ORG CHEM CONNECT CARD
ORG CHEM CONNECT CARD
6th Edition
ISBN: 9781264860746
Author: SMITH
Publisher: MCG
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Chapter 13, Problem 34P
Interpretation Introduction

Interpretation: The structures of A-E are to be identified.

Concept introduction: Monochlorination is a radical substitution reaction. In this reaction, Cl replaces hydrogen atom and forms alkyl halide.

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Five isomeric alkanes (A–E) having the molecular formula C6H14 are each treated with Cl2 + hv to give alkyl halides having molecular formulaC6H13Cl. A yields five constitutional isomers. B yields four constitutionalisomers. C yields two constitutional isomers. D yields threeconstitutional isomers, two of which possess stereogenic centers. Eyields three constitutional isomers, only one of which possesses astereogenic center. Identify the structures of A–E.
Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.
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