Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 8, Problem 29P

a.

Interpretation Introduction

Interpretation:The structure of trans -1,2-cyclohexanediol should be drawn in the chair form where both hydroxy groups are at equatorial.

Concept introduction: In cyclohexane, all the six carbons are sp3 hybridized so, the expected angle for the connected atoms will be 109.5o . The most stable conformation of cyclohexane will be the one in which the ring or angle strain is negligible and thus, making the conformation stable. In chair conformation, all the atoms are positioned in the ring in such a way that they adopt this positioning and does not experience any angle or ring strain.

b.

Interpretation Introduction

Interpretation:The flipping of chair during the transformation of trans -1,2-cyclohexanediol to corresponding disilyl ether on reacting with chlorosilane needs to be explained by structural models.

Concept introduction:In cyclohexane, all the six carbons are sp3 hybridized so, the expected angle for the connected atoms will be 109.5o . The most stable conformation of cyclohexane will be the one in which the ring or angle strain is negligible and thus, making the conformation stable. In chair conformation, all the atoms are positioned in the ring in such a way that they adopt this positioning and does not experience any angle or ring strain.

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Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) 3-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanol
Propose a structural formula for the product(s) when each of the following alkenes is treated with H2O/H,SO4. Why are two products formed in part (b), but only one in parts (a) and (c)? (a) 1-Hexene gives one alcohol with a molecular for- mula of C,H140. (b) 2-Hexene gives two alcohols, each with a molecu- lar formula of C,H140. (c) 3-Hexene gives one alcohol with a molecular for- mula of C6H140.
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