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 45P
Interpretation Introduction

Interpretation:

The structure of compounds H and I is to be proposed.

Concept Introduction:

Isomers are the molecule that have the same number of atoms but have a different arrangement of the atoms in the space.

Stereoisomers have the same molecular formula, but the arrangement of atoms in the three-dimensional orientation is different.

Enantiomers are the stereoisomers whose molecules have chiral center and are mirrors image to each other.

A pair of two mirror images that are non-identical is known as a pair of enantiomers.

The objects or molecules that are superimposable with their mirror images are achiral objects or molecules. These objects have a centre of symmetry or plane of symmetry.

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

The stereoformula which is depicted in two dimensions, in which stereochemical information is not destroyed, is determined by the Fisher Projection formula.

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.

Alkene react with hydrogen (H2) in the presence of a metal catalyst such as (Ni/Pt) to produce alkane

A chemical reaction between compound and molecular hydrogen in the presence of a catalyst. The addition of hydrogen to double or triple bond is a hydrogenation reaction.

The equimolar mixture of two enantiomers is called a racemic mixture.

Degree of unsaturation of compound can be calculated using expression as:

DU=2C+2+NXH2

Here, C is the number of carbon atoms, N is the number of nitrogen atoms, X is the number of halogen and H is number of hydrogen atoms.

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An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.
Compound A has the formula C9H19Cl. B is a C9H19Br compound.A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products.C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane.Addition of HCl to C yields A as the major product.Propose structures for A and B.
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Chapter 5 Solutions

Organic Chemistry

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