MORISSON   Organic Chemistry

MORISSON Organic Chemistry


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Transition metal complexes 1042
Stereochemistry of homogeneous hydrogenation:
diastereoselectivity 1046
Stereochemistry of homogeneous hydrogenation:
\u20acnantioselectivity 1049
The oxo process 1052
Enzyme action 1054
29.s
29.6
29.7
29.8
29.9
3A HeterocycHc ConPounds
30.1 Heterocyclic systems 1457
FIVE.MBMBERED RINGS
30.2
30.3
30.4
Structure of pyrrole, furan, and thiophene 1059
Source of pynole, furan, and thiophene 1061
Electrophdic substitution in pyrrole, furan, and thiophene.
Reactivity and orientation 1062
31
CONTENTS
30.5 Saturatedfive-memberedheterocycles 1065
SIX-MEMBERED RINGS
30.6 Structure of pyridine 1066
30.7 Source of pyridine compounds 1067
30.8 Reactions of pyridine 106g
30.9 Electrophilis substitution in pyridine 106g
30.10 Nucleophilic substitution in pyridine 1069
30.1 I Basicity of pyridine t07I
30.12 Reduction of pyridine 1073
Macromolecules. Polymers and polymerization
31.1 Macromolecules 1077
31.2 Polymers and polymerization I07g
31.3 Free-radical vinyl polymerization I0g0
31.4 Copolymerization l0B3
?1.5 Ionic polymerization. Living polymen I0g431.6 Coordination polymerization |OAZ
31,7 Stepreactionpolymerization I0g0
31.8 Structure and properties of macromolecules l0g3
ste_reochemistry- III. Enantiotopii and Diastereotopic Ligands
and Faces
32.1 Introduction I I0l
32.2 Biological oxidation and reduction. Ethanol and
acetaldehyde I ILt
32.3 Biological oxidation and reduction. Deuterium labeling
experiments 1103
3?.4 Biological oxidation and reduction. stereochemistry l I04
125J Enantiotopic and diastereotopic ligands I I0732.6 Enantiotopic and diastereotopic faces I I t0
32.7 Origln ofienantiospecificity I I 12
PART THREE
Biomolecules
33 Lipids Fats s.nd Steroids
33.1 The organic chemistry of biomolecules I I Ig
33.2 Lipids 1120
33.3 Occurrence and composition of fats I I 20
33.4 Hydrolysis of fats. Soap. Micelles I I24
33.5 Fats as souroes of pure acids and alcohols t I2S
33.6 Detergents 1126
33.7 Unsaturated fats. H4rdening of oils. Drying oils II27
33.8 Phosphoglycerides.phosphateesterr. IltS
33.9 Phospholipids and cell membraqes IIJ|
32
CONTENTS
33.10 Biosynthesis of fatty.aoids 1132
33.11 Steroids 1134
34 Carbohydrates I. Monosaccharides
Introduction 1143
Definition and classification
(*)-Glucose: an aldohexose
(-)-Fructose: a 2-ketohexose
Stereoisomers of (*)-glucose.
derivatives 1146
Oxidation. Effect of alkali 1149
Osazone formation. EPimers I 151
Lengthening the carbon chain of aldoses. The Kiliani-Fischer
synthesis I 152
Shortening the carbon chain of aldoses' The Ruff
degradation 1154
Conversion of an aldose into its epimer 1154
Configuration of (*)-glucose. The Fischer proof I155
Configurations ofaldoses 1160
Optical families. o and t- 1162
Tartaric acid 1164
Families of aldoses. Absolute configuration 1166-Cv.ii. 
rir".,"re of o-(*)-glupose. Formation of glucosides 1168
Configuration about C-1 1173
Methylation 1174
Determination of ring size I176
Conformation 1178
34.r
34.2
34.3
34.4
34.5
34.6
34;7
34.8
34.9
34.10
34.1r
34.r2
34.r3
34.14
34.r5
34.16
34.r7
34.18
34.t9
34.20
I 144
I 144
1 146
Nomenclature of aldose
35 carbohydrates II. Disaccharides and Polysaccharides
35.I Disaccharides l18f
35.2 (*)-Maltose 1185
35.3 (*)-Cellobiose 1188
35.4 (*)-Lactose 1j,89
35.5 (*)-Sucrose 1191
35.6 Polysaccharides 1192
35.7 Starch 1193
35.8 Structure of amylose. End group analysis /,193
35.9 Structure of amYloPectin 1195
35.10 CYclodextrins 1198
35.1I Structure of cellulose 1200
35.12 Reactions of cellulose 1200
36 Proteins and Nucleic Acids Molecular Biology
36.1 Proteins 1205
36.2 Structure of amino acids 1206
36.3 Amino acids as dipolar ions 1208
36.4 Isoelectric point of amino acids 1211
36.5
36.6
36.7
36,p
36,9
36.10
35.1 1
36.12
36.t3
36.r4
36.1 5
36.r6
36.17
36.r8
36.t9
36.20
CONTENTS
@Ohfigurationof natural amino acids I2t2
Pireparation of amino acids l2I3
Reactions of amino acids l2ts
Pepqides. Gdometry of the peptide linkage l2Is
Doremrinadon of structure of peptides. Terminal residue
analysls. Partial hydrolysis I2I7
Synthesis ofpeptides 1221
Proteins. Classification and function. Denaturation I22S
Structure of proteins 1226
Peptide chain 1226
Side chains. Isoelectnc poinl Electrophoresis 1227
Conjugated proteins. Prosthetic groups. Coenzymes l22g
Secondary structure ofproteins l22g
Biochemistry, molecular biology, and organic chemistry I2JJ
Mechanism of enzyme action. Chymotrypsin 1236 '
Nucleoprciteins and nucleic acids t24l
Chemistry and heredity. The genetic code 1246
Suggested Readings 12SI
Answers to Problems 1263
Index 1279
Preface
Perhaps the only thing that teachers of organic chemistry today are agreed on
is ttrat ttre textbooks 
-have 
frown too big. And they have - including our own' And
*, *t.fti"f airn in prepaiing this sixth edition was to shorten the book' We havc
;;;; 150 pages iiom it aid, most important, have rewritten the early chaptcn
to -"te ttris funaamental material more accesible to the student.
In shortening the book, however, we have stuck to the principle we hlve
always held: thesi are beginning styde.nts, and they need all the help they can get'
When we take up a topiC we eiplain it as fully and clearly as we can; the book is
shorter simply because we take up iewer topics'
A oo-G, of chapters have disappeared, as chapters. Some of their content
has been moved to otlier chapters. Some has been presented as problems, and is
"-pf"io.A it the Study Guidi; this material is thus available to help students to
Uto"O.o their understanding of organic chemistry beyond the limits of the text-
book. Much has been delrt"i *og"tfter as being less important than new material
that replaces it.---- 
it. systematic treatment of alcohols and ethers has been moved fonn'ard to
Ct apte.O, Jn"re it immediately follows the chapter on alkyl halides. Introduced
"itfri,5 poioq the chemistry of alcohols gives students the opportunity to apply aj.d
buitd onwhat they have just been studying about nucleophilic substitution' They
see Acofrofs x sibstratis, as nucleophiles, and as teavilts q;ou7s' They are intro-
["."Oto the most important-andsimplest-catalytic efect in orpnic chemis"
ti, iiri*ion. (In ihapter 7, alcotrols will appear again, playing still another star
;;-i; ;;;iropttiti. subititution: that of solvent.) With the most important labo-'oto.y 
*utr. of aipn"ti. compounds in their hands, students can begin to carry
out organic synthesis in a realistic way'
Thirty-odd yean ago, when our fint edition appeared, it was a slim volume of
onlyg00p"go.Yet,inouropinion-then,andnow-itpfettJwellpresented
Gi" o"gu-"iichemistry as it was then: a science whose theory had come of age and
*"fO d understoodland enjoyed-by begrnners. The pattern underlying or-
g""i. .ft .irtry had begun to emerge,^ and it was our aim to reveal it to the
i.rO"ott. With the structurat theory before them, it soon became apparent' stu-
xxtv PREFACE
dents could begin to.study organic chemistry, not through rote rnemorization, butthrough/ under s t anding.
But organic chemistry has, of course, continud to grow, and at a tremendous
r4te, Theories have been refined and exceptions to geniralizations found; tniog,
are not so simple as they once seemed. New concepts and new tools have appearei
and established themselves as part of basic organic chemistry: orbital s6;.t.y,for example, or nuclear magnetic resonance. Vtany factors have been found to be
much more important than was previously realized: the role ofthe solvent, stereo-
chemistry in all its aspects, the juxtaposition of reacting grorrpr. Hosts of new
reaBents have been devised: chemoselective, regioselectiieJtereoselective.
with all this grofih, the pattern underlying organic chemistry has becomebroader and more complex.