Organic Chemistry Mechanistic Patterns

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Chapter 5
Organic Reaction Mechanisms:
Using Curved Arrows to Analyze Reaction Mechanisms

CHECKPOINT PROBLEMS

Practice Problem 5.1

a)
b) Note: the carbamate functional group is not included in Table 2.1.

Ketones (circled with lone pairs added) Amines (circled with lone pairs added)

O O
N NH N NH

H 2N O O
H 2N
O O
O O
H2N O H2N O

Alkenes Other groups (labelled and

(circled) circled with lone pairs
added)

O O

N NH
N NH
H 2N O
H 2N O
O
O O ether
O carbamate
(see H2N O
H2N O note)

5-2
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5-2
c) Esters (circled and lone pairs added) Alcohols (circled and lone pairs added)

O O
O O OH O O OH

O NH O O NH O

O H O O O
H

OH OH O O O
OH OH O

O O O
O

Phenyls (circled) Other groups (labelled and circled with

lone pairs added)

O amide
alkene ketone
O O OH
O

O O OH
O N O

O O O NH O
H
OH OH O O
O H O

O OH OH O O
O
O O ether

Integrate the Skill 5.2

There are many possible answers to the question. One is shown below.

5-3
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5-3
Practice Problem 5.3
a) Here, both of the bonding electrons go to nitrogen. The bond was formally one electron from
N and one from C. Since both are now on N, the nitrogen has gained an electron and the
carbon has lost an electron, leading to the final charge location on C.

b) The hydroxide ion contributes both electrons in forming the new C–O bond and so has
formally lost a valence electron. The carbon still has four valence electrons and so remains
neutral. The carbonyl oxygen gained a valence electron, as it is no longer sharing the bond
electron with carbon, and is negatively charged.

c) The new bond introduces charges on the boron and oxygen atoms, as indicated.

d) A new C–H bond forms from the CH3⊝ lone pair electrons and the broken C–H bond
electrons end up on the alkyne carbon.

5-4
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5-4
e) The Cl⊝ removes an H to make HCl. The C–H bond electrons make a new π bond.

f) A new C–H bond forms by formal addition of H⊝ to the C=O carbon.

Integrate the Skill 5.4

a) The product is incorrect. A benzene ring and HBr would form, as in part (e) of Practice
Problem 5.3.

b) The mechanism was missing the arrow for movement of the C=N double bond electrons to
the N atom.

c) The lone pair electrons on O make the bond to H. The arrow was pointing in the wrong
direction. As well, adding lone pair electrons on the O is recommended when one is just
getting started working with mechanisms.

5-5
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5-5
Another document from Scribd.com that is
random and unrelated content:
Macedonia regained her supremacy in Greece, and the power of the
Achaean League was broken.

The old Greece of history no longer existed. Greek civilization had

spread over the Mediterranean world, but the free and independent city-
state had disappeared and nothing lasting had taken its place. Alexander
himself, and still more his successors, had failed to create an empire
which gave to those who belonged to it any sense of citizenship in it. The
Hellenistic world was a Greek civilization, but it failed to arouse in men
of Greek birth that patriotism which the city-state had inspired.

The creation of a world state of which men were to be proud to call

themselves citizens and for which they would gladly die, was to be the
work of another great power, which even as the old Greece was passing,
was growing strong in the West. Rome was steadily conquering the
civilized world. Already she ruled over Italy and was extending her
power over the Eastern Mediterranean. She conquered Macedonia, and
one by one the old free states of Greece and those of the Achaean League
lost their independence, until in 146 B.C. Corinth, rich, commercial, gay
Corinth, was taken by Rome, and Greece became a Roman province. The
citizens of this great state, which was to include, not only Greece and the
Levant, but the whole Mediterranean and lands far beyond its shores,
were to be proud of the name of Roman. Yet Rome, destined to be the
Mistress of the World, and in political power an empire, succeeding
where Greece had failed, owed all that was most worth while in the
things of the higher intellectual life of the mind to Greece. The Greek
spirit was never to die.

[1] From Athenaeus.

SUGGESTIONS ABOUT BOOKS FOR FURTHER

READING
 This book has been intended for those who were reading about Greece
for the first time. The following list is for those older readers of the book
who would like to know more about this great civilization. It only
contains suggestions as to how to begin, and is therefore not in any way
a complete bibliography.

I. Books about Greece

GROTE. History of Greece. This book was written some time ago, but it
is still the most famous history of Greece.

C. H. and H. B. HAWES. Crete the Forerunner of Greece.

BAIKIE. The Sea Kings of Crete.

R. W. LIVINGSTONE. The Greek Genius and its Meaning to Us.

R. W. LIVINGSTONE. (Edited by) The Pageant of Greece.

R. W. LIVINGSTONE. (Edited by) The Legacy of Greece.

GILBERT MURRAY. The Rise of the Greek Epic.

A. E. ZIMMERN. The Greek Commonwealth.

E. N. GARDINER. Greek Athletic Sports and Festivals.

ETHEL B. ABRAHAMS. Greek Dress.

EMILY JAMES PUTNAM. The Lady.

E. POTTIER. Douris and the Painters of Greek Vases.

G. M. A. RICHTER. The Craft of Athenian Pottery.

G. M. A. RICHTER. Handbook to the Classical Collection in the

Metropolitan Museum, New York. An excellent introduction to the study
of Greek Art.

KENNETH J. FREEMAN. The Schools of Hellas.

A. E. HAIGH. The Attic Theatre.

E. A. GARDNER. A Handbook of Greek Sculpture.

D. G. HOGARTH. Philip and Alexander.

PUTNAM. Authors and their Public in Ancient Times.

MAHAFFY. Social Life in Greece.

MAHAFFY. Alexander's Empire.

II. Greek Writers

No reading about Greece can take the place of reading what the
Greeks themselves wrote. References to Greek writers will have been
found all through this book and in the list of acknowledgments at the
beginning. The following list of the more important writers and their
works referred to in this book has been put together for the purpose of
easier reference.

HOMER. The Iliad, translated by Lang, Leaf and Myers.

HOMER. The Odyssey, translated by Butcher and Lang.

HOMER. The Homeric Hymns, translated by Andrew Lang.

AESCHYLUS. Translated by A. S. Way and also by E. M. Cookson.

AESCHYLUS. The Agamemnon, translated by Gilbert Murray.

SOPHOCLES. Translated by R. C. Jebb.

SOPHOCLES. Oedipus, King of Thebes, translated by Gilbert Murray.

EURIPIDES. Translated by Gilbert Murray.

ARISTOPHANES. Translated by B. B. Rogers.

The Frogs, translated by Gilbert Murray.

PLATO. Translated by Benjamin Jowett.

PLATO. The Republic, translated by Davies and Vaughan.

PLATO. Trial and Death of Socrates, translated by F. J. Church.

ARISTOTLE. Politics, translated by Benjamin Jowett and also by J. E.

C. Welldon.

HERODOTUS. Translated by G. C. Macaulay.

THUCYDIDES. Translated by Benjamin Jowett.

XENOPHON. Translated by H. G. Dakyns.

PLUTARCH. Translated by Dryden, revised by A. H. Clough.

DEMOSTHENES. Public Orations, translated by A. W. Pickard-

Cambridge.

The Claim of Antiquity, an excellent pamphlet published by the

Oxford University Press, gives a much fuller and more complete list of
books and translations for those who would like further suggestions.

III. Greek Sculpture and Architecture

Not every one can go to Greece or even to Sicily, but most museums
have good collections of casts and models. Greek sculpture is not all
found in one place, but scattered through the museums of the world.
Those who can go to London, Paris, Rome and Naples, if nowhere else,
can get first-hand knowledge of some of the greatest things the Greeks
produced. For the sculptures from the Parthenon are in the British
Museum; most beautiful things are in the Museo delle Terme in Rome (to
see the other half of the Throne of Aphrodite one must go to the Museum
of Fine Arts in Boston, Massachusetts), and Sophocles is in the Museum
of the Lateran. From Naples one can go to Paestum, once the Greek
colony of Poseidonia, famous in ancient times for its roses, and see the
Temple of Poseidon. It has never been restored, and is one of the best
preserved Greek temples to be seen anywhere out of Attica. There it
stands, as it has stood for over two thousand years, looking out towards
the sea, solitary, now, and desolate, yet in its loneliness most beautiful.

All these things are merely suggestions as to one way of beginning.

Those who begin will find no difficulty in going on.

INDEX

Academy, 194, 211, 381

Achaean League, 407
Acropolis, 91, 190, 194; temples on, 278 ff.; later history of 284 ff.
Aegean civilization, 5
Aeschylus, 107, 163, 390, 395, 402, 412
Aethiopians, 44
Agamemnon of Aeschylus, 391, 395, 412
Agamemnon, Tomb of, 6, 25, 26
Agora, 191, 207
Alaric the Goth, 284
Alcestis of Euripides, 393, 412
Alcibiades; early life of, 302 ff.; Sicilian expedition, 305 ff.; summoned
to Athens, 309; the traitor, 310 ff.; recalled to Athens, 314; exiled,
315
Alcmaeonids, 104
Alexander; youth and education, 342 ff.; policy, 345; conquests of 347
ff.; death of, 356; empire of, 398, 406
Alexandria, 400 ff.; Museum at, 401; Library, 401; book-publishing in,
402; science in 404 ff.
Alexandrian editions, 403
Amphipolis, 301
Amphora, 203
Anabasis of Xenophon, 318, 320, 412
Anaximander, 112
Antigone of Sophocles, 392, 412
Aphrodite, 51
Apollo, 48, 52, 53
Apology of Socrates, 371, 373, 374
Aratus, 407
Archimedes, 404
Architecture, 277 ff.
Archon, 94
Ariadne, 7
Aristeides; character of, 156; rivalry with Themistocles, 156; ostracism
of, 158; return of, 162; forms Delian League, 180
Aristophanes; comedies of, 209, 300, 393, 412
Aristotle; Politics of, 72, 384, 412; views on education, 227, 384; tutor
to Alexander the Great, 344; at the Lyceum, 383; will of, 383;
"Father of Natural Science," 383
Artaxerxes, 317
Artemis, 49, 217
Artemisium, 149
Athena, 47, 48, 50; birth of, 280; contest with Poseidon, 92, 281; symbol
of Athens, 283
Athenian Dress, 195 ff.
Athenian Education, 221 ff.
Athenian Government; rule of one man, 91 ff.; oligarchy, rule of the few,
94 ff.; rule of the many, 96 ff.
Athenian House, 198
Athenian Life, 190 ff.
Athenian Pottery, 203 ff.
Athenian Trade, 201
Athens; situation and appearance, 190 ff.; classes of people, 194; burnt
by Xerxes, 161; burnt by Mardonius, 168; during Persian War, 144;
Long Walls, 173, 298; fortifications of, 172; becomes an empire, 183;
enemies of, 291 ff.; during Peloponnesian War, 296 ff.; downfall of,
315
Athos, Mount, 126
Arrian, 334, 349, 351, 353
Assembly; Spartan, 79; Athenian, 210, 299

Banquet of Xenophon, 225, 412

Bema, 210
Brasidas, 301
Byzantium, 110, 175

Cadmus, 324
Callimachus, 403
Caryatid, 280
Cecrops, 91
Cerameicus, 204
Chaeronea, 332
Chios, 112, 125, 202
Chiton, 195
Chlamys, 196
Cimon, 93
Citizenship, Greek ideals of, 73 ff.
City-State, 70 ff.
Cleon, 301
Clio, 49
Clouds of Aristophanes, 300, 412
Colonies, 108 ff.; Ionian, 110 ff.; in Italy, 113; in Sicily, 113; in Egypt,
113
Constitution of the Lacedaemonians of Xenophon, 88
Corinth; council at, 145; urges Sparta to make war on Athens, 291; fall
of, 408
Crete, 6 ff.; legends of, 7 ff.; dress, 11; writing, 15; religion, 13; life in,
16 ff.; amusements, 18
Crito, 374
Croesus, 100 ff.; conquers Ionian colonies, 115; war with Cyrus, 116
Cunaxa, 319
Cylon, 103
Cyrus the Great, 115; conquers Sardis, 116; conquers Ionian colonies,
117
Cyrus the Younger, 318 ff.

Daedalus, 8
Darius, 118 ff.; Scythian expedition of, 118 ff.; determines to invade
Greece, 124, 126
Delos, 128; Confederacy of, 180
Delphi, 43; oracle at, 57 ff.; Treasury of Athenians at, 134
Demeter, 54 ff.
Demosthenes, 335 ff.; 412
Deucalion, 42
Diogenes, 346
Dionysus, 232
Dodona, 57
Dorians, 75
Draco, 98
Drama, 233
Dramatists; Aeschylus, 390; Aristophanes, 393; Euripides, 392;
Sophocles, 392
Dress; Athenian, 195; Cretan, 11; Homeric, 28

Economist of Xenophon, 198, 215, 216, 412

Education; Athenian, 221 ff.; Spartan, 84 ff.
Electra of Euripides, 393, 412
Eleusis, 54, 220
Elysian Fields, 44
Empire; Athenian, 183, 282; Alexander's, 398, 406
Epaminondas, 325 ff.
Ephors, 80
Erechtheum, 279
Eretria; joins Ionian revolt, 123; burnt by Persians, 128
Euclid, 404
Euripides, 39, 109, 226, 234, 238, 300, 392 ff., 402, 412
Evans, Sir Arthur, 12

Funeral Speech, 187

Games; Isthmian, 61; Olympic, 60 ff.; Pythian, 61

Gordian Knot, 347
Greece; divisions of, 37; trees of, 37; products of, 38; climate of, 39
Greek Art, 394 ff.
Greek Characteristics, 40
Greek Spirit, 102, 358

Hades, 54 ff.
Hecataeus, 112
Hellenic Period, 399
Hellenica of Xenophon, 315,316, 327, 412
Hellespont, 141
Hellenistic Age, 398 ff.
Helots, 76
Hephaestus, 50
Hera, 47
Hermes, 49, 106
Hermes of Praxiteles, 222, 395
Herodas, translation from Mime III, 228 ff.
Herodotus, 39, 78, 111, 115, 117, 118 ff., 136 ff., 174, 282, 385 ff., 412
Hestia, 51, 52, 199
Himation, 196
Hipparchus, 106
Hippias, 106, 128
Hippolytus of Euripides, 234, 412
Historians; Herodotus, 385 ff.; Plutarch, 389; Thucydides, 386 ff.;
Xenophon, 388
Homer, 22, 58, 112, 225, 411
Homeric Age, 27 ff.; dress, 28; palaces, 28 ff.; furniture, 30 ff.
Homeric Hymns, 47, 48, 49, 50, 51, 52, 54, 55, 58, 281, 411
Houses; Athenian, 198 ff.; Cretan, 16; Homeric, 28
Hydria, 203
Hyperboreans, 43

Iliad, 6, 8, 19, 20, 22, 46, 68, 106, 402, 411

Ionian Colonies, 110, 202; conquered by Croesus, 115; conquered by
Cyrus, 117; appeal to Athens for help, 174
Ionian Revolt, 122
Iphigenia in Tauris of Euripides, 238 ff.; 393, 412
Isthmian Games, 61

King's Peace, 317

Knights of Aristophanes, 300, 412
Knossos, 8; palace of, 10; destruction of, 20
Krater, 203

Lacedaemonians, 75
Laconia, 75
Lade, 124
Laurium, 156
Lawgivers; Draco, 98; Lycurgus, 76 ff.; Solon, 96 ff.
Lekythos, 203
Leonidas, 148
Lesbos, 112
Leuctra, 327
Long Walls, 173, 298, 316
Lyceum, 383
Lycurgus, 76 ff.; travels of, 77; at Delphi, 78; government of, 76 ff.;
death of, 90
Lydia, 114

Macedonians, 329
Magna Graecia, 113
Mantinea, 327
Map-makers, 112
Marathon, 130 ff.
Mardonius, 125, 137, 166, 168
Mediterranean, 3 ff.
Memorabilia of Xenophon, 278, 373
Metopes, 282
Minoan Civilization, 8
Minos, 7
Miletus, 111, 202; siege of by Lydia, 114; revolt against Darius, 122; fall
of, 124
Militiades, 131
Muses, 49
Music, 227
Mycenae, 25 ff.; 32
Mycenaean Civilization, 5

Naucratis, 113
Naxos, 122, 127
Nicias, 302
 O

Odyssey, 7, 8, 19, 22, 29, 30, 50, 402, 411

Oedipus at Colonus of Sophocles, 392, 412
Oedipus the King of Sophocles, 392, 412
Oligarchy, 94
Olympia; oracle at, 57; statue of Zeus at, 64
Olympic Games, 60 ff.
Olympus, 43, 46
Oracle; origin of, 56; oracles of Zeus, 57; of Apollo, 57
Oracles; about Homer, 58; given to Lycurgus, 78; to Cylon, 103; to
Spartans, 107; "deceitful answer" to Croesus, 115; of the wooden
walls, 159
Orations; Funeral Speech of Pericles, 187 ff.; of Demosthenes, from
Third Philippic, 338; from Second Olynthiac, 339; On the Crown,
339 ff.
Ostracism, 157

Palaestra, 227
Pan, 51, 129, 134
Panathenaic Festival, 204, 217, 283
Parnassus, 42, 49
Parthenon, 280 ff.
Pausanias, Spartan General; at Plataea, 168 ff.; at Byzantium, 175;
suspicious conduct of, 175; death of, 176
Pausanias the Traveller, 25, 64, 69
Pedagogue, 223
Pediment, 277
Peiraeus, 173, 202
Peisistratus, 104 ff.
Pelopidas, 326
Peloponnesian War; causes, 291 ff.; course of war, 296 ff.; Sicilian
Expedition, 305 ff.; defeat of Athens, 315 ff.
Pentathlon, 67
Pericles, 53; early life of, 183; leader of Athens, 185; Funeral Speech of,
187 ff.; beautifies Athens, 289; policy during Peloponnesian War,
297; death of, 298; imperial policy of, 298 ff.
Persephone, 54 ff.
Persians of Aeschylus, 163, 412
Persian Wars, 118 ff.; invasion under Mardonius, 125; Marathon, 125 ff.;
invasion under Xerxes, 136 ff.; Thermopylae, 148 ff.; Salamis, 161
ff.
Phaedo of Plato, 375, 377
Phaedrus of Plato, 382, 412
Pheidias, 46, 64, 279, 395
Pheidippides, 129, 132
Philip of Macedon, 328; King of Macedonia, 330; policy of, 330;
conflict with Greek states, 331 ff.; destroys Thebes, 332; death of,
333
Philippics of Demosthenes, 338, 412
Philosophers; Aristotle, 72, 227, 383 ff., 412; Plato, 380 ff., 412;
Pythagoras, 379; Socrates, 361 ff; Thales, 111, 379
Philosophy, Greek, 378
Pindar, 69, 323
Plague in Athens, 297
Plataea; aids Athens before Marathon, 131; battle of, 168
Plato, 57, 194, 225, 226, 228, 363, 367, 371, 373, 374, 375, 377, 380 ff.,
412
Plutarch, 75, 90, 93, 96, 154, 156, 158, 172, 177, 178, 180, 181, 185,
186, 284, 298, 304, 309, 310, 314, 336, 337, 345, 346, 389, 412
Pnyx, 210
Polemarch, 94
Politics of Aristotle, 72, 384, 412
Poseidon, 47, 92, 281
Praxiteles, 222, 395
Propylaea, 278
Protagoras of Plato, 225, 412
Ptolemy Philadelphia, 401
Ptolemy Soter, 401
Pyrrha, 42
Pythagoras, 379
Pythian Games, 60
 R

Religion; Cretan, 13; Greek, 44 ff.

Republic of Plato, 226, 381, 412

Sacred Mysteries, 54 ff., 220

Salamis, 97; battle of, 163 ff.
Sappho, 112
Sardis; taken by Cyrus, 116; burnt by Ionians, 123; Persian army at, 138
Schliemann, 23 ff.
Science; in Ionia, 111; in Alexandria, 404 ff.
Scythia, 118
Senate, Spartan, 78
Septuagint, 403
Sicily, 113
Sicilian Expedition, 305 ff.
Socrates, 278, 303, 396; early life, 361 ff.; Socrates and the Sophists,
364; Socratic method of teaching, 366; accusations against, 368; trial
off 368; Apology of, 368 ff.; death of, 374 ff.
Solon; early life of, 96; war over Salamis, 97; Archon, 98; reforms of, 98
ff.; travels of 100; Solon and Croesus, 100 ff.
Sophists, 364
Sophocles, 392, 395, 402, 412
Sparta; situation of, 75; government of, 76 ff.; customs, 81 ff.; education,
845.; position of women, 89; aids Athens in expelling Hippias, 107;
refusal to join Ionian revolt, 123; refuses immediate help before
Marathon, 129; at Thermopylae, 148 ff.; jealousy of Athens, 172 ff.;
policy towards Ionian colonies, 174; during Peloponnesian War, 287
ff.; supremacy of, 316
Sphacteria, 301
Statues; Zeus at Olympia, 64; Hermes of Praxiteles, 222; Athena
Promachos, 279, 284; Athena Polias, 280; Athena Parthenos, 283;
Sophocles, 413
Stoa, 193
Strabo, 4
Symposium, 213
Symposium of Plato, 363, 367, 412
Syracuse, 113, 226, 405; battle in harbour of, 312

Temples, 14, 276 ff.; Athena Nike, 279; Erechtheum, 279; Parthenon,
280 ff.; Paestum, 413
Ten Thousand, March of the, 318
Thales, 111, 379
Theatre, 232 ff.
Thebes, 153, 317; early history of, 322; legends of, 324; supremacy of,
325 ff.; defeated by Philip of Macedon, 332; destroyed by Alexander,
346
Themistocles; early life and character, 153; at Artemisium, 150; builds a
navy, 155; rivalry with Aristeides, 156; at Salamis, 161 ff.; popularity
of, 171 ff.; fortifies Athens, 172; accusations against, 176; ostracized,
177; at the Persian court, 177; death of, 178
Theocritus, 216
Therma, 143
Thermopylae, 148 ff.
Theseus, 7, 92, 93; ship of, 9, 374
Thucydides, 7, 155, 181, 189, 297, 302, 308, 309, 314, 360, 386 ff., 412
Tiryns, 27;
Trojan War, 22, 347
Trojan Women of Euripides, 39, 300, 412
Troy, discovery of, 24
Tyrants, 102 ff.; Cylon, 103; Peisistratus, 104 ff.

Wasps of Aristophanes, 209, 300, 412

Women, position of; in Athens, 214 ff.; in Sparta, 89
Writing, Cretan, 15

X
Xanthippe, 363
Xenophon, 88, 198, 214, 215, 216, 225, 278, 314, 315, 318, 327, 373,
388, 412
Xerxes, 136 ff.

Zeus, 7, 46, 52, 53, 199, 231

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