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 10, Problem 32P

Synthesize each of die following compounds by routes that involve allylic or benzylic brominacion by NBS and any other synthetic steps necessary. Begin by writing a retrosynthetic analysis.

(a)

Chapter 10, Problem 32P, Synthesize each of die following compounds by routes that involve allylic or benzylic brominacion by , example  1

(b)

Chapter 10, Problem 32P, Synthesize each of die following compounds by routes that involve allylic or benzylic brominacion by , example  2

(c)

Chapter 10, Problem 32P, Synthesize each of die following compounds by routes that involve allylic or benzylic brominacion by , example  3

(d)

Chapter 10, Problem 32P, Synthesize each of die following compounds by routes that involve allylic or benzylic brominacion by , example  4

(e)

Chapter 10, Problem 32P, Synthesize each of die following compounds by routes that involve allylic or benzylic brominacion by , example  5

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Each of the following can be prepared by an intramolecular aldol condensation of a diketone. Apply retrosynthetic analysis to deduce the structure of the diketone in each case.
Guiding your reasoning by retrosynthetic analysis, show how you could prepare each of the following compounds from the given starting material and any necessary organic or inorganic reagents. All require more than one synthetic step. (a) Cyclopentyl iodide from cyclopentane (b) 1-Bromo-2-methylpropane from 2-bromo-2-methylpropane (c) meso-2,3-Dibromobutane from 2-butyne (d) 1-Heptene from 1-bromopentane (e) cis-2-Hexene from 1,2-dibromopentane (f) Butyl methyl ether (CH3CH2CH2CH2OCH3) from 1-butene
Propose a reasonable synthesis for each of the following compounds from the indicated starting materials and any other reagents.
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