r
IndexBromination
aromatic, 106,250
Lewis acids in, 106
Bromine addition
acetylene dicarboxylic acid, 140
cyclopentene, 36
ethylene, 137,243
maleic acid, 139
styrene, 141
1,2-Bromohydrins, pinacolones from,
90
Bromonium ions, 138, 246
N-Bromosuccinimide, 251
1-Bromotriptycene, 65
Cannizzaro reaction, 35,167
Canonical structures, 12
Carbanions, 14,210-230
addition reactions, 155, 170-180
displacement reaction, 221-230
elimination reactions, 193, 203
formation, 211
from acetaldehyde, 173
„ acetone, 173, 226
„ acetylene, 172,211,222
„ acid anhydrides, 176
„ aliphatic nitro-compounds,
174, 212,220
„ azomethines, 216
„ cyclopentadiene, 212
„ diethyl malonate, 156,221
„ esters, 176 »
It organo-metallic compounds,
238 *
„ triphenylmethane, 210,213
in alkylation, 221
„ benzoin condensation, 179
„ bromination of ketones, 226
„ decarboxylation, 228
„ Reimer-Tiemann reaction, 224
„ tautomerism, 215-221
„ Wurtz reaction, 223
stabilisation, 211
stereochemistry, 213
Carbenes, 93, 207, 224
Carbon atom, 1
Carbon-carbon bond
double, 5,137,157
energy in acetylene, 7
„ „ ethane, 6
„ „ ethylene, 6
lengths in acetylene, 7
„ „ benzene, 9
„ „ ethane, 6
„ „ ethylene, 6
single, 4
triple, 7
Carbonium ions, 14, 80-93
addition to alkenes, 144
allyl, 63, 83Carbonium ions—continued
benzyl, 63,83
cycloheptatrienyl, 84
formation, 80.
intermediates in Swl, 59, 62, 63; 68
loss of H® from, 84, 88
/?-phenylethyl, 83
planar, 60, 68
reactions, 84
rearrangement, 86-93
stabilisation, 62, 82
tropylium, 84
Carbonyl group, 158-188
hydration, 160^^^
nature of, 16, raPV
protection, 163
reaction with acetylide ion, 172
„ „ alcohol's, 162
„ „ aldehydes and ketones,
172
„ „ aliphatic nitro-com
pounds, 174
„ „ amino-compounds,
164
„ „ carbanions, 170-180
„ „ Grignard reagents, 170
„ „ metals, 168
„ „ thiols, 163
reactivity of, in acid chlorides, 183
„ „ „ aldehydes, 159
amides, 159,183
esters, 159,183
„ „ „ ketones, 159
reduction with Al(OCHMe 2 )„ 166
„ LiAlH 4 ,165
stereochemistry of addition to, 181
Carboxylic acid derivatives, reactivity
of, 183
Chain reactions, 231, 243, 244, 247,
248,251,252,253
initiation, 231,242,244, 247,260
propagation, 231,242, 245, 247, 260
termination, 231, 243, 246, 247
transfer agents, 248
Chloral hydrate, 161
Chldrination, aromr*:c, with HOC1,
107 'V -*
Chifcaev reaction, 20i-
Claislb ester condensj
mixed, 178
reve£ibi|jty, 178
ClaiseSgchmidt qondeitdtion, 175,
Ition
Mention in neighboring
group jMticipationAO
determinaMP^j relaafc. 66.
invprfon in SnT
r^ention in SnI, 69^
Conformation, 4
eclipsed and staggered, <- -*
on,