,Solutions manual to accompany
Organic
Chemistry
Second Edition
Jonathan Clayden, Nick Greeves, and Stuart Warren
Jonathan Clayden
University of Manchester
Stuart Warren
University of Cambridge
1
, 1
Great Clarendon Street, Oxford, OX2 6DP,
United Kingdom
Oxford University Press is a department of the University of Oxford.
It furthers the University’s objective of excellence in research, scholarship,
and education by publishing worldwide. Oxford is a registered trade mark of
Oxford University Press in the UK and in certain other countries
© Oxford University Press 2013
The moral rights of the authors have been asserted
First edition published 2001
Impression: 1
All rights reserved. No part of this publication may be reproduced, stored in
a retrieval system, or transmitted, in any form or by any means, without the
prior permission in writing of Oxford University Press, or as expressly permitted
by law, by licence or under terms agreed with the appropriate reprographics
rights organization. Enquiries concerning reproduction outside the scope of the
above should be sent to the Rights Department, Oxford University Press, at the
address above
You must not circulate this work in any other form
and you must impose this same condition on any acquirer
British Library Cataloguing in Publication Data
Data available
978–0–19–966334–7
Printed in Great Britain by
Ashford Colour Press Ltd, Gosport, Hampshire
Links to third party websites are provided by Oxford in good faith and
for information only. Oxford disclaims any responsibility for the materials
contained in any third party website referenced in this work.
,
Suggested solutions for Chapter 2 2
PROB LE M 1
Draw good diagrams of saturated hydrocarbons with seven carbon atoms
having (a) linear, (b) branched, and (c) cyclic structures. Draw molecules based
on each framework having both ketone and carboxylic acid functional groups
in the same molecule.
Purpose of the problem
To get you drawing simple structures realistically and to steer you away
from rules and names towards more creative and helpful ways of
representing molecules.
Suggested solution
There is only one linear hydrocarbon but there are many branched and
cyclic options. We offer some possibilities, but you may have thought of
others.
linear saturated hydrocarbon (n-heptane)
some branched hydrocarbons
some cyclic hydrocarbons
We give you a few examples of keto-carboxylic acids based on these
structures. A ketone has to have a carbonyl group not at the end of a chain; a
carboxylic acid functional group by contrast has to be at the end of a chain.
You will notice that no carboxylic acid based on the first three cyclic
structures is possible without adding another carbon atom.
Organic
Chemistry
Second Edition
Jonathan Clayden, Nick Greeves, and Stuart Warren
Jonathan Clayden
University of Manchester
Stuart Warren
University of Cambridge
1
, 1
Great Clarendon Street, Oxford, OX2 6DP,
United Kingdom
Oxford University Press is a department of the University of Oxford.
It furthers the University’s objective of excellence in research, scholarship,
and education by publishing worldwide. Oxford is a registered trade mark of
Oxford University Press in the UK and in certain other countries
© Oxford University Press 2013
The moral rights of the authors have been asserted
First edition published 2001
Impression: 1
All rights reserved. No part of this publication may be reproduced, stored in
a retrieval system, or transmitted, in any form or by any means, without the
prior permission in writing of Oxford University Press, or as expressly permitted
by law, by licence or under terms agreed with the appropriate reprographics
rights organization. Enquiries concerning reproduction outside the scope of the
above should be sent to the Rights Department, Oxford University Press, at the
address above
You must not circulate this work in any other form
and you must impose this same condition on any acquirer
British Library Cataloguing in Publication Data
Data available
978–0–19–966334–7
Printed in Great Britain by
Ashford Colour Press Ltd, Gosport, Hampshire
Links to third party websites are provided by Oxford in good faith and
for information only. Oxford disclaims any responsibility for the materials
contained in any third party website referenced in this work.
,
Suggested solutions for Chapter 2 2
PROB LE M 1
Draw good diagrams of saturated hydrocarbons with seven carbon atoms
having (a) linear, (b) branched, and (c) cyclic structures. Draw molecules based
on each framework having both ketone and carboxylic acid functional groups
in the same molecule.
Purpose of the problem
To get you drawing simple structures realistically and to steer you away
from rules and names towards more creative and helpful ways of
representing molecules.
Suggested solution
There is only one linear hydrocarbon but there are many branched and
cyclic options. We offer some possibilities, but you may have thought of
others.
linear saturated hydrocarbon (n-heptane)
some branched hydrocarbons
some cyclic hydrocarbons
We give you a few examples of keto-carboxylic acids based on these
structures. A ketone has to have a carbonyl group not at the end of a chain; a
carboxylic acid functional group by contrast has to be at the end of a chain.
You will notice that no carboxylic acid based on the first three cyclic
structures is possible without adding another carbon atom.
