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Show how m-toluidine can be converted to the following

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 37SP Chapter 19

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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19
1
Problem 37SP

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

Step-by-Step Solution:

Solution 37SP

Step 1</p>

(a)

Treatment of m-toluidine with sodium nitrite in the presence of strong acid gives 3-methylbenzenediazonium salt. This process is known as diazotization.

Step 2 </p>

Next, 3-methylbenzenediazonium salt is reacted with cuprous cyanide (CuCN) and forms the desired product (3-methylbenzonitrile). This reaction is known as Sandmeyer reaction.

Step 3</p>

(b)

Treatment of m-toluidine with sodium nitrite in the presence of strong acid gives 3-methylbenzenediazonium salt. This process is known as diazotization.

Step 4 </p>

Next, 3-methylbenzenediazonium salt is reacted with cuprous cyanide (CuCN) and forms 3-methylbenzonitrile. This reaction is known as Sandmeyer reaction.

Step 5 </p>

Lithium aluminum hydride () is used as a reducing agent for the conversion of cyanide to amine. So, treatment of 3-methylbenzonitrile with followed by the hydrolysis gives the desired product (m-tolylmethanamine).

Step 6 </p>

(c)

Treatment of m-toluidine with sodium nitrite in the presence of strong acid gives 3-methylbenzenediazonium salt. This process is known as diazotization.

Step 7 </p>

Next, 3-methylbenzenediazonium salt is reacted with potassium iodide (KI) and forms the desired product (1-iodo-3-methylbenzene). This reaction is known as Sandmeyer reaction.

Step 8 of 13

Chapter 19, Problem 37SP is Solved
Step 9 of 13

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Show how m-toluidine can be converted to the following

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