A Guidebook to Mechanism in Organic Chemistry

Index

1

Hydrogen bonding—continued
in keto/enol tautomerism, 219
„ salicylic acid, 47
Hydrogen bromide, addition
allyl bromide, 245
electrophilic, 141
1-methylcyclohexene, 246
propylene, 141, 244
radical, 244
stereochemistry, 246
vinyl bromide, 142
Hydroperoxides, 100,252
1,2-Hydroxy amines, conversion to,
pinacolones^L
Hydroxylatiofl
alkenes, 145
via epoxides, 146
, with KMnO„ 145
„ Os0 4 ,145
Hyperconjugation, 20, 62,197, 201
Irnino-etners, formation, 188
Inductive effect, 15,116
Inductomeric effect, 20
Ingold, 58
Inhibitors, 232
Initiators, 232, 247, 249, 252
Ion pair, 14, 69, .80,109,208
Ions, solvation, 39,40,60
Isomerisation, cis-*-trans, 243
Iso-ozonides, 148
Isotactic polymers, 248
Ka, 39
Kfc,48
Ketals, 163
Ketene, decomposition, 258
jS-Keto acids, decarboxylation, 229
/9-Ketoesters, 'acid decomposition',
178
Ketones
bromination, 226, 227
oxidation, 99
Kolbe electrolytic synthesis, 237
Kotbe-Schmid^Mction, 225
tyls, t^^nal decomposijjon,

1

,93

Ifjflr'^Mr'w

[reduction^|66

6,117 ^

ng groups, 121

Methane, acidity, 210

Michael reaction 155

Molozonides, 148

Naphthalene

delocalisation energy, 13

electrophilic substitution, 127

Neighbouring group participation, 70

Neopentyl rearrangement, 87

Ninhydrin, 162

Nitration, 104

kinetics, 105

no isotope effect in, 36,105

with dilute HNO„ 106

„ nitrating mixture, 104

Nitriles

addition, 188

hydrolysis, 188

Nitrogen, migration to electron-defi­

cient, 93-98

Nitromethane, acidity, 211

Nitronium ion, 104

Nitrosation

amines, 75,85

phenol, 106

Nitroso amines, 76

Nitrosonium ion, 75,106

Nucleophilic addition to activated

C=C bonds, 153

Nucleophilic addition to C=0,

158-188

effect of pH, IIP _

effect of structure, 159,183 •

stereochemistry, 181 •

Nucleophilic reagents (nucleophiles),

26, 27, 72

Nucleophilic substitution, aliphatic,

58-79

alcohols with SOC1,, 69

allyl halides, 63

alkylation of reactive methylenes, 77,

(^221) t
benzyl halides, 63
1-bromotriptycene, 65 •
t-butyl chloride, 59
/?-chlorohydrins, 70
effect of Ag®, 82
„ „ entering group, 72
„ „ leaving group, 73
„ „ solvent, 60
„ '•>„ structure, 61
a-halogeno-acids, 71
H® as catalyst, 74
Is .. ,. ,74
kinetics, 58
list of reactions, 76
mechanism, 58
methyl bromide, 58
neighbouring group participation, 70
neopentyl halides, 65