Index
Abbreviations
amino acids, Table 500–1
nucleic acids 551
nucleotides, Table 551
peptides and proteins 504
phosphates and diphosphates 277
structural, Table 14
ACE (angiotensin-converting enzyme)
enzyme action 532
inhibitors 532
Acetal
in etoposide 233
formation 229
polysaccharides as polyacetals 232
as protecting group 230
Acetal and ketal
cyclic, as protecting groups 481
groups in sucrose 231
Acetaldehyde, basicity 139
Acetamide, basicity 139
Acetaminophen, see paracetamol
Acetoacetyl-CoA, biosynthesis from
acetyl-CoA 392
Acetobromoglucose
in glucoside synthesis 479
synthesis 479
Acetone
acidity 130
basicity 139
resonance structures 49
Acetonide
definition 481
of galactose 482
of glucose 482
Acetonitrile
acidity 365
basicity 138
Acetyl coenzyme A, see acetyl-CoA
Acetyl nitrate, in nitration reactions 422
Acetylacetone
acidity 130, 349
alkylation 357
hydrogen bonding 50
Acetylcholine
hydrolysis via acetylcholinesterase 279, 519
receptor sites 202, 211
muscarinic 413
nicotinic 413
as quaternary ammonium salt 202
Acetylcholinesterase
enzyme mechanism 519–21
hydrolysis of acetylcholine 279
inhibitors 279
Acetyl-CoA carboxylase, in fatty acid
biosynthesis 595
Acetyl-CoA (acetyl coenzyme A)
as acylating agent 262
carboxylation to malonyl-CoA 595,
609
Claisen reaction 381
enolate anions 373
in Krebs cycle 585
from β-oxidation of fatty acids 388
as thioester 262, 373
Acetylene, bonding molecular orbitals 31
Acetylenes, acidity 128
N-Acetylgalactosamine, in blood group
antigens 496
N-Acetylglucosamine
in chitin 495
in peptidoglycan 495, 538
Acetylide anion 156
Acetylides
formation 205, 240
as nucleophile in S N 1 and S N 2 reactions
205
as nucleophile with aldehydes and ketones
241
N-Acetylmuramic acid, in peptidoglycan 495,
538
Acetylsalicylic acid, see aspirin
Achiral molecules 74
Aciclovir, structure 559
Acid
Brønsted–Lowry definition 121
conjugate see conjugate acid
Lewis definition 121
polyfunctional 144
strong 122
strong, pH calculation 146
weak 122
weak, pH calculation 147–8
Acid–base
catalysis, enzymes 516
equilibria 121
interactions, predicting 155–7
Acidic reagents, Table 157
Acidity
acidity constant 122
bond energy effects 125
definition 121
electronegativity effects 125
hybridization effects 128
inductive effects 125–7
influence of electronic and structural
features 125–34
and leaving groups, Table 189
pK a values 122–5
resonance / delocalization effects 129–34
Acidity (compounds)
acetone 130
acetonitrile 365
acetylacetone 130, 349
acetylenes 128
acrylic acid 128
adenine 450
alcohols 125, 127
amides 372
benzoic acid 128, 130
benzoic acids, substituted 131–3
carboxylic acids 125
carboxylic acids, halogenated 125
carboxylic acid derivatives, Table 372
cyclohexanecarboxylic acid 130
cyclohexanol 133
cyclopentadiene 421
dicarboxylic acids
aliphatic 144
aromatic 145
diethyl malonate 390
esters 372
ethane 128
ethyl acetoacetate 380
ethylene 128
glutaric acid 144
Essentials of Organic Chemistry Paul M Dewick
© 2006 John Wiley & Sons, Ltd
Abbreviations
amino acids, Table 500–1
nucleic acids 551
nucleotides, Table 551
peptides and proteins 504
phosphates and diphosphates 277
structural, Table 14
ACE (angiotensin-converting enzyme)
enzyme action 532
inhibitors 532
Acetal
in etoposide 233
formation 229
polysaccharides as polyacetals 232
as protecting group 230
Acetal and ketal
cyclic, as protecting groups 481
groups in sucrose 231
Acetaldehyde, basicity 139
Acetamide, basicity 139
Acetaminophen, see paracetamol
Acetoacetyl-CoA, biosynthesis from
acetyl-CoA 392
Acetobromoglucose
in glucoside synthesis 479
synthesis 479
Acetone
acidity 130
basicity 139
resonance structures 49
Acetonide
definition 481
of galactose 482
of glucose 482
Acetonitrile
acidity 365
basicity 138
Acetyl coenzyme A, see acetyl-CoA
Acetyl nitrate, in nitration reactions 422
Acetylacetone
acidity 130, 349
alkylation 357
hydrogen bonding 50
Acetylcholine
hydrolysis via acetylcholinesterase 279, 519
receptor sites 202, 211
muscarinic 413
nicotinic 413
as quaternary ammonium salt 202
Acetylcholinesterase
enzyme mechanism 519–21
hydrolysis of acetylcholine 279
inhibitors 279
Acetyl-CoA carboxylase, in fatty acid
biosynthesis 595
Acetyl-CoA (acetyl coenzyme A)
as acylating agent 262
carboxylation to malonyl-CoA 595,
609
Claisen reaction 381
enolate anions 373
in Krebs cycle 585
from β-oxidation of fatty acids 388
as thioester 262, 373
Acetylene, bonding molecular orbitals 31
Acetylenes, acidity 128
N-Acetylgalactosamine, in blood group
antigens 496
N-Acetylglucosamine
in chitin 495
in peptidoglycan 495, 538
Acetylide anion 156
Acetylides
formation 205, 240
as nucleophile in S N 1 and S N 2 reactions
205
as nucleophile with aldehydes and ketones
241
N-Acetylmuramic acid, in peptidoglycan 495,
538
Acetylsalicylic acid, see aspirin
Achiral molecules 74
Aciclovir, structure 559
Acid
Brønsted–Lowry definition 121
conjugate see conjugate acid
Lewis definition 121
polyfunctional 144
strong 122
strong, pH calculation 146
weak 122
weak, pH calculation 147–8
Acid–base
catalysis, enzymes 516
equilibria 121
interactions, predicting 155–7
Acidic reagents, Table 157
Acidity
acidity constant 122
bond energy effects 125
definition 121
electronegativity effects 125
hybridization effects 128
inductive effects 125–7
influence of electronic and structural
features 125–34
and leaving groups, Table 189
pK a values 122–5
resonance / delocalization effects 129–34
Acidity (compounds)
acetone 130
acetonitrile 365
acetylacetone 130, 349
acetylenes 128
acrylic acid 128
adenine 450
alcohols 125, 127
amides 372
benzoic acid 128, 130
benzoic acids, substituted 131–3
carboxylic acids 125
carboxylic acids, halogenated 125
carboxylic acid derivatives, Table 372
cyclohexanecarboxylic acid 130
cyclohexanol 133
cyclopentadiene 421
dicarboxylic acids
aliphatic 144
aromatic 145
diethyl malonate 390
esters 372
ethane 128
ethyl acetoacetate 380
ethylene 128
glutaric acid 144
Essentials of Organic Chemistry Paul M Dewick
© 2006 John Wiley & Sons, Ltd