Illumina Ex. 1113
`IPR Petition - USP 10,435,742
`
`

`

`COVER PHOTO: Lithium dilsopropylamlde molecular graphic produced by
`SYBYUMENDYL Molecular Modeling Software, courtesy of Tripos Associates,
`Inc., st. Louis, MO.
`
`CHAPTER OPENING PHOTO CREOBTS
`Chapter 17 Martin Rotker/Phototake.
`Chapter 1 Dennis Kunkel/Phototake.
`Chapter 18 Dennis Kunkel/Phototake.
`Chapter 2 Michael Siegel/Phototake.
`Chapters 19 & 20 Dr. E. R. Degginger.
`Chapter 3 Dr. E. R. Degglnger.
`Chapter 21 Dennis Kunkel/Phototake.
`Chapters 4-10 Manfred Kage/
`Chapter 22 Phillip A. Harrington/
`Peter Arnold, Inc.
`Peter Arnold, Inc.
`Chapters 11 & 12 Dr. E. R. Degginger.
`Chapter 23 w. C. Still, Columbia
`Chapter 13 Manfred Kage/Peter
`University
`Arnold, Inc.
`Chapter 24 David Gnlzak/Phototake.
`Chapter 14 Dr. E. R. Degginger.
`Chapters 15 & 16 Manfred Kage/
`Peter Arnold, Inc.
`
`Production supervisor: Elizabeth A. Austin
`Cover & Interior designer: Dawn L. Stanley
`Illustrations: John Balballs with the assistance of the Wiley Illustration Department
`Photo editor: Safra Nimrod
`Manuscript editor: Jeannette Stiefel under the supervision of Deborah Herbert
`
`Copyright© 1976, 1980, 1984 & 1988, by John Wiley & Sons, Inc.
`
`All rights reserved. Published simultaneously in Canada.
`
`Reproduction or translation of any part of
`this work beyond that permitted by Sections
`107 and 108 of the 1976 United States Copyright
`Act without the permission of the copyright
`owner is unlawful. Requests for permission
`or further information should be addressed to
`the Permissions Depaf\illent, John Wiley & Sons.
`
`Library of Co11gress Catalogi11g i11 Publicatio11 Data:
`
`Solomons, T. W. Graham.
`Organic chemistry.
`
`Bibliography: p. B-1
`Includes index.
`1. Chemistry, Organic.
`QD251.2.S66
`1988
`ISBN 0-4 71-83659-1
`
`I. Title.
`547
`
`87-29443
`
`Printed in the United States of America
`10 9 8 7 6 5 4 3 2 1
`
`

`

`Alkenes and Alkynes I.
`Properties and Synthesis
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`

`

`254 ALKENES AND ALKYNES I. PROPERTIES AND SYNTHESIS
`
`location of the double bond by using the number of the first atom of the double
`bond as a prefix:
`
`I
`2
`3
`4
`CH 2=CHCH 2CH 3
`1-Butene
`(not 3-butene)
`
`CH 3CH=CHCH 2CH 2CH 3
`2-Hexene
`(11ot 4-hexene)
`
`3. Indicate the locations of the substituent groups by the numbers of the carbon
`atoms to which they are attached.
`
`CH 3
`I
`CH 3C=CHCH 3
`2
`I
`3
`4
`2-Methyl-'2-butene
`(not 3-methyl-2-butene)
`
`CH 3
`CH 3
`I
`I
`CH 3C=CHCH2CHCH 3
`2
`5
`I
`3
`4
`6
`2,5-Dimethyl-2-hexene
`(not 2,5-dimethyl-4-hexene)
`
`CH 3
`I
`CH 3CH=CHCH 2C-CH 3
`15 6
`I
`2
`3
`4
`CH 3
`5,5-Dimethyl-2-hexene
`
`4
`3
`2
`I
`CH 3CH=CHCH2Cl
`
`1-Chlorn-2-butene
`
`4. Number substituted cycloalkenes in the way that gives the carbon atoms of the
`double bond the 1- and 2- positions and that also gives the substituent groups the
`lower numbers at the first point of difference. With substituted cycloalkenes it is
`not necessary to specify the position of the double bond since it will always be
`on C-1. The two examples listed here illustrate the application of these rules.
`
`CH 3
`
`:6:·· .. •
`
`1-Methykyclopentene
`(not 2-methykyclopentene)
`
`1 0
`
`CH 3
`
`H3C
`4
`3,5-Dimethylcyclohexene
`( not 4,6-dimethylcyclohexene)
`
`5. Two frequently encountered alkenyl groups are the vinyl group and the ally!
`group.
`
`H
`"'
`
`/
`H
`
`/
`C=C
`
`H
`. "
`
`H
`
`"'
`
`/
`H
`
`/
`C=C
`
`H
`"
`
`CH 2 -
`
`or
`CH 2=CH(cid:173)
`The vinyl group
`
`or
`CH 2=CHCH 2 -
`The allyl group
`
`l
`
`

`

`6.2 NOMENCLATURE OF ALKENES AND CYCLOALKENES 255
`
`The following examples illustrate how these names are employed:
`
`"'
`
`H
`
`"'
`
`/
`C=C
`
`H
`
`/
`Br
`H
`Bromoethene
`01"
`vinyl bromide
`(common)
`
`H
`
`"'
`
`/
`C=C
`
`H
`
`"'
`
`/
`CH 2Cl
`H
`3-Chloropropene
`01"
`aUyl chloride
`(common)
`
`6. Designate the geometry of a double bond with two identical groups with the
`prefixes cis- and trans-. If two identical groups (usually hydrogen atoms) are on
`the same side of the double bond, it is cis; if they are on opposite sides, it is trans.
`
`CH3
`
`"'
`
`/
`C=C
`
`H
`
`"'
`
`/
`H
`
`CH2CH 3
`trans-2-Pentene
`
`In the next section we shall see another method for designating the geometry of
`the double bond.
`
`PROBLEM 06.2
`
`w:l~{t:mul:~or;>iil~;t¥f ~j~~t}~C>\
`
`: •. (c) 3-£thylcyclohexehe
`(cl) 'vinylcy~l6he:ican{!
`<(e)'.4;4-Dirnethy1:17heielle
`
`(11) (,2,:l?i11.1eihylcycl9hf~en~,
`/ ,{i) 1j:bi~ethylcyclopent~ne
`' '°<ff 1;s:.nibromocyclohe~e~~:
`
`-·:- -: '-.':, ·_,~ ,'v\--'·
`
`,
`
`