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Chapter 22: Problem 570

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

Short Answer

Expert verified
To convert pent-2-en-4-ol to pent-2-en-4-amine using azide derivatives, follow these steps: 1. Convert the alcohol group (OH) to an alkyl halide (Cl) using thionyl chloride (SOCl2). 2. Replace the alkyl halide (Cl) with an azide group (N3) using sodium azide (NaN3) in an SN2 reaction. 3. Reduce the azide group (N3) to an amine group (NH2) using either hydrogen gas (H2) with a metal catalyst (Pd-C or Pt) or lithium aluminum hydride (LiAlH4).

Step by step solution

01

Convert the alcohol group to an alkyl halide

To convert the alcohol group (OH) to an alkyl halide, we can use thionyl chloride (SOCl2) as a reagent. This will convert the hydroxyl group (OH) into a chloro group (Cl). Reactant: \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) Reagent: \(\mathrm{SOCl}_{2}\) Product: \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\)
02

Replace the alkyl halide with an azide group

Next, use sodium azide (NaN3) as a nucleophile to replace the chloro group (Cl) with an azide group (N3). This is an SN2 reaction. Reactant: \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) Reagent: \(\mathrm{NaN}_{3}\) Product: \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{N}_{3}\)
03

Reduce the azide group to an amine

For the final step, we will reduce the azide group (N3) to an amine group (NH2) by using either hydrogen gas (H2) with a metal catalyst (such as palladium on carbon or platinum) or using LiAlH\(_{4}\) (lithium aluminum hydride) as the reducing agent. Reactant: \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{N}_{3}\) Reagent (option 1): \(\mathrm{H}_{2} / \mathrm{Pd-C}\) (or \(\mathrm{H}_{2} /\mathrm{Pt}\)) Reagent (option 2): \(\mathrm{LiAlH}_{4}\) Product: \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) Through these three steps, we have successfully converted pent-2-en-4-ol to pent-2-en-4-amine using azide derivatives.

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Most popular questions from this chapter

Reaction of acid chlorides with sodium azide, \(\mathrm{NaN}_{3}\), yields acyl azides, RCON \(_{3}\). When heated, these undergo the Curtius rearrangement to amines, \(\mathrm{RNH}_{2}\), or, in a non-hydroxylie solvent, to isocyanates, RNCO. Using the structure for the azide, suggest a mechanism for the rearrangement.

Discuss the structure, classification, nomenclature and physical properties of amines. Give examples.

At room temperature, the nmr spectrum of 1 -ethylaziridine + CYCLOA shows the triplet-quartet of an ethyl group, and two other signals of equal peak area. When the temperature is raised to \(120^{\circ}\), the latter two signals merge into a single signal. How do you interpret these observations?

Show how a mixture of n-butylamines prepared from n-butyl bromide and an excess of n-butylamine might be resolved into its components by reaction with succinic anhydride, separation of the products through advantage of their solubility properties in acid or base, and regeneration of the corresponding amines. Write equations for the reactions involved.

Arguing on the basis of mechanistic principles and knowledge of related reactions, work out products which might be expected for the following reactions:
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