Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 5, Problem 3PP
Interpretation Introduction

Interpretation:

The new relationships between molecules after modifying the positions of groups is to be examined.

Concept Introduction:

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.

Plane of symmetry is the plane that bisects the molecule in two equal halves, such that they are mirror images of each other.

Compounds having plane of symmetry are usually achiral as they do not have different atoms around the central carbon atom.

The objects which are non-superimposable or not identical with its mirror image are known as chiral objects. The pair of two mirror images which are non-identical are known as enantiomers.

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

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(c) Answer the following questions: It is possible for a compound to be chiral even though it lacks a carbon atom with four different groups. Using two nitro groups, one isopropyl group and one carboxy group as substituents, draw the structure of an optically active biphenyl that is void of a chiral carbon. i. ii. Deduce, giving reasons, whether or not the following molecules are optically active. H3C CH3 ČH(CH3)2 Quaternary ammonium salt NH2 Compound A НОСІНС OCH3 OCH3 Br Compound B
1. (a) A widely prescribed antibiotic (1) is shown below. Copy the structure of this compound into your answer sheet and answer the following questions. HO. (1) (iii) Identify ALL the chiral carbons present in compound (1) by placing an asterisk (*) at the appropriate atoms. (iv) Select ANY ONE of the chiral centres you have identified in part (iii) above and assign the correct Cahn-Ingold-Prelog (R, S) configuration. In your answer include the assignment of priorities.
PRACTICE PROBLEM 2.2 The compounds in each part below have the same (or similar) molecular weights. Which compound in cach part would you expect to have the higher boiling point? Explain your answers. (a) OH or (c) OH or HO (b) (CHN or A factor (in addition to polarity and hydrogen bonding) that affects the melting point of many organic compounds is the compactness and rigidity of their individual molecules. • Molecules that are symmetrical generally have abnormally high melting points. sert- Buryl alcohol, for example, has a much higher melting point than the other isomeric alcohols shown here: OH OH tert-Butyl alcohol (mp 25 "C) Butyl alcohol (mp -00 "C) Isobutyl alcohol sec-Butyl alcohol (mp 108 C) (mp-114 C) о о

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Organic Chemistry

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