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Chapter 18: Q35P (page 906)

Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?

Short Answer

Expert verified

Temozolomide is a cancer-fighting drug that can be taken orally. When its present in the circulatory system, it is transformed into its active form by combining with water and losing carbon dioxide.

When it is present inside the cell, it eliminates a methyl diazonium ion.

Step by step solution

01

Temozolomide

Temozolomide is a cancer-fighting drug that can be taken orally. When its present in the circulatory system, it is transformed into its active form by combining with water and losing carbon dioxide.

When it is present inside the cell, it eliminates a methyl diazonium ion.

02

Identifying the amide bond that is hydrolyzed in the first step of the conversion of temozolomide to methyl diazonium

The carbon dioxide molecule is lost immediately after the hydrolysis of the amide bond. The bond indicated below is the amide bond that is hydrolyzed, as carbon dioxide can be lost since the electrons left behind can be delocalized onto the carbonyl oxygen.

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Question: How can you prepare the following compounds with benzene as one of the starting materials?

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What is the product of the following reaction?

Show how the following compounds can be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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