Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter FRP, Problem 39P

Fluorination of (R)-2-flurobutane yields a mixture of isomers with the formula C 4 H 8 F 2 .

(a) How many diffcrc.nr isomers would you expect to be produced? Write their structures.

(b) If the mixture of C 4 H 8 F 2 isomers were subjected to fractional distillation, how many fractions would you expect to obtain?

(c) Which of these fractions would be optically active?

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Chlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO. (a) What are these two compounds? (b) Write structural formulas for the enol intermediates that lead to each of these compounds. (c) Using curved arrows, show the flow of electrons in the reaction of each of the enols with Cl2.
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A compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.

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Organic Chemistry

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