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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr
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Predict the major products of the following reactions,

Chapter 3, Problem 41SP

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QUESTION:

Problem 41SP

Predict the major products of the following reactions, including stereochemistry where appropriate.

(a) ( R)-butan-2-ol + TsCl in pyridine

(b) (S)-2-butyl tosylate + NaBr

(c) cyclooctanol + CrO3/H2SO4

(d) cyclopentylmethanol + CrO3 . pyridine. HCl

(e) cyclopentylmethanol + Na2Cr2O7/H2SO4

(f) cyclopentanol + HCl/ZnCl2

(g) n-butanol + HBr

(h) cyclooctylmethanol + CH3CH2MgBr

(i) potassium tert-butoxide + methyl iodide

(j) sodium methoxide + tert-butyl iodide

(k) cyclopentanol + H2SO4/heat

(l) product from (k) + OsO4/H2O2, then HIO4

(m) sodium ethoxide + 1-bromobutane

(n) sodium ethoxide + 2-methyl-2-bromobutane

(o) octan-1-ol + DMSO + oxalyl chloride

(p) 4-cyclopentylhexan-1-ol + DMP reagent

Questions & Answers

QUESTION:

Problem 41SP

Predict the major products of the following reactions, including stereochemistry where appropriate.

(a) ( R)-butan-2-ol + TsCl in pyridine

(b) (S)-2-butyl tosylate + NaBr

(c) cyclooctanol + CrO3/H2SO4

(d) cyclopentylmethanol + CrO3 . pyridine. HCl

(e) cyclopentylmethanol + Na2Cr2O7/H2SO4

(f) cyclopentanol + HCl/ZnCl2

(g) n-butanol + HBr

(h) cyclooctylmethanol + CH3CH2MgBr

(i) potassium tert-butoxide + methyl iodide

(j) sodium methoxide + tert-butyl iodide

(k) cyclopentanol + H2SO4/heat

(l) product from (k) + OsO4/H2O2, then HIO4

(m) sodium ethoxide + 1-bromobutane

(n) sodium ethoxide + 2-methyl-2-bromobutane

(o) octan-1-ol + DMSO + oxalyl chloride

(p) 4-cyclopentylhexan-1-ol + DMP reagent

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