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Chapter 11: Q51P (page 589)

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a)1 equivalent of NaH, followed by 1 equivalent of CH3l and heat

(b)2 equivalents of NaH, followed by 2 equivalents of CH3l and heat

(c) 3 equivalents of NaH, followed by 3 equivalents of CH3l and heat

Short Answer

Expert verified

The compounds that are used to synthesize the methyl-substituted organic compound are called methylating agents. Some of the examples are diazomethane, iodomethane, dimethyl sulfate, etc,

Step by step solution

01

About methylating agents

The compounds that are used to synthesize the methyl-substituted organic compound are called methylating agents. Some of the examples are diazomethane, iodomethane, dimethyl sulfate, etc,

02

About sodium hydride

The combustible base that is used in the synthesis of organic compounds is sodium hydride (NaH). This compound is comprised of sodium ions and one proton in a 1:1 ratio.

03

(a) Reaction of the given compound with 1 equivalent of NaH, followed by 1 equivalent CH3l of and heat

The COOH group of the given compound gets converted to group in this reaction. It is shown below.

Reaction of the given compound with 1 equivalent of NaH, followed by 1 equivalent of CH3l and heat

04

(b) Reaction of the given compound with 2 equivalent of NaH, followed by 2 equivalent of CH3l and heat

The COOH group of the given compound gets converted to COOCH3 and one OH group gets converted to OCH3group in this reaction. It is shown below.

Reaction of the given compound with 2 equivalent of NaH, followed by 2 equivalent of CH3l and heat

05

(c) Reaction of the given compound with 3 equivalent of NaH, followed by 3 equivalent of CH3l and heat

The COOH group of the given compound gets converted to COOCH3and two OH group gets converted to OCH3group in this reaction. It is shown below.

Reaction of the given compound with 3 equivalent of NaH, followed by 3 equivalent of CH3l and heat

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