Index

acid strength

Acidity Constant

12.4: Alkyne Acidity - Formation of Acetylide Anions

acidity order

activation energy

6.9: Describing a Reaction - Energy Diagrams and Transition States

addition reaction

6.1: Kinds of Organic Reactions

alkanes

3.5: Naming Alkanes

alkene reaction map

12.9: An Introduction to Organic Synthesis

alkyl group

10.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements

Alkyl Shift

alkylation

12.3: Alkylation of Acetylide Anions

alkyne

12.5: Reactions of Alkynes - Addition of HX and X₂
12.8: Oxidative Cleavage of Alkynes

alkynes

12.1: Naming Alkynes

allyl radical

8.5: Stability of the Allyl Radical - Resonance Revisited

Allylic Bromination

8.4: Preparing Alkyl Halides from Alkenes - Allylic Bromination

allylic carbon

8.4: Preparing Alkyl Halides from Alkenes - Allylic Bromination

angle strain

anion radical

12.7: Reduction of Alkynes

anti conformation

4.6: Axial and Equatorial Bonds in Cyclohexane

Aromatic Ions

2.8: Aromatic Ions

Author Bars

10.3: Naming Alkenes

axial position

B

Baeyer theory

base strength

9.6: Characteristics of the SN1 Reaction

benzylic

bimolecular reaction

9.12: Biological Elimination Reactions

biological elimination reactions

bonding molecular orbital

1.2: Describing Chemical Bonds- Molecular Orbital Theory

bridgehead carbon atom

4.9: Conformations of Polycyclic Molecules

C

carbocation

6.5: An Example of a Polar Reaction - Addition of HBr to Ethylene

Carbocation Rearrangements

10.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements

carbocations

1.5: Formal Charges

carbocycles

chain reaction

4.5: Conformations of Cyclohexane

chair conformation

chiral resolution

5.4: Enantiomers and the Tetrahedral Carbon
5.5: The Reason for Handedness in Molecules - Chirality

chirality

conformation

4.8: Conformations of Disubstituted Cyclohexanes

conformational analysis

conjugate acid

7.1: Acids and Bases - The Brønsted-Lowry Definition

conjugate bases

7.1: Acids and Bases - The Brønsted-Lowry Definition

Conjugated Dienes

2.2: Stability of Conjugated Dienes- Molecular Orbital Theory

conjugation

2.2: Stability of Conjugated Dienes- Molecular Orbital Theory

constitutional isomer

4.2: Cis-Trans Isomerism in Cycloalkanes

cycloalkanes

4.1: Naming Cycloalkanes

cyclobutadienyl ring

4.5: Conformations of Cyclohexane

cyclohexane

cyclohexanes

4.7: Conformations of Monosubstituted Cyclohexanes

cyclopentadiene ion

2.8: Aromatic Ions

cyclopentadienyl ring

cyclopropenyl ring

2.6: Structure and Stability of Benzene

D

degenerate

dehydration

11.2: Preparation of Alkenes - A Preview of Elimination Reactions

dehydrohalogenation

11.2: Preparation of Alkenes - A Preview of Elimination Reactions

delocalization

2.3: Resonance

delocalized electrons

8.5: Stability of the Allyl Radical - Resonance Revisited

Deuterium Isotope Effect

9.9: The E2 Reaction and the Deuterium Isotope Effect

dextrorotatory

9.6: Characteristics of the SN1 Reaction

diastereomers

5.7: Diastereomers

dielectric constant

dihedral angle

1.12: Polar Covalent Bonds - Dipole Moments

dipole moment

Disubstituted Cyclohexanes

4.8: Conformations of Disubstituted Cyclohexanes

E

E,Z Notation

10.5: Sequence Rules - The E,Z Designation

E1 reaction

9.11: The E1 and E1cB Reactions

E1cB

9.11: The E1 and E1cB Reactions

E1cB reaction

9.11: The E1 and E1cB Reactions

9.9: The E2 Reaction and the Deuterium Isotope Effect

E2 reaction

9.9: The E2 Reaction and the Deuterium Isotope Effect

eclipsed conformation

3.6: Conformations of Ethane
3.7: Conformations of Other Alkanes

eclipsing strain

6.4: Polar Reactions
7.5: Acids and Bases - The Lewis Definition

electrophile

electrophilic addition

6.5: An Example of a Polar Reaction - Addition of HBr to Ethylene

electrophlic

6.6: Using Curved Arrows in Polar Reaction Mechanisms

elimination reaction

6.1: Kinds of Organic Reactions
11.2: Preparation of Alkenes - A Preview of Elimination Reactions

enantiomer

5.4: Enantiomers and the Tetrahedral Carbon

enantiomeric excess

enantiotopic

4.6: Axial and Equatorial Bonds in Cyclohexane

enol

12.6: Hydration of Alkynes

equatorial position

equilibrium constant

1.8: sp³ Hybrid Orbitals and the Structure of Ethane

ethane

ethylene

1.8: sp³ Hybrid Orbitals and the Structure of Ethane

F

formal charge

1.5: Formal Charges

freon

8.1: Introduction to Organohalides

G

gasoline

gauche conformation

H

Hückel's rule

10.10: The Hammond Postulate

Hammond Postulate

heat of combustion

heteroatom

heterocycles

heterogenic

heterolytic

homogenic

homolytic

1.7: sp³ Hybrid Orbitals and the Structure of Methane

hybrid orbitals

Hydride shift

10.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements

I

initiation step

isobutyl group

isopropyl group

K

kinetics

9.4: Characteristics of the SN2 Reaction

L

leaving group

levorotatory

10.8: Orientation of Electrophilic Additions - Markovnikov's Rule

Lindlar catalyst

12.7: Reduction of Alkynes

M

Markovnikov’s rule

Markovnikov's Rule

10.8: Orientation of Electrophilic Additions - Markovnikov's Rule

mechanism

Meso Compounds

5.8: Meso Compounds

methyl group

1.2: Describing Chemical Bonds- Molecular Orbital Theory

molecular orbital theory

N

Newman projection

6.4: Polar Reactions
7.5: Acids and Bases - The Lewis Definition

nucleophile

nucleophlic

6.6: Using Curved Arrows in Polar Reaction Mechanisms

O

octane scale

optical activity

8: Organohalides- Radical Halogenation of Alkanes and Alkenes

organohalides

oxidation

12.8: Oxidative Cleavage of Alkynes

oxidative cleavage of alkynes

oxymercuration

11.5: Hydration of Alkenes - Addition of H₂O by Oxymercuration

P

PAH

2.10: Polycyclic Aromatic Compounds

periplanar

9.9: The E2 Reaction and the Deuterium Isotope Effect

petroleum

9.2: The Discovery of Nucleophilic Substitution Reactions

phosphorus pentachloride

pKa

7.3: Predicting Acid-Base Reactions from pKa Values

polar aprotic solvent

9.4: Characteristics of the SN2 Reaction

polar covalent bonds

1.12: Polar Covalent Bonds - Dipole Moments

polar reaction

6.2: How Organic Reactions Occur - Mechanisms
6.4: Polar Reactions

polarizability

6.4: Polar Reactions

polarizer

2.10: Polycyclic Aromatic Compounds

polycyclic aromatic compounds

polycyclic aromatic hydrocarbons

2.10: Polycyclic Aromatic Compounds

polycyclic compounds

4.1: Naming Cycloalkanes

polycyclic molecules

4.9: Conformations of Polycyclic Molecules

primary carbon

prochiral

Prochirality

propagation step

Pyridine

pyrimidine

Pyrrole

Q

quaternary carbon

5.9: Racemic Mixtures and the Resolution of Enantiomers

R

racemic mixture

racemization

radical reaction

radical substitution

rate coefficient

rate equation

6.9: Describing a Reaction - Energy Diagrams and Transition States

reaction energy diagram

reaction intermediate

6.10: Describing a Reaction- Intermediates

reaction mechanism

reaction rate

6.1: Kinds of Organic Reactions

rearrangement reaction

Redox Reactions (Organic Chemistry)

reduction

10.8: Orientation of Electrophilic Additions - Markovnikov's Rule

regioselective

regiospecific

10.8: Orientation of Electrophilic Additions - Markovnikov's Rule

resolution

5.2: Optical Activity
5.9: Racemic Mixtures and the Resolution of Enantiomers

Resolution of Enantiomers

5.9: Racemic Mixtures and the Resolution of Enantiomers

resonance contributors

2.4: Rules for Resonance Forms

resonance forms

2.3: Resonance
8.5: Stability of the Allyl Radical - Resonance Revisited

resonance hybrid

2.5: Drawing Resonance Forms
8.5: Stability of the Allyl Radical - Resonance Revisited

resonance hybride

2.4: Rules for Resonance Forms

resonance structure

2.5: Drawing Resonance Forms

retrosynthetic analysis

12.9: An Introduction to Organic Synthesis

ring flip

4.6: Axial and Equatorial Bonds in Cyclohexane

ring strain

S

secondary carbon

10.5: Sequence Rules - The E,Z Designation

sequence rules

SN1

9.5: The SN1 Reaction

SN1 reaction

9.5: The SN1 Reaction

SN2 reaction

9.4: Characteristics of the SN2 Reaction

solvation

sp hybrid orbital

1.10: sp Hybrid Orbitals and the Structure of Acetylene

specific rotation

staggered conformation

4.2: Cis-Trans Isomerism in Cycloalkanes

stereoisomer

steric repulsion

steric strain

strain

strain energy

6.1: Kinds of Organic Reactions

substitution reaction

substitution reactions

2.6: Structure and Stability of Benzene

syn periplanar

9.9: The E2 Reaction and the Deuterium Isotope Effect

T

tautomerism

12.6: Hydration of Alkynes

tautomers

12.6: Hydration of Alkynes

termination step

tertiary carbon

tetraethyl lead