SOLUTION MANUAL FOR
Organic Chemistry
by Leroy Wade, Jan Simek
9th Edition
, LUT MANUAL
Jan William Simek
California Polytechnic State University
OR C
9th EDITION
L. G. Wade, Jr.
iii
,Preface...................................................................................................................................................................................................... V
Symbols And Abbreviations ....................................................................................................................................................... Vii
Chapter 1 Introduction And Review ...............................................................................................................................1
Chapter 2 Structure And Properties Of Organic Molecules ......................................................................... 25
Chapter 3 Structure And Stereochemistry Of Alkanes ................................................................................... 45
Chapter 4 The Study Of Chemical Reactions ...................................................................................................... 59
Chapter 5 Stereochemistry ............................................................................................................................................... 79
Chapter 6 Alkyl Halides: Nucleophilic Substitution And Elimination................................................ 99
Chapter 7 Structure And Synthesis Of Alkenes ................................................................................................. 135
Chapter 8 Reactions Of Alkenes ............................................................................................................................... 159
Chapter 9 Alkynes .............................................................................................................................................................. 191
Chapter 10 Structure And Synthesis Of Alcohols ................................................................................................ 211
Chapter 11 Reactions Of Alcohols ..............................................................................................................................229
Chapter 12 Infrared Spectroscopy And Mass Spectrometry......................................................................... 259
Chapter 13 Nuclear Magnetic Resonance Spectroscopy ................................................................................ 271
Chapter 14 Ethers, Epoxides, And Sulfides ........................................................................................................... 299
Chapter 15 Conjugated Systems, Orbital Symmetry, And Ultraviolet Spectroscopy.................... 317
Chapter 16 Aromatic Compounds .............................................................................................................................. 341
Chapter 17 Reactions Of Aromatic Compounds .................................................................................................365
Chapter 18 Ketones And Aldehydes........................................................................................................................... 401
Chapter 19 Amines ............................................................................................................................................................... 439
Chapter 20 Carboxylic Acids ........................................................................................................................................ 469
Chapter 21 Carboxylic Acid Derivatives ................................................................................................................ 499
Chapter 22 Condensations And Alpha Substitutions Of Carbonyl Compounds ................................ 537
Chapter 23 Carbohydrates And Nucleic Acids .....................................................................................................585
Chapter 24 Amino Acids, Peptides, And Proteins ............................................................................................. 617
Chapter 25 Lipids ...................................................................................................................................................................645
Chapter 26 Synthetic Polymers ...................................................................................................................................... 659
Appendix I: Summary Of IUPAC Nomenclature ................................................................................................ 675
Appendix 2: Summary Of Acidity And Basicity ................................................................................................... 689
iii
, SYMBOLS AND ABBREVIATIONS
b elow i s a list ofsymb OLs A n d abbreviati o Ns u s d in this sol utions manua l, co Nsi stent w I ththo s used In
T h e text b oo k b y w ade . ( d o not expec t all of these to m ake sen se to y o u n o W . y o u w il l le rna th em
throughout your study of organic chemistry.)
BONDS
A Single Bond
A Double Bond
A Triple Bond
- A Bond In Three Dimensions, Coming Out Of The Paper Toward The Reader
111111111111
A Bond In Three Dimensions, Going Behind The Paper Away From The
Reader A Stretched Bond, In The Process Of Forming Or Breaking
ARROWS
- In A Reaction, Shows Direction From Reactants To Products
Signifies Equilibrium (Not To Be Confused With Resonance)
Signifies Resonance (Not To Be Confused With Equilibrium)
Shows Direction Of Electron Movement:
the arrowhead with one barb shows movement of one electron;
The Arrowhead With Two Barbs Shows Movement Of A Pair Of Electrons
S h o w s Polarity Of A Bond Or Molecule, The Arrowhead Signifying The More Negative End Of The
d ip o le
SUBSTITUENT GROUPS
Me A Methyl Group, CH3
Et An Ethyl Group, CH2CH3
Pr A Propyl Group, A Three Carbon Group (Two Possible Arrangements)
Bu A Butyl Group, A Four Carbon Group (Four Possible Arrangements)
R The General Abbreviation For An Alkyl Group (Or Any Substituent Group Not Under
Scrutiny) Ph A Phenyl Group, The Name Of A Benzene Ring As A Substituent, Represented:
Ar The General Name For An Aromatic
Or
0-
Group Continued On Next Page
iv
Organic Chemistry
by Leroy Wade, Jan Simek
9th Edition
, LUT MANUAL
Jan William Simek
California Polytechnic State University
OR C
9th EDITION
L. G. Wade, Jr.
iii
,Preface...................................................................................................................................................................................................... V
Symbols And Abbreviations ....................................................................................................................................................... Vii
Chapter 1 Introduction And Review ...............................................................................................................................1
Chapter 2 Structure And Properties Of Organic Molecules ......................................................................... 25
Chapter 3 Structure And Stereochemistry Of Alkanes ................................................................................... 45
Chapter 4 The Study Of Chemical Reactions ...................................................................................................... 59
Chapter 5 Stereochemistry ............................................................................................................................................... 79
Chapter 6 Alkyl Halides: Nucleophilic Substitution And Elimination................................................ 99
Chapter 7 Structure And Synthesis Of Alkenes ................................................................................................. 135
Chapter 8 Reactions Of Alkenes ............................................................................................................................... 159
Chapter 9 Alkynes .............................................................................................................................................................. 191
Chapter 10 Structure And Synthesis Of Alcohols ................................................................................................ 211
Chapter 11 Reactions Of Alcohols ..............................................................................................................................229
Chapter 12 Infrared Spectroscopy And Mass Spectrometry......................................................................... 259
Chapter 13 Nuclear Magnetic Resonance Spectroscopy ................................................................................ 271
Chapter 14 Ethers, Epoxides, And Sulfides ........................................................................................................... 299
Chapter 15 Conjugated Systems, Orbital Symmetry, And Ultraviolet Spectroscopy.................... 317
Chapter 16 Aromatic Compounds .............................................................................................................................. 341
Chapter 17 Reactions Of Aromatic Compounds .................................................................................................365
Chapter 18 Ketones And Aldehydes........................................................................................................................... 401
Chapter 19 Amines ............................................................................................................................................................... 439
Chapter 20 Carboxylic Acids ........................................................................................................................................ 469
Chapter 21 Carboxylic Acid Derivatives ................................................................................................................ 499
Chapter 22 Condensations And Alpha Substitutions Of Carbonyl Compounds ................................ 537
Chapter 23 Carbohydrates And Nucleic Acids .....................................................................................................585
Chapter 24 Amino Acids, Peptides, And Proteins ............................................................................................. 617
Chapter 25 Lipids ...................................................................................................................................................................645
Chapter 26 Synthetic Polymers ...................................................................................................................................... 659
Appendix I: Summary Of IUPAC Nomenclature ................................................................................................ 675
Appendix 2: Summary Of Acidity And Basicity ................................................................................................... 689
iii
, SYMBOLS AND ABBREVIATIONS
b elow i s a list ofsymb OLs A n d abbreviati o Ns u s d in this sol utions manua l, co Nsi stent w I ththo s used In
T h e text b oo k b y w ade . ( d o not expec t all of these to m ake sen se to y o u n o W . y o u w il l le rna th em
throughout your study of organic chemistry.)
BONDS
A Single Bond
A Double Bond
A Triple Bond
- A Bond In Three Dimensions, Coming Out Of The Paper Toward The Reader
111111111111
A Bond In Three Dimensions, Going Behind The Paper Away From The
Reader A Stretched Bond, In The Process Of Forming Or Breaking
ARROWS
- In A Reaction, Shows Direction From Reactants To Products
Signifies Equilibrium (Not To Be Confused With Resonance)
Signifies Resonance (Not To Be Confused With Equilibrium)
Shows Direction Of Electron Movement:
the arrowhead with one barb shows movement of one electron;
The Arrowhead With Two Barbs Shows Movement Of A Pair Of Electrons
S h o w s Polarity Of A Bond Or Molecule, The Arrowhead Signifying The More Negative End Of The
d ip o le
SUBSTITUENT GROUPS
Me A Methyl Group, CH3
Et An Ethyl Group, CH2CH3
Pr A Propyl Group, A Three Carbon Group (Two Possible Arrangements)
Bu A Butyl Group, A Four Carbon Group (Four Possible Arrangements)
R The General Abbreviation For An Alkyl Group (Or Any Substituent Group Not Under
Scrutiny) Ph A Phenyl Group, The Name Of A Benzene Ring As A Substituent, Represented:
Ar The General Name For An Aromatic
Or
0-
Group Continued On Next Page
iv
