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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Chapter
Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Although they have similar molecular masses (73 and 74 amu, respectively), the boiling point of 1-butanamine is much lower (78°C) than that of 1-butanol (118°C). Explain why.

Interpretation Introduction

Interpretation:

Reason behind the lower boiling point of 1-butanamine compared to that of 1-butanol having similar molecular mass has to be explained.

Concept Introduction:

Amines are an organic compound that has amino group as its functional group.  Amine has boiling point that is intermediate between the alkane and alcohols.  This is due to the ability of forming intermolecular hydrogen bonding.  Tertiary amines have lower boiling point than primary and secondary amines of similar molecular mass as hydrogen bonding is not possible.

Explanation

Given compounds are 1-butanamine and 1-butanol.  1-butanamine has an amino group as its functional group.  1-butanamine is a primary amine.  The nitrogen atom has a lone pair of electron and two hydrogen atoms attached to it.  These can involve in intermolecular hydrogen bonding.  While considering 1-butanol, it is an alcohol that contains oxygen atom with two lone pair of electrons and a hydrogen atom.  The electronegativity of oxygen atom is more than that of the nitrogen atom...

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