Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 19, Problem 19.65AP
Interpretation Introduction

(a)

Interpretation:

The synthesis of 4methyl3heptanol starting from a compound containing five or fewer carbon is to be stated.

Concept introduction:

Pheromones are natural substances produced and released by animals. They are used by organisms for communicating or signaling. They are also used by insects to mark trails in defense, to show readiness for mating.

Interpretation Introduction

(b)

Interpretation:

The reason as to why the compound 4methyl3heptanol appears to be a mixture of isomers is to be stated.

Concept introduction:

Isomers are the compounds having the same molecular formula but differ in the arrangements of atoms and molecules. The stereoisomer is two or more compounds that differ in the spatial arrangement of the atoms

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(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Y
Dimethyl disulfide, CH,S–SCH3, found in the vaginal secretions of female hamsters, acts as a sexual attractant for the male hamster. Write an equation for its synthesis from methanethiol.
(b) A compound with the molecular formula C4H9CI has four structural isomers. Write the structural formulas for all the four isomers. (c) Arrange the following compounds in order of increasing acidity, and explain the reasons for

Chapter 19 Solutions

Organic Chemistry

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