1. 2. Identify all four stereoisomers of structure 1. OH tam NH₂ 1 On treatment with nitrous acid (HNO₂) these 4 isomers of 1 react differently. (a) Draw a mechanism for the reaction of each stereoisomer, and hence identify which stereoisomer gives which product A, B or C.

1. 2. Identify all four stereoisomers of structure 1. OH tam NH₂ 1 On treatment with nitrous acid (HNO₂) these 4 isomers of 1 react differently. (a) Draw a mechanism for the reaction of each stereoisomer, and hence identify which stereoisomer gives which product A, B or C.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

1.
2.
Identify all four stereoisomers of structure 1.
OH
to
NH₂
On treatment with nitrous acid (HNO₂) these 4 isomers of 1 react differently.
(a) Draw a mechanism for the reaction of each stereoisomer, and hence identify which stereoisomer
gives which product A, B or C.
(b) Draw the orbital interactions involved in the product-determining step for each reaction.
a to o
A
B

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