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 2LGP
Interpretation Introduction

Interpretation:

The given reaction using mechanistic arguments involving Newman projections is to be explained.

Concept Introduction:

▸ Newman projected two types of spatial arrangements of molecules: staggered and eclipsed Newman projections.

▸ Staggered conformation: It is the arrangement of atoms or groups of atoms in a molecule resulting in a 60 dihedral angle. It is also called anti-coplanar transition or anti-conformation. It has low potential energy because of less torsional strain and hence, is more stable

▸ Eclipsed conformation: It is the arrangement of atoms or groups of atoms in a molecule resulting in a 0 dihedral angle. It is also called syn-planar transition or gauche-conformation. It has high potential energy because of high torsional strain and hence, is less stable.

▸ The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules.

▸ A pair of two mirror images which are non-identical is known as enantiomers which are optically active.

▸ The objects or molecules which are superimposable with their mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry.

▸ 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.

▸ The stereoisomers which are non-superimposable on each other and not mirror images of each other are known as diastereomers.

▸ Chiral molecules are capable of rotating plane polarized light

▸ The molecules which are superimposable or identical with their mirror images are known as achiral molecules, and achiral molecules are not capable of rotating the plane-polarised light.

▸ Priority is given to all the four group attached to the chirality center.

▸ Priority is assigned on the basis of the atomic number of the atom. Higher the atomic number, higher will be its priority.

▸ If priority cannot be assigned according to atomic mass, then, it is assigned according to first point of difference.

▸ After assigning priority to the four groups, rotate the molecule such that fourth priority group is away from the observer.

▸ Now, move from a to b to c; if the direction is clockwise, then the chiral center designated as (R) and if the direction is anticlockwise, then the chiral center designated as (S).

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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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