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Chapter 16: Q70P (page 795)

Question: Fill in the boxes with the appropriate reagents:

Short Answer

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Answer

The appropriate reagent of the following given reaction is shown below:

Step by step solution

01

Reaction of Aldehyde with Grignard reagent

The reaction of an aldehyde or a ketone with a Grignard reagent is a nucleophilic addition reaction鈥攖he nucleophilic Grignard reagent adds to the carbonyl carbon then it forms an alkoxide ion that is complexed with the magnesium ion. In the end addition of dilute acid breaks up the complex and we get the desired alcoholic product.

02

Identifying the appropriate reagent

In the given reaction, first reagent used is Grignard reagent in the presence of acid HCl, which undergoes reaction with propanal to form an secondary alcohol, that goes on oxidation with second reagent NaOCl in the presence of acetic acid to form butan-2-one. This butan-2-one undergoes esterification by reagents HCl in the presence of excess alcohol to form an ester as a desired product as shown in the figure given below:

Selection of reagents

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Most popular questions from this chapter

Rank the following compounds from most reactive to least reactive toward nucleophilic addition:

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized.

a.

b.

c.

d.

e.

f.

g.

h.

(show two methods)

i.

(show two methods)

When trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known鈥攊n detective novels, at least鈥攁s a "Mickey Finn." Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.

Propose a mechanism to explain how dimethyl sulfoxide and oxalyl chloride react to form the dimethylchlorosulfonium ion used as the oxidizing agent in the Swern oxidation.

Question: Show two ways to convert an alkyl halide into a carboxylic acid that has one more carbon than the alkyl halide.
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