Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 22, Problem 22.38P
Interpretation Introduction

(a)

Interpretation: The acceptable names for the given compounds are to be predicted.

Concept introduction: IUPAC nomenclature is a systematic way of naming the organic compounds. The basic principles of IUPAC naming for hydrocarbon are:

• The hydrocarbon is named after the longest carbon chain.

• The parent hydrocarbon containing ester group is named with suffix “ate”.

• The alkyl group bonded to oxygen through single bond forms the first part of the ester and alkyl group bonded to carbonyl group forms the second part.

Expert Solution
Check Mark

Answer to Problem 22.38P

The acceptable name of the compound A is 2-methylpropyl 2, 2-dimethylpropanoate and compound B is 2-ethylhexanenitrile.

Explanation of Solution

The given compound A is,

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  1

Figure 1

The red coloured ball has two bonds. So, this is the oxygen atom. The black coloured atoms have four single bonds. So, these are the carbon atoms. The grey coloured balls have one bond. So, these are the hydrogen atoms. The molecular structure of the compound is,

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  2

Figure 2

This compound contains ester group. The alkyl group attached to carbonyl group has longest chain of three carbon atoms with two methyl groups substituted at the second carbon atom. The alkyl group bonded to oxygen through single bond has longest chain of three carbon atoms with one methyl group substituted at the second carbon atom. The acceptable name of the compound is 2-methylpropyl 2, 2-dimethylpropanoate.

The given compound B is,

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  3

Figure 3

The blue coloured ball has three bonds. So, this is the nitrogen atom. The black coloured atoms have four bonds. So, these are the carbon atoms. The grey coloured balls have one bond. So, these are the hydrogen atoms. The molecular structure of the compound is,

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  4

Figure 4

The given compound B contains longest chain of six carbon atoms with ethyl group substituted at the second carbon atom. The acceptable name of the compound is 2-ethylhexanenitrile.

Conclusion

The acceptable name of the compound A is 2-methylpropyl 2, 2-dimethylpropanoate and compound B is 2-ethylhexanenitrile.

Interpretation Introduction

(b)

Interpretation: The products formed on treatment of A or B with given reagents: [1] H3O+; [2] OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O is to be predicted.

Concept introduction: The metal hydride reagents are good reducing agents such as LiAlH4. They can be used to reduce carbonyl compounds, conjugated double bonds, amides or triple bonds and the CX bond in alkyl halides and epoxides.

When the esters and nitriles are hydrolyzed to carboxylic acids in acidic medium and in basic medium carboxylate ions are formed.

Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases.

Expert Solution
Check Mark

Answer to Problem 22.38P

The reaction of compound A with given reagents are shown below.

[1] H3O+

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  5

Figure 5

 [2] OH, H2O

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  6

Figure 6

 [3] CH3CH2CH2MgBr (excess) then H2O

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  7

Figure 7

 [4] LiAlH4, then H2O.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  8

Figure 8

The reaction of compound B with given reagents are shown below.

[1] H3O+

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  9

Figure 9

 [2] OH, H2O

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  10

Figure 10

 [3] CH3CH2CH2MgBr (excess) then H2O

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  11

Figure 11

[4] LiAlH4, then H2O.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  12

Figure 12

Explanation of Solution

The reaction of compound A with given reagents are shown below.

[1] H3O+

The ester group undergoes acidic hydrolysis to form alcohol and carboxylic acid as shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  13

Figure 13

The products formed are 2, 2-dimethylpropanoic acid and 2-methylpropanol.

[2] OH, H2O

The ester group undergoes basic hydrolysis to form alcohol and carboxylic acid as shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  14

Figure 14

The products formed are 2, 2-dimethylpropanoate ion and 2-methylpropanol.

[3] CH3CH2CH2MgBr (excess) then H2O.

The given ester compound reacts with excess Grignard reagent followed by hydrolysis to form 4-tert-butylheptan-4-ol. The corresponding reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  15

Figure 15

The product formed is form 4-tert-butylheptan-4-ol.

[4] LiAlH4, then H2O.

In presence of lithium aluminium hydride, the ester group is reduced to two alcohols. The corresponding reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  16

Figure 16

The products formed are 2, 2-dimethylpropanol and 2-methylpropanol.

The reaction of compound B with given reagents are shown below.

[1] H3O+

The cyano group undergoes acidic hydrolysis to form carboxylic acid as shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  17

Figure 17

The products formed is 2-ethylhexanoic acid

[2] OH, H2O

The cyano group undergoes basic hydrolysis to form carboxylate ion as shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  18

Figure 18

The product formed is 2-ethylhexanoate ion.

[3] CH3CH2CH2MgBr (excess) then H2O

The nitrile compound reacts with Grignard reagent to form alcohol. The corresponding reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  19

Figure 19

[4] LiAlH4, then H2O.

In the presence of lithium aluminium hydride, the ester group is reduced to two alcohols. The corresponding reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 22, Problem 22.38P , additional homework tip  20

Figure 20

The product formed is 2-ethylhexanamine.

Conclusion

The products formed on treatment of A or B with given reagents: [1] H3O+; [2] OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O is shown in Figure 13-20.

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Chapter 22 Solutions

Organic Chemistry-Package(Custom)

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