1

Which of the following best describes a 'disconnection' in retrosynthetic analysis?

Accepted Answer

A process of breaking a molecule into smaller fragments to identify possible synthetic routes.

Question 2

In the retrosynthesis of esters, which of the following disconnections is typically used to yield an electrophilic carbon?

Accepted Answer

C/O disconnection

Question 3

Given the following transformation: $$RCOOH \xrightarrow{$$SOCl_2$$} RCOCl$$, what is the purpose of this reaction in the context of acid derivative synthesis?

Accepted Answer

To convert a carboxylic acid into a more reactive acid chloride for further derivatization.

Question 4

Which of the following is the correct order of reactivity for acid derivatives, from most to least reactive?

Accepted Answer

$$	ext{Acid chloride} \u003e 	ext{Anhydride} \u003e 	ext{Ester} \u003e 	ext{Amide}$$

Question 5

In the synthesis of ethers via the Williamson ether synthesis, which of the following combinations of nucleophile and electrophile is preferred to maximize yield and minimize side reactions?

Accepted Answer

A primary alkoxide ion and a primary alkyl halide

Question 6

Why is over-alkylation a problem in the direct alkylation of amines with alkyl halides?

Accepted Answer

Because the product amine is more nucleophilic and can react further, leading to mixtures of products.

Question 7

Which of the following is a safer and more selective method for synthesizing primary amines from aldehydes or ketones?

Accepted Answer

Reductive amination using $$\ce{NaBH_3CN}$$

Question 8

In the context of two-group C-X disconnections, what is the significance of a 1,3-diX disconnection?

Accepted Answer

It often leads to the identification of a Michael acceptor for conjugate addition.

Question 9

Which functional group is most likely to act as a Michael acceptor in a 1,3-diX disconnection?

Accepted Answer

An $$\alpha,\beta-$$unsaturated carbonyl compound

Question 10

In the synthesis of amines via the azide route, what is a major safety concern?

Accepted Answer

Azides are toxic and potentially explosive.

Question 11

Which of the following best describes the role of functional group interconversion (FGI) in retrosynthetic analysis?

Accepted Answer

FGI is used to convert one functional group into another to enable a desired disconnection.

Question 12

When synthesizing a $$\beta-$$hydroxy ether via a 1,2-diX disconnection, which intermediate is typically involved?

Accepted Answer

An epoxide

Question 13

In the context of nucleophilic substitution reactions, why is NaH often used in ether synthesis?

Accepted Answer

NaH deprotonates alcohols to generate alkoxide ions, which are strong nucleophiles.

Question 14

Which of the following is a key mechanistic consideration when planning a synthesis involving epoxides?

Accepted Answer

Epoxides are attacked at the less hindered carbon by nucleophiles.

Question 15

A retrosynthetic analysis of a molecule reveals a 1,3-dicarbonyl motif. Which synthetic strategy is most appropriate?

Accepted Answer

Michael addition to an $$\alpha,\beta-$$unsaturated carbonyl compound

Question 16

Which of the following statements about the use of cyanide in amine synthesis is correct?

Accepted Answer

Cyanide adds one carbon to the chain and can be reduced to a primary amine.

Question 17

In the context of medicinal chemistry, why is it important to avoid the use of explosive reagents such as acid chlorides with lithium reagents?

Accepted Answer

Safety concerns and the risk of uncontrolled reactions make such routes undesirable.

Question 18

Which of the following is a correct application of a one-group C-X disconnection in the synthesis of an ether?

Accepted Answer

Disconnection to an alcohol and an alkyl halide, followed by Williamson ether synthesis.

Question 19

Which of the following functional group interconversions (FGIs) is necessary before performing a nucleophilic substitution to form an ether from an alcohol?

Accepted Answer

Conversion of the alcohol to an alkyl halide

Medicinal Chemistry: One-Group/Two-Group C-X Disconnections in Organic Synthesis

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