The art of writing reasonable organic reaction mechanisms:
Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is t...
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
New York [u.a.]
Springer
2003
|
| Ausgabe: | 2. ed. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Zusammenfassung: | Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. (Midwest). |
| Beschreibung: | XVI, 355 S. graph. Darst. : 25 cm |
| ISBN: | 0387954686 |
Internformat
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| 100 | 1 | |a Grossman, Robert B. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a The art of writing reasonable organic reaction mechanisms |c Robert B. Grossman |
| 250 | |a 2. ed. | ||
| 264 | 1 | |a New York [u.a.] |b Springer |c 2003 | |
| 300 | |a XVI, 355 S. |b graph. Darst. : 25 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 520 | 3 | |a Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. (Midwest). | |
| 650 | 7 | |a Réactions chimiques organiques - Mécanismes |2 ram | |
| 650 | 4 | |a Réactions organiques (Chimie) | |
| 650 | 4 | |a Organic reaction mechanisms | |
| 650 | 0 | 7 | |a Reaktionsmechanismus |0 (DE-588)4177123-0 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Chemische Reaktion |0 (DE-588)4009853-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Organische Chemie |0 (DE-588)4043793-0 |2 gnd |9 rswk-swf |
| 655 | 7 | |8 1\p |0 (DE-588)4151278-9 |a Einführung |2 gnd-content | |
| 655 | 7 | |8 2\p |0 (DE-588)4123623-3 |a Lehrbuch |2 gnd-content | |
| 655 | 4 | |a Matériel didactique | |
| 689 | 0 | 0 | |a Organische Chemie |0 (DE-588)4043793-0 |D s |
| 689 | 0 | 1 | |a Chemische Reaktion |0 (DE-588)4009853-9 |D s |
| 689 | 0 | 2 | |a Reaktionsmechanismus |0 (DE-588)4177123-0 |D s |
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| 883 | 1 | |8 2\p |a cgwrk |d 20201028 |q DE-101 |u https://d-nb.info/provenance/plan#cgwrk | |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-010241452 | |
Datensatz im Suchindex
| _version_ | 1808226042278576128 |
|---|---|
| adam_text |
CONTENTS
PREFACE
TO
THE
STUDENT
V
PREFACE
TO
THE
INSTRUCTOR
IX
1
THE
BASICS
1
1.1
STRUCTURE
AND
STABILITY
OF
ORGANIC
COMPOUNDS
.
1
1.1.1
CONVENTIONS
OF
DRAWING
STRUCTURES;
GROSSMAN
'
S
RULE
.
1
1.1.2
LEWIS
STRUCTURES;
RESONANCE
STRUCTURES
.
3
1.1.3
MOLECULAR
SHAPE;
HYBRIDIZATION
.
9
1.1.4
AROMATICITY
.
13
1.2
BRPNSTED
ACIDITY
AND
BASICITY
.
16
1.2.1
PK
A
VALUES
.
16
1.2.2
TAUTOMERISM
.
19
1.3
KINETICS
AND
THERMODYNAMICS
.
20
1.4
GETTING
STARTED
IN
DRAWING
A
MECHANISM
.
22
1.5
CLASSES
OF
OVERALL
TRANSFORMATIONS
.
25
1.6
CLASSES
OF
MECHANISMS
.
26
1.6.1
POLAR
MECHANISMS
.
27
1.6.2
FREE-RADICAL
MECHANISMS
.
38
1.6.3
PERICYCLIC
MECHANISMS
.
41
1.6.4
TRANSITION-METAL-CATALYZED
AND
-MEDIATED
MECHANISMS
.
42
1.7
SUMMARY
.
42
PROBLEMS
.
43
2
POLAR
REACTIONS
UNDER
BASIC
CONDITIONS
50
2.1
SUBSTITUTION
AND
ELIMINATION
AT
C(SP
3
)-X
A
BONDS,
PART
I
.
50
2.1.1
SUBSTITUTION
BY
THE
S
N
2
MECHANISM
.
51
2.1.2
^-ELIMINATION
BY
THE
E2
AND
ELCB
MECHANISMS
.
53
2.1.3
PREDICTING
SUBSTITUTION
VS.
ELIMINATION
.
56
2.2
ADDITION
OF
NUCLEOPHILES
TO
ELECTROPHILIC
TT
BONDS
.
58
2.2.1
ADDITION
TO
CARBONYL
COMPOUNDS
.
58
2.2.2
CONJUGATE
ADDITION;
THE
MICHAEL
REACTION
.
67
XIV
CONTENTS
2.3
SUBSTITUTION
AT
C(SP
2
)-X
A
BONDS
.
69
2.3.1
SUBSTITUTION
AT
CARBONYL
C
.
69
2.3.2
SUBSTITUTION
AT
ALKENYL
AND
ARYL
C
.
74
2.3.3
METAL
INSERTION;
HALOGEN-METAL
EXCHANGE
.
78
2.4
SUBSTITUTION
AND
ELIMINATION
AT
C(SP
3
)-X
A
BONDS,
PART
II
.
.
.
80
2.4.1
SUBSTITUTION
BY
THE
S
R
N
1
MECHANISM
.
80
2.4.2
SUBSTITUTION
BY
THE
ELIMINATION-ADDITION
MECHANISM
.
.
81
2.4.3
SUBSTITUTION
BY
THE
ONE-ELECTRON
TRANSFER
MECHANISM
.
82
2.4.4
METAL
INSERTION;
HALOGEN-METAL
EXCHANGE
.
83
2.4.5
A-ELIMINATION;
GENERATION
AND
REACTIONS
OF
CARBENES
.
.
84
2.5
BASE-PROMOTED
REARRANGEMENTS
.
87
2.5.1
MIGRATION
FROM
C
TO
C
.
88
2.5.2
MIGRATION
FROM
C
TO
O
OR
N
.
90
2.5.3
MIGRATION
FROM
B
TO
C
OR
O
.
91
2.6
TWO
MULTISTEP
REACTIONS
.
92
2.6.1
THE
SWEM
OXIDATION
.
92
2.6.2
THE
MITSUNOBU
REACTION
.
94
2.7
SUMMARY
.
95
PROBLEMS
.
97
3
POLAR
REACTIONS
UNDER
ACIDIC
CONDITIONS
105
3.1
CARBOCATIONS
.
105
3.1.1
CARBOCATION
STABILITY
.
106
3.1.2
CARBOCATION
GENERATION;
THE
ROLE
OF
PROTONATION
.
109
3.1.3
TYPICAL
REACTIONS
OF
CARBOCATIONS;
REARRANGEMENTS
.
.
112
3.2
SUBSTITUTION
AND/^-ELIMINATION
REACTIONS
AT
C(SP
3
)-X
.
117
3.2.1
SUBSTITUTION
BY
THE
S
N
I
AND
S
N
2
MECHANISMS
.
117
3.2.2
/3-ELIMINATION
BY
THE
EL
MECHANISM
.
120
3.2.3
PREDICTING
SUBSTITUTION
VS.
ELIMINATION
.
122
3.3
ELECTROPHILIC
ADDITION
TO
NUCLEOPHILIC
C=C
TT
BONDS
.
122
3.4
SUBSTITUTION
AT
NUCLEOPHILIC
C=C
IT
BONDS
.
125
3.4.1
ELECTROPHILIC
AROMATIC
SUBSTITUTION
.
125
3.4.2
AROMATIC
SUBSTITUTION
OF
ANILINES
VIA
DIAZONIUM
SALTS
.
129
3.4.3
ELECTROPHILIC
ALIPHATIC
SUBSTITUTION
.
131
3.5
NUCLEOPHILIC
ADDITION
TO
AND
SUBSTITUTION
AT
ELECTROPHILIC
TT
BONDS
.
132
3.5.1
HETEROATOM
NUCLEOPHILES
.
132
3.5.2
CARBON
NUCLEOPHILES
.
136
3.6
SUMMARY
.
140
PROBLEMS
.
141
4
PERICYCLIC
REACTIONS
148
4.1
INTRODUCTION
.
148
4.1.1
CLASSES
OF
PERICYCLIC
REACTIONS
.
148
4.1.2
POLYENE
MOS
.
154
CONTENTS
XV
4.2
ELECTROCYCLIC
REACTIONS
.
156
4.2.1
TYPICAL
REACTIONS
.
156
4.2.2
STEREOSPECIFICITY
.
163
4.2.3
STEREOSELECTIVITY
.
168
4.3
CYCLOADDITIONS
.
170
4.3.1
TYPICAL
REACTIONS
.
170
4.3.2
REGIOSELECTIVITY
.
183
4.3.3
STEREOSPECIFICITY
.
184
4.3.4
STEREOSELECTIVITY
.
191
4.4
SIGMATROPIC
REARRANGEMENTS
.
195
4.4.1
TYPICAL
REACTIONS
.
195
4.4.2
STEREOSPECIFICITY
.
201
4.4.3
STEREOSELECTIVITY
.
206
4.5
ENE
REACTIONS
.
210
4.6
SUMMARY
.
213
PROBLEMS
.
215
5
FREE-RADICAL
REACTIONS
224
5.1
FREE
RADICALS
.
224
5.1.1
STABILITY
.
224
5.1.2 GENERATION
FROM
CLOSED-SHELL
SPECIES
.
227
5.1.3
TYPICAL
REACTIONS
.
232
5.1.4
CHAIN
VS.
NONCHAIN
MECHANISMS
.
238
5.2
CHAIN
FREE-RADICAL
REACTIONS
.
239
5.2.1
SUBSTITUTION
REACTIONS
.
239
5.2.2
ADDITION
AND
FRAGMENTATION
REACTIONS
.
244
5.3
NONCHAIN
FREE-RADICAL
REACTIONS
.
252
5.3.1
PHOTOCHEMICAL
REACTIONS
.
252
5.3.2
REDUCTIONS
AND
OXIDATIONS
WITH
METALS
.
254
5.3.3
CYCLOAROMATIZATIONS
.
261
5.4
MISCELLANEOUS
RADICAL
REACTIONS
.
261
5.4.1
1,2
ANIONIC
REARRANGEMENTS;
LONE-PAIR
INVERSION
.
.
.
261
5.4.2
TRIPLET
CARBENES
AND
NITRENES
.
262
5.5
SUMMARY
.
264
PROBLEMS
.
264
6
TRANSITION-METAL-MEDIATED
AND
-CATALYZED
REACTIONS
270
6.1
INTRODUCTION
TO
THE
CHEMISTRY
OF
TRANSITION
METALS
.
270
6.1.1
CONVENTIONS
OF
DRAWING
STRUCTURES
.
270
6.1.2
COUNTING
ELECTRONS
.
271
6.1.3
TYPICAL
REACTIONS
.
276
6.1.4
STOICHIOMETRIC
VS.
CATALYTIC
MECHANISMS
.
282
6.2
ADDITION
REACTIONS
.
283
6.2.1
LATE-METAL-CATALYZED
HYDROGENATION
AND
HYDROMETALLATION
(PD,
PT,
RH)
.
283
6.2.2
HYDROFORMYLATION
(CO,
RH)
.
286
XVI
CONTENTS
6.2.3
HYDROZIRCONATION
(ZR)
.
287
6.2.4
ALKENE
POLYMERIZATION
(TI,
ZR,
SC,
AND
OTHERS)
.
288
6.2.5
CYCLOPROPANATION,
EPOXIDATION,
AND
AZIRIDINATION
OF
ALKENES
(CU,
RH,
MN,
TI)
.
290
6.2.6
DIHYDROXYLATION
AND
AMINOHYDROXYLATION
OF
ALKENES
(OS)
.
292
6.2.7
NUCLEOPHILIC
ADDITION
TO
ALKENES
AND
ALKYNES
(HG,
PD)
.
294
6.2.8
CONJUGATE
ADDITION
REACTIONS
(CU)
.
297
6.2.9
REDUCTIVE
COUPLING
REACTIONS
(TI,
ZR)
.
297
6.2.10
PAUSON-KHAND
REACTION
(CO)
.
301
6.2.11
DBTZ
REACTION
(CR)
.
303
6.2.12
METAL-CATALYZED
CYCLOADDITION
AND
CYCLOTRIMERIZATION
(CO,
NI,
RH)
.
306
6.3
SUBSTITUTION
REACTIONS
.
309
6.3.1
HYDROGENOLYSIS
(PD)
.
309
6.3.2
CARBONYLATION
OF
ALKYL
HALIDES
(PD,
RH)
.
311
6.3.3
HECK
REACTION
(PD)
.
313
6.3.4
COUPLING
REACTIONS
BETWEEN
NUCLEOPHILES
AND
C(SP
2
)-X:
KUMADA,
STILLE,
SUZUKI,
NEGISHI,
BUCHWALD-HARTWIG,
SONOGASHIRA,
AND
ULLMANN
REACTIONS
(NI,
PD,
CU)
.
314
6.3.5
ALLYLIC
SUBSTITUTION
(PD)
.
318
6.3.6
PD-CATALYZED
NUCLEOPHILIC
SUBSTITUTION
OF
ALKENES;
WACKER
OXIDATION
.
319
6.3.7
TEBBE
REACTION
(TI)
.
321
6.3.8
PROPARGYL
SUBSTITUTION
IN
CO-ALKYNE
COMPLEXES
.
.
.
322
6.4
REARRANGEMENT
REACTIONS
.
323
6.4.1
ALKENE
ISOMERIZATION
(RH)
.
323
6.4.2
OLEFIN
AND
ALKYNE
METATHESIS
(RU,
W,
MO,
TI)
.
323
6.5
ELIMINATION
REACTIONS
.
326
6.5.1
OXIDATION
OF
ALCOHOLS
(CR,
RU)
.
326
6.5.2
DECARBONYLATION
OF
ALDEHYDES
(RH)
.
326
6.6
SUMMARY
.
327
PROBLEMS
.
328
7
MIXED-MECHANISM
PROBLEMS
334
A
FINAL
WORD
339
INDEX
341 |
| any_adam_object | 1 |
| author | Grossman, Robert B. |
| author_facet | Grossman, Robert B. |
| author_role | aut |
| author_sort | Grossman, Robert B. |
| author_variant | r b g rb rbg |
| building | Verbundindex |
| bvnumber | BV016881383 |
| callnumber-first | Q - Science |
| callnumber-label | QD502 |
| callnumber-raw | QD502.5 |
| callnumber-search | QD502.5 |
| callnumber-sort | QD 3502.5 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 6000 |
| classification_tum | CHE 608f |
| ctrlnum | (OCoLC)300198492 (DE-599)BVBBV016881383 |
| dewey-full | 547/.139 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547/.139 |
| dewey-search | 547/.139 |
| dewey-sort | 3547 3139 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| edition | 2. ed. |
| format | Book |
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| genre | 1\p (DE-588)4151278-9 Einführung gnd-content 2\p (DE-588)4123623-3 Lehrbuch gnd-content Matériel didactique |
| genre_facet | Einführung Lehrbuch Matériel didactique |
| id | DE-604.BV016881383 |
| illustrated | Illustrated |
| indexdate | 2024-08-24T00:18:54Z |
| institution | BVB |
| isbn | 0387954686 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-010241452 |
| oclc_num | 300198492 |
| open_access_boolean | |
| owner | DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-11 DE-188 |
| owner_facet | DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-11 DE-188 |
| physical | XVI, 355 S. graph. Darst. : 25 cm |
| publishDate | 2003 |
| publishDateSearch | 2003 |
| publishDateSort | 2003 |
| publisher | Springer |
| record_format | marc |
| spelling | Grossman, Robert B. Verfasser aut The art of writing reasonable organic reaction mechanisms Robert B. Grossman 2. ed. New York [u.a.] Springer 2003 XVI, 355 S. graph. Darst. : 25 cm txt rdacontent n rdamedia nc rdacarrier Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. (Midwest). Réactions chimiques organiques - Mécanismes ram Réactions organiques (Chimie) Organic reaction mechanisms Reaktionsmechanismus (DE-588)4177123-0 gnd rswk-swf Chemische Reaktion (DE-588)4009853-9 gnd rswk-swf Organische Chemie (DE-588)4043793-0 gnd rswk-swf 1\p (DE-588)4151278-9 Einführung gnd-content 2\p (DE-588)4123623-3 Lehrbuch gnd-content Matériel didactique Organische Chemie (DE-588)4043793-0 s Chemische Reaktion (DE-588)4009853-9 s Reaktionsmechanismus (DE-588)4177123-0 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010241452&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 2\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Grossman, Robert B. The art of writing reasonable organic reaction mechanisms Réactions chimiques organiques - Mécanismes ram Réactions organiques (Chimie) Organic reaction mechanisms Reaktionsmechanismus (DE-588)4177123-0 gnd Chemische Reaktion (DE-588)4009853-9 gnd Organische Chemie (DE-588)4043793-0 gnd |
| subject_GND | (DE-588)4177123-0 (DE-588)4009853-9 (DE-588)4043793-0 (DE-588)4151278-9 (DE-588)4123623-3 |
| title | The art of writing reasonable organic reaction mechanisms |
| title_auth | The art of writing reasonable organic reaction mechanisms |
| title_exact_search | The art of writing reasonable organic reaction mechanisms |
| title_full | The art of writing reasonable organic reaction mechanisms Robert B. Grossman |
| title_fullStr | The art of writing reasonable organic reaction mechanisms Robert B. Grossman |
| title_full_unstemmed | The art of writing reasonable organic reaction mechanisms Robert B. Grossman |
| title_short | The art of writing reasonable organic reaction mechanisms |
| title_sort | the art of writing reasonable organic reaction mechanisms |
| topic | Réactions chimiques organiques - Mécanismes ram Réactions organiques (Chimie) Organic reaction mechanisms Reaktionsmechanismus (DE-588)4177123-0 gnd Chemische Reaktion (DE-588)4009853-9 gnd Organische Chemie (DE-588)4043793-0 gnd |
| topic_facet | Réactions chimiques organiques - Mécanismes Réactions organiques (Chimie) Organic reaction mechanisms Reaktionsmechanismus Chemische Reaktion Organische Chemie Einführung Lehrbuch Matériel didactique |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010241452&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT grossmanrobertb theartofwritingreasonableorganicreactionmechanisms |