Connect Online Access 1-Semester for Organic Chemistry
Connect Online Access 1-Semester for Organic Chemistry
6th Edition
ISBN: 9781260475609
Author: SMITH, Janice
Publisher: Mcgraw-hill Higher Education (us)
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Chapter 7.4, Problem 5P
Interpretation Introduction

(a)

Interpretation: The solubility of chondrocole A in water and CH2Cl2 is to be predicted.

Concept introduction: The solubility of solute in solution depends upon the polarity of solute and solvent. The solute and solvent of same polarity are soluble with each other and insoluble if the polarity is different.

Interpretation Introduction

(b)

Interpretation: The stereogenic centers are to be identified and labeled as R or S.

Concept introduction: A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. The groups around the stereogenic center are prioritized on the basis of atomic number of their atoms in order to find the configuration of compound.

Interpretation Introduction

(c)

Interpretation: A stereoisomer and a constitution isomer of chondrocole A is to be drawn.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. Two compounds that have same molecular formula but different structural arrangement of atoms are known as constitutional isomers.

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Chondrocole A is a marine natural product isolated from red seaweed that grows in regions of heavy surf in the Pacic Ocean. (a) Predict the solubility of chondrocole A in water and CH2Cl2. (b) Locate the stereogenic centers and label each as R or S. (c) Draw a stereoisomer and a constitutional isomer of chondrocole A.
(a) Are compounds B–D identical to or an isomer of A? (b) Give theIUPAC name for A.
The cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.

Chapter 7 Solutions

Connect Online Access 1-Semester for Organic Chemistry

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