EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 8, Problem 8.28AP
Interpretation Introduction

(a)

Interpretation:

The structures of all alcohols with the molecular formula C5H11OH are to be drawn.

Concept introduction:

The compounds that have the same molecular formula but have different connectivity of molecules are termed as constitutional isomers. The constitutional isomers are also known as structural isomers. These compounds consist of the same chemical formula but the sequence of atoms to each other is different.

Interpretation Introduction

(b)

Interpretation:

The chiral alcohols with the molecular formula C5H11OH are to be identified.

Concept introduction:

A carbon atom that has four non-equivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

Interpretation Introduction

(c)

Interpretation:

All the alcohols with the molecular formula C5H11OH are to be named using IUPAC substitutive nomenclature.

Concept introduction:

The alcohols contain hydroxyl (OH) functional group in their parent chain and are named by adding suffix –ol. The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Interpretation Introduction

(d)

Interpretation:

All the alcohols with the molecular formula C5H11OH are to be classified as a primary, secondary, or tertiary alcohol.

Concept introduction:

On the basis of the position of hydroxyl group in the chain of carbon atoms, alcohols are classified as primary, secondary and tertiary alcohol.

The general formula of primary alcohol is CH2OH.

The general formula of secondary alcohol is CHROH.

The general formula of tertiary alcohol is CR2OH.

Interpretation Introduction

(e)

Interpretation:

In all the alcohols with the molecular formula C5H11OH, the α- carbon on each structure is to be shown.

Concept introduction:

In organic compounds, an alpha carbon atom is the first carbon atom that is bonded to a functional group. In alcohols, the first carbon atom that is bonded to the hydroxyl (OH) functional group is known as the alpha carbon atom, which is denoted as α- carbon in the structure.

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1. (a) Draw the structures of the eight isomeric pentyl alcohols, C3H11OH. (b) Name each by the IUPAC system and by the carbinol system. (c) Label each as primary, secondary, or tertiary, (d) Which one is isopentyl alcohol? tert-Pentyl alcohol? (e) Give the structure of a primary, a secondary, and a tertiary alcohol of the formula C,H13OH.
Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) 3-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanol
Acetyl chloride, CH3COCl, reacts with the hydroxyl groupsof alcohols to form ester groups with the elimination ofHCl. When an unknown compound X with formulaC4H8O3 reacted with acetyl chloride, a new compound Ywith formula C8H12O5 was formed.(a) How many hydroxyl groups were there in X?(b) Assume that X is an aldehyde. Write a possible structure for X and a                 possible structure for Y consistent     with your structure for X.
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