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, Study Guide and Student Solutions ManualOrganic Chemistry
EIGHTH EDITION
John McMurry
Prepared by
Susan McMurry
Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
,Contents
Solutions to Problems
Chapter 1 Structure and Bonding 1
Chapter 2 Polar Covalent Bonds; Acids and Bases 20
Review Unit 1 38
Chapter 3 Organic Compounds: Alkanes and Their Stereochemistry 41
Chapter 4 Organic Compounds Cycloalkanes and Their Stereochemistry 64
Chapter 5 Stereochemistry 88
Review Unit 2 112
Chapter 6 An Overview of Organic Reactions 116
Chapter 7 Alkenes: Structure and Reactivity 132
Chapter 8 Alkenes: Reactions and Synthesis 158
Review Unit 3 186
Chapter 9 Alkynes: An Introduction to Organic Synthesis 190
Chapter 10 Organohalides 213
Chapter 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 233
Review Unit 4 264
Chapter 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy 268
Chapter 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 289
Review Unit 5 316
Chapter 14 Conjugated Dienes and Ultraviolet Spectroscopy 319
Chapter 15 Benzene and Aromaticity 342
Chapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution 361
Review Unit 6 400
Chapter 17 Alcohols and Phenols 404
Chapter 18 Ethers and Epoxides; Thiols and Sulfides 440
Review Unit 7 469
Carbonyl Preview 472
Chapter 19 Aldehydes and Ketones: Nucleophilic Addition Reactions 474
Chapter 20 Carboxylic Acids and Nitriles 518
Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 544
Review Unit 8 584
Chapter 22 Carbonyl Alpha-Substitution Reactions 588
Chapter 23 Carbonyl Condensation Reactions 616
Chapter 24 Amines and Heterocycles 654
Review Unit 9 698
Chapter 25 Biomolecules: Carbohydrates 701
Chapter 26 Biomolecules: Amino Acids, Peptides, and Proteins 733
Review Unit 10 762
Chapter 27 Biomolecules: Lipids 765
Chapter 28 Biomolecules: Nucleic Acids 790
Chapter 29 The Organic Chemistry of Metabolic Pathways 807
Review Unit 11 832
Chapter 30 Orbitals and Organic Chemistry: Pericyclic Reactions 836
Chapter 31 Synthetic Polymers 857
Review Unit 12 874
Appendices
Functional-Group Synthesis 877
Functional-Group Reactions 882
Reagents in Organic Chemistry 886
Name Reactions in Organic Chemistry 893
Abbreviations 901
Infrared Absorption Frequencies 904
Proton NMR Chemical Shifts 907
Nobel Prize Winners in Chemistry 908
Answers to Review-Unit Questions 917
iii
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
, Chapter 1 – Structure and Bonding
Chapter Outline
I. Atomic Structure (Sections 1.1–1.3).
A. Introduction to atomic structure (Section 1.1).
1. An atom consists of a dense, positively charged nucleus surrounded by negatively
charged electrons.
a. The nucleus is made up of positively charged protons and uncharged neutrons.
b. The nucleus contains most of the mass of the atom.
c. Electrons move about the nucleus at a distance of about 2 x 10–10 m (200 pm).
2. The atomic number (Z) gives the number of protons in the nucleus.
3. The mass number (A) gives the total number of protons and neutrons.
4. All atoms of a given element have the same value of Z.
a. Atoms of a given element can have different values of A.
b. Atoms of the same element with different values of A are called isotopes.
B. Orbitals (Section 1.2).
1. The distribution of electrons in an atom can be described by a wave equation.
a. The solution to a wave equation is an orbital, represented by Ψ.
b. Ψ2 predicts the volume of space in which an electron is likely to be found.
2. There are four different kinds of orbitals (s, p, d, f).
a. The s orbitals are spherical.
b. The p orbitals are dumbbell-shaped.
c. Four of the five d orbitals are cloverleaf-shaped.
3. An atom's electrons are organized into electron shells.
a. The shells differ in the numbers and kinds of orbitals they contain.
b. Electrons in different orbitals have different energies.
c. Each orbital can hold up to a maximum of two electrons.
4. The two lowest-energy electrons are in the 1s orbital.
a. The 2s orbital is the next higher in energy.
b. The next three orbitals are 2px, 2py and 2pz, which have the same energy.
i. Each p orbital has a region of zero density, called a node.
c. The lobes of a p orbital have opposite algebraic signs.
C. Electron Configuration (Section 1.3).
1. The ground-state electron configuration of an atom is a listing of the orbitals
occupied by the electrons of the atom in the lowest energy configuration.
2. Rules for predicting the ground-state electron configuration of an atom:
a. Orbitals with the lowest energy levels are filled first.
i. The order of filling is 1s, 2s, 2p, 3s, 3p, 4s, 3d.
b. Only two electrons can occupy each orbital, and they must be of opposite spin.
c. If two or more orbitals have the same energy, one electron occupies each until
all are half-full (Hund's rule). Only then does a second electron occupy one of
the orbitals.
i. All of the electrons in half-filled shells have the same spin.
II. Chemical Bonding Theory (Sections 1.4–1.5).
A. Development of chemical bonding theory (Section 1.4).
1. Kekulé and Couper proposed that carbon has four "affinity units"; carbon is
tetravalent.
2. Kekulé suggested that carbon can form rings and chains.
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
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