, CONTENTS
Preface v
To the Student vii
CHAPTER 1 CHEMICAL BONDING 1
CHAPTER 2 ALKANES 25
CHAPTER 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES 46
CHAPTER 4 ALCOHOLS AND ALKYL HALIDES 67
CHAPTER 5 STRUCTURE AND PREPARATION OF ALKENES:
ELIMINATION REACTIONS 90
CHAPTER 6 REACTIONS OF ALKENES: ADDITION REACTIONS 124
CHAPTER 7 STEREOCHEMISTRY 156
CHAPTER 8 NUCLEOPHILIC SUBSTITUTION 184
CHAPTER 9 ALKYNES 209
CHAPTER 10 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS 230
CHAPTER 11 ARENES AND AROMATICITY 253
CHAPTER 12 REACTIONS OF ARENES:
ELECTROPHILIC AROMATIC SUBSTITUTION 279
iii
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,iv CONTENTS
CHAPTER 13 SPECTROSCOPY 320
CHAPTER 14 ORGANOMETALLIC COMPOUNDS 342
CHAPTER 15 ALCOHOLS, DIOLS, AND THIOLS 364
CHAPTER 16 ETHERS, EPOXIDES, AND SULFIDES 401
CHAPTER 17 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION
TO THE CARBONYL GROUP 426
CHAPTER 18 ENOLS AND ENOLATES 470
CHAPTER 19 CARBOXYLIC ACIDS 502
CHAPTER 20 CARBOXYLIC ACID DERIVATIVES:
NUCLEOPHILIC ACYL SUBSTITUTION 536
CHAPTER 21 ESTER ENOLATES 576
CHAPTER 22 AMINES 604
CHAPTER 23 ARYL HALIDES 656
CHAPTER 24 PHENOLS 676
CHAPTER 25 CARBOHYDRATES 701
CHAPTER 26 LIPIDS 731
CHAPTER 27 AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS 752
APPENDIX A ANSWERS TO THE SELF-TESTS 775
APPENDIX B TABLES 821
B-1 Bond Dissociation Energies of Some Representative Compounds 821
B-2 Acid Dissociation Constants 822
B-3 Chemical Shifts of Representative Types of Protons 822
B-4 Chemical Shifts of Representative Carbons 823
B-5 Infrared Absorption Frequencies of Some Common Structural Units 823
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, CHAPTER 1
CHEMICAL BONDING
SOLUTIONS TO TEXT PROBLEMS
1.1 The element carbon has atomic number 6, and so it has a total of six electrons. Two of these elec-
trons are in the 1s level. The four electrons in the 2s and 2p levels (the valence shell) are the valence
electrons. Carbon has four valence electrons.
1.2 Electron configurations of elements are derived by applying the following principles:
(a) The number of electrons in a neutral atom is equal to its atomic number Z.
(b) The maximum number of electrons in any orbital is 2.
(c) Electrons are added to orbitals in order of increasing energy, filling the 1s orbital before any
electrons occupy the 2s level. The 2s orbital is filled before any of the 2p orbitals, and the
3s orbital is filled before any of the 3p orbitals.
(d) All the 2p orbitals (2px, 2py, 2pz) are of equal energy, and each is singly occupied before any
is doubly occupied. The same holds for the 3p orbitals.
With this as background, the electron configuration of the third-row elements is derived as
follows [2p6 2px22py22pz2]:
Na (Z 11) 1s22s22p63s1
Mg (Z 12) 1s22s22p63s2
Al (Z 13) 1s22s22p63s23px1
Si (Z 14) 1s22s22p63s23px13py1
P (Z 15) 1s22s22p63s23px13py13pz1
S (Z 16) 1s22s22p63s23px23py13pz1
Cl (Z 17) 1s22s22p63s23px23py23pz1
Ar (Z 18) 1s22s22p63s23px23py23pz2
1
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Preface v
To the Student vii
CHAPTER 1 CHEMICAL BONDING 1
CHAPTER 2 ALKANES 25
CHAPTER 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES 46
CHAPTER 4 ALCOHOLS AND ALKYL HALIDES 67
CHAPTER 5 STRUCTURE AND PREPARATION OF ALKENES:
ELIMINATION REACTIONS 90
CHAPTER 6 REACTIONS OF ALKENES: ADDITION REACTIONS 124
CHAPTER 7 STEREOCHEMISTRY 156
CHAPTER 8 NUCLEOPHILIC SUBSTITUTION 184
CHAPTER 9 ALKYNES 209
CHAPTER 10 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS 230
CHAPTER 11 ARENES AND AROMATICITY 253
CHAPTER 12 REACTIONS OF ARENES:
ELECTROPHILIC AROMATIC SUBSTITUTION 279
iii
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,iv CONTENTS
CHAPTER 13 SPECTROSCOPY 320
CHAPTER 14 ORGANOMETALLIC COMPOUNDS 342
CHAPTER 15 ALCOHOLS, DIOLS, AND THIOLS 364
CHAPTER 16 ETHERS, EPOXIDES, AND SULFIDES 401
CHAPTER 17 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION
TO THE CARBONYL GROUP 426
CHAPTER 18 ENOLS AND ENOLATES 470
CHAPTER 19 CARBOXYLIC ACIDS 502
CHAPTER 20 CARBOXYLIC ACID DERIVATIVES:
NUCLEOPHILIC ACYL SUBSTITUTION 536
CHAPTER 21 ESTER ENOLATES 576
CHAPTER 22 AMINES 604
CHAPTER 23 ARYL HALIDES 656
CHAPTER 24 PHENOLS 676
CHAPTER 25 CARBOHYDRATES 701
CHAPTER 26 LIPIDS 731
CHAPTER 27 AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS 752
APPENDIX A ANSWERS TO THE SELF-TESTS 775
APPENDIX B TABLES 821
B-1 Bond Dissociation Energies of Some Representative Compounds 821
B-2 Acid Dissociation Constants 822
B-3 Chemical Shifts of Representative Types of Protons 822
B-4 Chemical Shifts of Representative Carbons 823
B-5 Infrared Absorption Frequencies of Some Common Structural Units 823
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, CHAPTER 1
CHEMICAL BONDING
SOLUTIONS TO TEXT PROBLEMS
1.1 The element carbon has atomic number 6, and so it has a total of six electrons. Two of these elec-
trons are in the 1s level. The four electrons in the 2s and 2p levels (the valence shell) are the valence
electrons. Carbon has four valence electrons.
1.2 Electron configurations of elements are derived by applying the following principles:
(a) The number of electrons in a neutral atom is equal to its atomic number Z.
(b) The maximum number of electrons in any orbital is 2.
(c) Electrons are added to orbitals in order of increasing energy, filling the 1s orbital before any
electrons occupy the 2s level. The 2s orbital is filled before any of the 2p orbitals, and the
3s orbital is filled before any of the 3p orbitals.
(d) All the 2p orbitals (2px, 2py, 2pz) are of equal energy, and each is singly occupied before any
is doubly occupied. The same holds for the 3p orbitals.
With this as background, the electron configuration of the third-row elements is derived as
follows [2p6 2px22py22pz2]:
Na (Z 11) 1s22s22p63s1
Mg (Z 12) 1s22s22p63s2
Al (Z 13) 1s22s22p63s23px1
Si (Z 14) 1s22s22p63s23px13py1
P (Z 15) 1s22s22p63s23px13py13pz1
S (Z 16) 1s22s22p63s23px23py13pz1
Cl (Z 17) 1s22s22p63s23px23py23pz1
Ar (Z 18) 1s22s22p63s23px23py23pz2
1
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