ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
6th Edition
ISBN: 9780072397475
Author: SMITH
Publisher: MCG
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Chapter 5.9, Problem 27P
Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

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When an unknown amine reacts with an unknown acid chloride, an amide with a molecular mass of 163 g/mol (M* = 163 m/z) is formed. In the infrared spectrum, important absorptions appear at 1661, 750 and 690 cm. The 13C NMR and DEPT spectra are provided. Draw the structure of the product as the resonance contributor lacking any formal charges. 13C NMR DEPT 90 200 160 120 80 40 0 200 160 120 80 40 0 DEPT 135 T 200 160 120 80 40 0 Draw the unknown amide. Select Dow Templates More Frage
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