Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 7, Problem 27P
Interpretation Introduction

Interpretation:

The 3d formulas of the given compounds is to be written and name using EZ configuration or RS configuration for the isomers of given compounds is to be given.

Concept introduction:

The molecules that are nonsuperimposable or not identical with their mirror images are known as chiral molecules.

A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active.

The stereoisomers that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers.

The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

EZ configuration is used to designate alkene diastereomers (cis-trans isomers).

First, give priority according to Cahn-Ingold-Prelog convention rules:

The higher the atomic mass, the higher will be the priority.

If priority cannot be assigned according to atomic mass, then assign the priority according to first point of difference.

If both the priority groups are on same side of the double-bonded carbon atom, then it is known as (Z) configuration.

But if both the priority groups are diagonal to each other, then it is (E) configuration.

Configuration is used to differentiate between enantiomers.

After giving priority to four groups, rotate the molecule such that the fourth priority group is at the horizontal position.

Now, move from 1-2-3; if it is in clockwise, then it is (R) configuration and if it is in anticlockwise direction, then it is (S) configuration.

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Give the structure, exclusive of stereochemistry, of the principal organic product formed on reaction of 2,3-dimethyl-1,3-butadiene with each of the following:(a) 2 mol H2, platinum catalyst(b) 1 mol HCl (product of 1,2-addition)(c) 1 mol HCl (product of 1,4-addition)(d) 1 mol Br2 (product of 1,2-addition)(e) 1 mol Br2 (product of 1,4-addition)(f) 2 mol Br2
(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation.  (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active.  (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C.  (iii) Name the product formed when compound A undergoes bromination reaction.

Chapter 7 Solutions

Organic Chemistry

Ch. 7 - Practice Problem 7.11 (a) When...Ch. 7 - Practice Problem 7.14 Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15 Rank the following alcohols...Ch. 7 - Practice Problem 7.16 Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 16PPCh. 7 - Prob. 17PPCh. 7 - Practice Problem 7.20 Show how you might...Ch. 7 - Prob. 19PPCh. 7 - Prob. 20PPCh. 7 - Practice Problem 7.23 Write the structure of...Ch. 7 - Prob. 22PPCh. 7 - Prob. 23PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 26PCh. 7 - Prob. 27PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 29PCh. 7 - Prob. 30PCh. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 34PCh. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 41PCh. 7 - Prob. 42PCh. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 52PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 54PCh. 7 - Prob. 55PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGPCh. 7 - Prob. 5LGPCh. 7 - 7.1 Which conditions/reagents would you employ to...Ch. 7 - Which of the following names is incorrect? (a)...Ch. 7 - 7.3 Select the major product of the reaction Ch. 7 - 7.4 Supply the missing reagents. Ch. 7 - Arrange the following alkenes in order of...Ch. 7 - 7.6 Complete the following synthesis.
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