Study Guide and Solutions Manual
Organic Chemistry
A Short Course
THIRTEENTH EDITION
David J. Hart
The Ohio State University
Christopher M. Hadad
The Ohio State University
Leslie E. Craine
Central Connecticut State University
Harold Hart
Michigan State University
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These require
students
Prepared by
David J. Hart
The Ohio State University
Christopher M. Hadad
The Ohio State University
Leslie E. Craine
Central Connecticut State University
Harold Hart
Michigan State University
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.
,Contents
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These
require students
Introduction to the Student ..................................................................................................... v
Chapter 1 Bonding and Isomerism .................................................................................. 1
Chapter 2 Alkanes and Cycloalkanes; Conformational and Geometric Isomerism .......... 19
Chapter 3 Alkenes and Alkynes .................................................................................... 37
Chapter 4 Aromatic Compounds ................................................................................... 61
Chapter 5 Stereoisomerism........................................................................................... 87
Chapter 6 Organic Halogen Compounds; Substitution and Elimination Reactions ........ 109
Chapter 7 Alcohols, Phenols, and Thiols ..................................................................... 123
Chapter 8 Ethers and Epoxides................................................................................... 141
Chapter 9 Aldehydes and Ketones .............................................................................. 157
Chapter 10 Carboxylic Acids and Their Derivatives ....................................................... 187
Chapter 11 Amines and Related Nitrogen Compounds .................................................. 211
Chapter 12 Spectroscopy and Structure Determination ................................................. 233
Chapter 13 Heterocyclic Compounds ............................................................................ 247
Chapter 14 Synthetic Polymers ..................................................................................... 263
Chapter 15 Lipids and Detergents ................................................................................. 279
Chapter 16 Carbohydrates ............................................................................................ 291
Chapter 17 Amino Acids, Peptides, and Proteins........................................................... 317
Chapter 18 Nucleotides and Nucleic Acids .................................................................... 345
Summary of Synthetic Methods ......................................................................................... 361
Summary of Reaction Mechanisms .................................................................................... 375
Review Problems On Synthesis ......................................................................................... 381
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
, Sample Multiple Choice Test Questions ............................................................................. 385
1
Bonding and Isomerism
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These require
students
Chapter Summary
An atom consists of a nucleus surrounded by electrons arranged in orbitals. The electrons
in the outer shell, or the valence electrons, are involved in bonding. Ionic bonds are
formed by electron transfer from an electropositive atom to an electronegative atom.
Atoms with similar electronegativities form covalent bonds by sharing electrons. A single
bond is the sharing of one electron pair between two atoms. A covalent bond has specific
bond length and bond energy.
Carbon, with four valence electrons, mainly forms covalent bonds. It usually forms
four such bonds, and these may be with itself or with other atoms such as hydrogen,
oxygen, nitrogen, chlorine, and sulfur. In pure covalent bonds, electrons are shared equally,
but in polar covalent bonds, the electrons are displaced toward the more electronegative
element. Multiple bonds consist of two or three electron pairs shared between atoms.
Structural (or constitutional) isomers are compounds with the same molecular
formulas but different structural formulas (that is, different arrangements of the atoms in
the molecule). Isomerism is especially important in organic chemistry because of the
capacity of carbon atoms to be arranged in so many different ways: continuous chains,
branched chains, and rings. Structural formulas can be written so that every bond is shown,
or in various abbreviated forms. For example, the formula for n-pentane (n stands for
normal) can be written as:
H H H H H
H C C C C C H or CH3CH2CH2CH2CH3 or
H H H H H
Some atoms, even in covalent compounds, carry a formal charge, defined as the
number of valence electrons in the neutral atom minus the sum of the number of unshared
electrons and half the number of shared electrons. Resonance occurs when we can write
two or more structures for a molecule or ion with the same arrangement of atoms but
different arrangements of the electrons. The correct structure of the molecule or ion is a
resonance hybrid of the contributing structures, which are drawn with a double-headed
arrow () between them. Organic chemists use a curved arrow ( ) to show the movement
of an electron pair.
A sigma () bond is formed between atoms by the overlap of two atomic orbitals
along the line that connects the atoms. Carbon uses sp3-hybridized orbitals to form four
such bonds. These bonds are directed from the carbon nucleus toward the corners of a
tetrahedron. In methane, for example, the carbon is at the center and the four hydrogens
are at the corners of a regular tetrahedron with H–C–H bond angles of 109.5.
In the chapter summaries, terms whose meanings you should know appear in boldface type.
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
, Carbon compounds can be classified according to their molecular framework as
acyclic (not cyclic), carbocyclic (containing rings of carbon atoms), or heterocyclic
(containing at least one ring atom that is not carbon). They may also be classified according
to functional group (Table 1.6).
Learning Objectives
1. Know the meaning of: nucleus, electrons, protons, neutrons, atomic number, atomic
weight, shells, orbitals, valence electrons, valence, kernel.
2. Know the meaning of: electropositive, electronegative, ionic and covalent bonds,
radical, catenation, polar covalent bond, single and multiple bonds, nonbonding or
unshared electron pair, bond length, bond energy.
3. Know the meaning of: molecular formula, structural formula, structural (or
constitutional) isomers, continuous and branched chain, formal charge, resonance,
contributing structures, sigma () bond, sp3-hybrid orbitals, tetrahedral carbon.
4. Know the meaning of: acyclic, carbocyclic, heterocyclic, functional group.
5. Given a periodic table, determine the number of valence electrons of an element and
write its electron-dot formula.
6. Know the meaning of the following symbols:
+ –
7. Given two elements and a periodic table, tell which element is more electropositive
or electronegative.
8. Given the formula of a compound and a periodic table, classify the compound as
ionic or covalent.
9. Given an abbreviated structural formula of a compound, write its electron-dot
formula.
10. Given a covalent bond, tell whether it is polar. If it is, predict the direction of bond
polarity from the electronegativities of the atoms.
11. Given a molecular formula, draw the structural formulas for all possible structural
isomers.
12. Given a structural formula abbreviated on one line of type, write the complete
structure and clearly show the arrangement of atoms in the molecule.
13. Given a line formula, such as (pentane), write the complete structure and
clearly show the arrangement of atoms in the molecule. Tell how many hydrogens
are attached to each carbon, what the molecular formula is, and what the functional
groups are.
14. Given a simple molecular formula, draw the electron-dot formula and determine
whether each atom in the structure carries a formal charge.
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These require
students
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
Organic Chemistry
A Short Course
THIRTEENTH EDITION
David J. Hart
The Ohio State University
Christopher M. Hadad
The Ohio State University
Leslie E. Craine
Central Connecticut State University
Harold Hart
Michigan State University
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These require
students
Prepared by
David J. Hart
The Ohio State University
Christopher M. Hadad
The Ohio State University
Leslie E. Craine
Central Connecticut State University
Harold Hart
Michigan State University
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.
,Contents
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These
require students
Introduction to the Student ..................................................................................................... v
Chapter 1 Bonding and Isomerism .................................................................................. 1
Chapter 2 Alkanes and Cycloalkanes; Conformational and Geometric Isomerism .......... 19
Chapter 3 Alkenes and Alkynes .................................................................................... 37
Chapter 4 Aromatic Compounds ................................................................................... 61
Chapter 5 Stereoisomerism........................................................................................... 87
Chapter 6 Organic Halogen Compounds; Substitution and Elimination Reactions ........ 109
Chapter 7 Alcohols, Phenols, and Thiols ..................................................................... 123
Chapter 8 Ethers and Epoxides................................................................................... 141
Chapter 9 Aldehydes and Ketones .............................................................................. 157
Chapter 10 Carboxylic Acids and Their Derivatives ....................................................... 187
Chapter 11 Amines and Related Nitrogen Compounds .................................................. 211
Chapter 12 Spectroscopy and Structure Determination ................................................. 233
Chapter 13 Heterocyclic Compounds ............................................................................ 247
Chapter 14 Synthetic Polymers ..................................................................................... 263
Chapter 15 Lipids and Detergents ................................................................................. 279
Chapter 16 Carbohydrates ............................................................................................ 291
Chapter 17 Amino Acids, Peptides, and Proteins........................................................... 317
Chapter 18 Nucleotides and Nucleic Acids .................................................................... 345
Summary of Synthetic Methods ......................................................................................... 361
Summary of Reaction Mechanisms .................................................................................... 375
Review Problems On Synthesis ......................................................................................... 381
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
, Sample Multiple Choice Test Questions ............................................................................. 385
1
Bonding and Isomerism
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These require
students
Chapter Summary
An atom consists of a nucleus surrounded by electrons arranged in orbitals. The electrons
in the outer shell, or the valence electrons, are involved in bonding. Ionic bonds are
formed by electron transfer from an electropositive atom to an electronegative atom.
Atoms with similar electronegativities form covalent bonds by sharing electrons. A single
bond is the sharing of one electron pair between two atoms. A covalent bond has specific
bond length and bond energy.
Carbon, with four valence electrons, mainly forms covalent bonds. It usually forms
four such bonds, and these may be with itself or with other atoms such as hydrogen,
oxygen, nitrogen, chlorine, and sulfur. In pure covalent bonds, electrons are shared equally,
but in polar covalent bonds, the electrons are displaced toward the more electronegative
element. Multiple bonds consist of two or three electron pairs shared between atoms.
Structural (or constitutional) isomers are compounds with the same molecular
formulas but different structural formulas (that is, different arrangements of the atoms in
the molecule). Isomerism is especially important in organic chemistry because of the
capacity of carbon atoms to be arranged in so many different ways: continuous chains,
branched chains, and rings. Structural formulas can be written so that every bond is shown,
or in various abbreviated forms. For example, the formula for n-pentane (n stands for
normal) can be written as:
H H H H H
H C C C C C H or CH3CH2CH2CH2CH3 or
H H H H H
Some atoms, even in covalent compounds, carry a formal charge, defined as the
number of valence electrons in the neutral atom minus the sum of the number of unshared
electrons and half the number of shared electrons. Resonance occurs when we can write
two or more structures for a molecule or ion with the same arrangement of atoms but
different arrangements of the electrons. The correct structure of the molecule or ion is a
resonance hybrid of the contributing structures, which are drawn with a double-headed
arrow () between them. Organic chemists use a curved arrow ( ) to show the movement
of an electron pair.
A sigma () bond is formed between atoms by the overlap of two atomic orbitals
along the line that connects the atoms. Carbon uses sp3-hybridized orbitals to form four
such bonds. These bonds are directed from the carbon nucleus toward the corners of a
tetrahedron. In methane, for example, the carbon is at the center and the four hydrogens
are at the corners of a regular tetrahedron with H–C–H bond angles of 109.5.
In the chapter summaries, terms whose meanings you should know appear in boldface type.
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
, Carbon compounds can be classified according to their molecular framework as
acyclic (not cyclic), carbocyclic (containing rings of carbon atoms), or heterocyclic
(containing at least one ring atom that is not carbon). They may also be classified according
to functional group (Table 1.6).
Learning Objectives
1. Know the meaning of: nucleus, electrons, protons, neutrons, atomic number, atomic
weight, shells, orbitals, valence electrons, valence, kernel.
2. Know the meaning of: electropositive, electronegative, ionic and covalent bonds,
radical, catenation, polar covalent bond, single and multiple bonds, nonbonding or
unshared electron pair, bond length, bond energy.
3. Know the meaning of: molecular formula, structural formula, structural (or
constitutional) isomers, continuous and branched chain, formal charge, resonance,
contributing structures, sigma () bond, sp3-hybrid orbitals, tetrahedral carbon.
4. Know the meaning of: acyclic, carbocyclic, heterocyclic, functional group.
5. Given a periodic table, determine the number of valence electrons of an element and
write its electron-dot formula.
6. Know the meaning of the following symbols:
+ –
7. Given two elements and a periodic table, tell which element is more electropositive
or electronegative.
8. Given the formula of a compound and a periodic table, classify the compound as
ionic or covalent.
9. Given an abbreviated structural formula of a compound, write its electron-dot
formula.
10. Given a covalent bond, tell whether it is polar. If it is, predict the direction of bond
polarity from the electronegativities of the atoms.
11. Given a molecular formula, draw the structural formulas for all possible structural
isomers.
12. Given a structural formula abbreviated on one line of type, write the complete
structure and clearly show the arrangement of atoms in the molecule.
13. Given a line formula, such as (pentane), write the complete structure and
clearly show the arrangement of atoms in the molecule. Tell how many hydrogens
are attached to each carbon, what the molecular formula is, and what the functional
groups are.
14. Given a simple molecular formula, draw the electron-dot formula and determine
whether each atom in the structure carries a formal charge.
include:Essay/Problem-Based Questions: In law exams, students are often given hypothetical scenarios (problem questions) and are asked to analyze the legal issues involved. These require
students
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
