Organic Chemistry, Books a la Carte Edition (9th Edition)

9th Edition

ISBN: 9780134160382

Author: Leroy G. Wade, Jan W. Simek

Publisher: PEARSON

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Textbook Question

Chapter 6, Problem 6.48SP

A solution of pure (S)-2-iodobutane ([α]=+15.90°) in acetone is allowed to react with radioactive iodide, 131|−, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.

a. Determine the percentages of (R)- and (S)-2-iodobutane in the product mixture.
b. What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?

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Chapter 6, Problem 6.47SP

Chapter 6, Problem 6.49SP

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Chapter 6 Solutions

Organic Chemistry, Books a la Carte Edition (9th Edition)

Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4P Ch. 6.4 - Prob. 6.5P Ch. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7P Ch. 6.6B - Prob. 6.8P Ch. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...

Ch. 6.7 - Prob. 6.11P Ch. 6.7 - Prob. 6.12P Ch. 6.8 - Prob. 6.13P Ch. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15P Ch. 6.10A - Prob. 6.16P Ch. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18P Ch. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20P Ch. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23P Ch. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25P Ch. 6.15 - Prob. 6.26P Ch. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28P Ch. 6.16 - Prob. 6.29P Ch. 6 - Prob. 6.30SP Ch. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SP Ch. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SP Ch. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SP Ch. 6 - Prob. 6.38SP Ch. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SP Ch. 6 - Prob. 6.42SP Ch. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SP Ch. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SP Ch. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SP Ch. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SP Ch. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SP Ch. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SP Ch. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SP Ch. 6 - Prob. 6.59SP

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