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Chapter 9: Problem 16

Treatment of 1-aminoadamantane, \(\mathrm{C}_{10} \mathrm{H}_{17} \mathrm{~N}\), with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, \(R_{3} N\), involves two successive \(S_{N} 2\) reactions and gives compound \(A\). Propose a structural formula for compound \(A\). COC(=O)C(Br)CCBr 1-Aminoadamantane Methyl A

Short Answer

Expert verified
Based on the step-by-step solution, the structural formula for compound A, resulting from two successive \(S_{N}2\) reactions between 1-aminoadamantane and methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, can be written as: [CH3:4][C@@H:5]([NH2:3][C1:8]12[C@@H](C(C1)(C2))[C3:7]12)[C:2]([CH3:6])(C(C1)(C2))[C3:9]12.

Step by step solution

01

Identify the starting reagents and the mechanism

The starting reagents are 1-aminoadamantane and methyl 2,4-dibromobutanoate, which undergo two successive \(S_{N}2\) reactions. The \(S_{N}2\) mechanism involves a nucleophile attacking the substrate and displacing a leaving group.
02

Identify the nucleophile and electrophilic site in the first reaction

In the first reaction, 1-aminoadamantane acts as the nucleophile, as it possesses a lone pair on the nitrogen atom. The electrophilic site is one of the bromine atoms present on methyl 2,4-dibromobutanoate since bromine is a good leaving group in \(S_{N}2\) reactions.
03

Perform the first \(S_{N}2\) reaction

The nitrogen atom in 1-aminoadamantane attacks one of the electrophilic sites, displacing the bromine atom. The result is a new carbon-nitrogen bond between 1-aminoadamantane and methyl 2,4-dibromobutanoate. One bromine atom is still attached to the butanoate chain. Let's call this intermediate compound B, which still needs to undergo another \(S_{N}2\) reaction.
04

Identify the nucleophile and electrophilic site in the second reaction

In the second reaction, the same nitrogen in intermediate compound B, now with a formal positive charge, once more acts as a nucleophile. The electrophilic site is the remaining bromine atom on the butanoate chain.
05

Perform the second \(S_{N}2\) reaction

The nitrogen atom in intermediate compound B attacks the electrophilic site, displacing the bromine atom. The result is a new carbon-nitrogen bond, creating a five-membered ring in compound A.
06

Propose the structural formula for compound A

Based on the successive \(S_{N}2\) reactions that have occurred, the structural formula for compound A can be written as: [CH3:4][C@@H:5]([NH2:3][C1:8]12[C@@H](C(C1)(C2))[C3:7]12)[C:2]([CH3:6])(C(C1)(C2))[C3:9]12-Cds.tight

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Most popular questions from this chapter

Draw a structural formula for the product of each \(\mathrm{S}_{\mathrm{N}} 2\) reaction. Where configuration of the starting material is given, show the configuration of the product.

Attempts to prepare optically active iodides by nucleophilic displacement on optically active bromides using I \(\mathrm{I}^{-}\)normally produce racemic iodoalkanes. Why are the product iodoalkanes racemic?

Treatment of the following stereoisomer of 1-bromo-1,2-diphenylpropane with sodium ethoxide in ethanol gives a single stereoisomer of 1,2 -diphenylpropene. Predict whether the product has the \(E\) configuration or the \(Z\) configuration.

Account for the relative rates of solvolysis of these compounds in aqueous acetic acid.

Elimination of HBr from 2-bromonorbornane gives only 2-norbornene and no 1-norbornene. How do you account for the regioselectivity of this dehydrohalogenation? In answering this question, you will find it helpful to look at molecular models of both 1-norbornene and 2-norbornene and to analyze the strain in each.
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