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Chapter 6: Problem 123

Which of the following gives a primary amine on hydrolysis? (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CN}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{NOH}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{NO}_{2}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{NC}\)

Short Answer

Expert verified
a) CH3-CH2-CN b) CH3-CH=NOH c) CH3-CH2-NO2 d) CH3-CH2-NC Answer: Option (c) CH3-CH2-NO2 will produce a primary amine upon hydrolysis.

Step by step solution

01

Understand Primary Amines and Hydrolysis

Primary amines have the general structure \(\mathrm{R-NH_{2}}\), where \(\mathrm{R}\) is any alkyl or aryl group. Hydrolysis is the process where a chemical compound reacts with water, resulting in the breaking of bonds and the formation of new compounds.
02

Analyze Option (a)

The given compound is \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CN}\). During hydrolysis, the nitrile is converted into an amide \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CONH_{2}}\). The amide further undergoes hydrolysis to form \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{COOH}\) and \(\mathrm{NH_{3}}\). However, no primary amine is formed in this process.
03

Analyze Option (b)

The given compound is \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{NOH}\). This is an oxime functional group. Upon hydrolysis, it undergoes a Lossen rearrangement and forms a ketone, which is \(\mathrm{CH}_{3}\mathrm{C(O)}\mathrm{CH}_{3}\) and \(\mathrm{NH_{4}^{+}}\) or water and \(\mathrm{NH_{3}}\), as byproducts. No primary amine is formed in this process.
04

Analyze Option (c)

The given compound is \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{NO}_{2}\). This is a nitro functional group. When it undergoes hydrolysis, it forms a primary amine, \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{NH_{2}}\) and nitric acid, \(\mathrm{HNO}_{3}\). Therefore, option (c) gives a primary amine upon hydrolysis.
05

Analyze Option (d)

The given compound is \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{NC}\). This is an isonitrile functional group, and upon hydrolysis, it forms \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{COOH}\) and \(\mathrm{NH_{3}}\). No primary amine is formed in this process.
06

Conclusion

Based on our analysis, we can conclude that option (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{NO}_{2}\) gives a primary amine upon hydrolysis, making it the correct answer.

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