Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 6, Problem 31P
Interpretation Introduction

Interpretation:

The rate of racemization of 2-iodooctane by sodium iodide in acetone is to be compared with the rate of incorporation of radioactive iodine into 2-iodooctane by satisfying the given conditions for each act of exchange.

Concept introduction:

The conversion of optically pure molecule into the mixture of enantiomers (i.e. racemic mixture) is called racemization.

The change in absolute configuration at the chirality center in the substitution reaction is called inversion of configuration.

If the absolute configuration at the chirality center remains same in the substitution reaction, it is called retention of configuration.

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Compound D, shown below, reacts with hydrogen bromide by electrophilic addition. A mixture of two organic compounds, E and F, is formed. CH3 CH₂CH₂ CH3 H compound D HBr Mixture of organic compounds E and F (i) Name the the two organic compounds E and F and show their condensed formula. (ii) Briefly explain the mechanism of the reaction between compound D and hydrogen bromide to form either compound E or compound F. (You can list/state the main steps) (iii) Which compound, E or F is the major product?
(a) Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at arate of 0.05 mol>L per second. What would be the rate if 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used?
A solution of pure (S)-2-iodobutane ([a] = +15.90°) in acetone is allowed to react with radioactive iodide, 131I -, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°. (a) What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?
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