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Chapter 22: Problem 532

Synthesize n-pentylamine from any alcohol using the process of (a) Hofmann degradation (b) nitrile reduction (c) reductive amination

Short Answer

Expert verified
To synthesize n-pentylamine (\(C_{5}H_{11}N\)) using the given processes, perform the following steps: (a) Hofmann degradation: 1. Convert n-hexanol (\(C_{6}H_{13}OH\)) to n-hexylamine using hydrochloric acid. 2. Perform Hofmann degradation by reacting n-hexylamine with hypobromous acid and aqueous sodium hydroxide to obtain n-pentylamine. (b) Nitrile reduction: 1. Convert pentyl alcohol (\(C_{5}H_{11}OH\)) to pentanenitrile via pentyl chloride, using thionyl chloride and potassium cyanide. 2. Reduce pentanenitrile to n-pentylamine using lithium aluminum hydride. (c) Reductive amination: 1. Convert pentyl alcohol to pentanal with pyridinium chlorochromate (PCC). 2. Perform reductive amination by reacting pentanal with ammonium chloride and sodium cyanoborohydride to form n-pentylamine.

Step by step solution

01

Convert n-hexanol to n-hexylamine

To do this, react n-hexanol with hydrochloric acid to form n-hexyl chloride: \[C_{6}H_{13}OH + HCl \rightarrow C_{6}H_{13}Cl + H_{2}O\]
02

Convert n-hexylamine to n-pentylamine using Hofmann degradation

React n-hexylamine with hypobromous acid (HOBr) and aqueous sodium hydroxide (NaOH) to yield n-pentylamine: \[C_{6}H_{13}NH_{2} + 2NaOH + Br_{2} \rightarrow C_{5}H_{11}NH_{2} + 2NaBr + H_{2}O\] (b) Nitrile reduction: To synthesize n-pentylamine using nitrile reduction, we can start with pentyl alcohol (\(C_{5}H_{11}OH\)).
03

Convert pentyl alcohol to pentanenitrile

First, react pentyl alcohol with thionyl chloride (SOCl₂) to form pentyl chloride, and then react with potassium cyanide (KCN) to form pentanenitrile: \[C_{5}H_{11}OH + SOCl_{2} \rightarrow C_{5}H_{11}Cl + SO_{2} + HCl\] \[C_{5}H_{11}Cl + KCN \rightarrow C_{5}H_{11}CN + KCl\]
04

Reduction of nitrile to amine

Reduce pentanenitrile to n-pentylamine using lithium aluminum hydride (LiAlH₄): \[C_{5}H_{11}CN + 4LiAlH_{4} \rightarrow C_{5}H_{11}NH_{2} + 4LiAlH_{3}\] (c) Reductive amination: In this process, we will use pentanal (\(C_{5}H_{10}O\)) which can be synthesized from pentyl alcohol.
05

Convert pentyl alcohol to pentanal

First, react pentyl alcohol with pyridinium chlorochromate (PCC) to form pentanal: \[C_{5}H_{11}OH + PCC \rightarrow C_{5}H_{10}O + \text{reduced PCC}\]
06

Reductive amination of pentanal

React pentanal with ammonium chloride (\(NH_{4}Cl\)) and sodium cyanoborohydride (\(NaBH_{3}CN\)) to form n-pentylamine: \[C_{5}H_{10}O + NH_{4}Cl + NaBH_{3}CN \rightarrow C_{5}H_{11}NH_{2} + NaCl + H_{2}O\]

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Most popular questions from this chapter

Show how the following transformations might be achieved with the aid of azide derivatives. (a) \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{OH} \rightarrow \mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\)

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Show how the following compounds might be prepared from the commercially available nitroalkanes obtained from the nitration of propane. (a) \(\mathrm{CH}_{2}=\mathrm{CHNO}_{2}\) (c) \(\mathrm{HOCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}_{2}\) (b) \(\left(\mathrm{O}_{2} \mathrm{NOCH}_{2}\right)_{3} \mathrm{CNO}_{2}\) (d) \(\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}_{2}\)

What is a good method (an easy method that gives a pure product in good yield) for carrying out the following transformation? $$ \mathrm{R}-\mathrm{CH}_{2}-\mathrm{Br} \rightarrow \mathrm{R}-\mathrm{CH}_{2}-\mathrm{NH}_{2} $$

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