CliffsQuickReview Organic Chemistry II

by Pellegrini, Frank

• ISBN13: 9780764586163
• ISBN10: 0764586165
• Edition: Revised
• Format: Paperback
• Copyright: 2000-07-20
• Publisher: Cliffs Notes

Summary

CliffsQuickReview course guides cover the essentials of your toughest classes. You're sure to get a firm grip on core concepts and key material and be ready for the test with this guide at your side.Whether you're new to biosynthesis, integrated metabolism, and the molecular cloning of DNA or just brushing up on those topics, CliffsQuickReview Organic Chemistry II can help. This guide introduces each topic, defines key terms, and walks you through each sample problem step-by-step. In no time, you'll be ready to tackle other concepts in this book such as The reactions of aromatic compounds Aldol, cross-aldol, and ketonic aldol condensation Ester formation Oxidation Mass spectra CliffsQuickReview Organic Chemistry II acts as a supplement to your textbook and to classroom lectures. Use this reference in any way that fits your personal style for study and review - you decide what works best with your needs. You can either read the book from cover to cover or just look for the information you want and put it back on the shelf for later. What's more, you can Get a glimpse of what you'll gain from a chapter by reading through the introduction at the beginning of each chapter Study your formulas in the Summary of Preparations or the Summary of Reactions Use the glossary to find key terms fast. With titles available for all the most popular high school and college courses, CliffsQuickReview guides are a comprehensive resource that can help you get the best possible grades.

Author Biography

Dr. Frank Pellegrini has been a professor for over 35 years. His field of specialization is heterocyclic organic chemistry. He is the recipient of the State University of New York Chancellor's Award for Excellence in Teaching. Currently he holds the rank of Professor of Organic Chemistry and Department Chair at SUNY Farmingdale. Other interests include photography, travel, and volunteer fire fighting.

Table of Contents

Fundamental Ideas	1	(2)
Aromatic Compounds	3	(14)
Introduction	3	(1)
Benzene	3	(5)
Structure of the benzene molecule	3	(2)
Resonance	5	(2)
Orbital picture of benzene	7	(1)
Huckel's Rule	8	(5)
Nomenclature	9	(3)
Reactions of benzene	12	(1)
Other Aromatic Compounds	13	(2)
Heterocyclic Aromatic Compounds	15	(2)
Reactions of Aromatic Compounds	17	(20)
Electrophilic Aromatic Substitution Reactions	17	(7)
The bromination of benzene	18	(2)
The nitration of benzene	20	(2)
The sulfonation of benzene	22	(2)
The Birch Reduction of Benzene	24	(1)
Friedel-Crafts Alkylation Reaction	25	(3)
Friedel-Crafts Acylation Reaction	28	(2)
Directing Group Influence	30	(3)
Halogen atom influence	31	(1)
Predicting second group position	32	(1)
Theory of Substitution Effects (Directing Group Influence)	33	(4)
Ring Activation	33	(2)
Ring Deactivation	35	(2)
Alkyl Halides	37	(18)
Introduction	37	(2)
Physical properties	37	(1)
Nomenclature	38	(1)
Nucleus and Nucleophiles	39	(1)
Nucleophilic Substitution Reactions	40	(1)
Leaving Group	41	(1)
Mechanisms of Nucleophilic Substitution Reactions	42	(4)
SN2 mechanism	42	(2)
Steric hindrance	44	(1)
Solvent effects	44	(1)
SN1 mechanism	45	(1)
SN1 versus SN2 Reactions	46	(3)
Nature of the carbon skeleton	47	(1)
Nature of the solvent	47	(1)
Nature of the leaving group	48	(1)
Elimination Reactions	49	(1)
Mechanism of Elimination Reactions	50	(2)
E1 mechanism	50	(2)
E2 mechanism	52	(1)
Grignard Reaction	52	(1)
Preparation of Alkyl Halides	52	(3)
Hydrogen halide addition to an alkene	53	(1)
Reaction of alcohols with sulfur and phosphorous halides	54	(1)
Phenols and Aryl Halides	55	(24)
Phenols	55	(3)
Nomenclature	55	(1)
Physical properties	56	(1)
Acidity	57	(1)
Resonance structures of phenol	58	(1)
Synthesis of Phenols	58	(5)
Pyrolysis of sodium benzene sulfonate	59	(1)
Dow process	59	(1)
Air oxidation of cumene	59	(4)
Reactions of Phenolic Hydrogen	63	(2)
Reactions with bases	64	(1)
Esterification of phenol	64	(1)
Williamson ether synthesis	65	(1)
Reactions of Phenolic Benzene Rings	65	(4)
Halogenation	65	(1)
Nitration	66	(1)
Sulfonation	66	(1)
Kolbe reaction	67	(2)
Aryl Halides	69	(1)
Nomenclature	69	(1)
Properties of aryl halides	69	(1)
Synthesis of Aryl Halides	69	(2)
Halogenation of benzene	70	(1)
Sandmeyer reaction	70	(1)
Reactions of Aryl Halides	71	(8)
Grignard reaction	71	(1)
Substitution reaction	72	(1)
SNAR reactions	73	(1)
SNAR mechanism	73	(2)
Elimination-addition reactions	75	(1)
Mechanism for aniline formation	76	(3)
Alcohols and Ethers	79	(24)
Alcohols	79	(2)
Nomenclature	80	(1)
Physical properties	81	(1)
Synthesis of Alcohols	81	(5)
Hydration of alkenes	81	(1)
Reduction of aldehydes and ketones	82	(2)
Reduction of carboxylic acids	84	(1)
Reduction of esters	85	(1)
Grignard reaction with aldehydes and ketones	85	(1)
Reactions of Alcohols	86	(10)
Metal salt formation	86	(1)
Alkyl halide formation	87	(3)
Ester formation	90	(6)
Ethers	96	(3)
Nomenclature	96	(1)
Physical properties	97	(2)
Synthesis of Ethers	99	(2)
Sulfuric acid process	99	(2)
Williamson method	101	(1)
Reactions of Ethers	101	(2)
Aldehydes and Ketones	103	(34)
Aldehydes	103	(2)
Nomenclature	103	(2)
Physical properties	105	(1)
Structure of the carbonyl group	105	(1)
Synthesis of Aldehydes	105	(5)
The oxidation of primary alcohols	106	(1)
The reduction of acyl chlorides, esters, and nitriles	106	(1)
Acyl chloride reduction	106	(2)
Ester and nitrile reduction	108	(1)
Ozonolysis of alkenes	109	(1)
Hydroboration of terminal alkynes	110	(1)
Ketones	110	(2)
Nomenclature	110	(2)
Synthesis of Ketones	112	(2)
Oxidation of secondary alcohols	112	(1)
Hydration of alkynes	112	(1)
Ozonolysis of alkynes	113	(1)
Friedel-Crafts acylation	113	(1)
Lithium dialkylcuprates	113	(1)
Grignard reagents	114	(1)
Reactions of Aldehydes and ketones	114	(23)
Reactions of carbonyl groups	114	(1)
Addition of water	115	(1)
Addition of alcohol	116	(3)
Stability of acetals	119	(1)
Addition of hydrogen cyanide	120	(1)
Addition of ylides (the Wittig reaction)	121	(1)
Addition of organometallic reagents	122	(1)
Addition of ammonia derivatives	122	(3)
Oxidations of aldehydes and ketones	125	(2)
Aldol reactions	127	(1)
Halogenation of ketones	128	(1)
Aldol condensation	129	(1)
Cross-aldol condensation	130	(1)
Ketonic aldol condensation	131	(1)
Cyclizations via aldol condensation	132	(2)
The benzoin condensation	134	(3)
Carboxylic Acids and their Derivatives	137	(34)
Introduction	137	(3)
Nomenclature of carboxylic acids	138	(1)
Naming carboxylic acid salts	139	(1)
Acidity of carboxylic acids	139	(1)
Preparation of Carboxylic Acids	140	(14)
Oxidation of alkenes	140	(1)
Ozonolysis of alkenes	141	(1)
The oxidation of primary alcohols and aldehydes	141	(1)
The oxidation of alkyl benzenes	141	(1)
Hydrolysis of nitriles	142	(3)
The carbonation of Grignard reagents	145	(1)
Synthesis of substituted acetic acids via acetoacetic ester	146	(4)
Synthesis of substituted acetic acid via malonic ester	150	(3)
α halo acids, α hydroxy acids, and α, β unsaturated acids	153	(1)
Reactions of Carboxylic Acids	154	(10)
Ester formation	154	(3)
Nonreversible ester formation	157	(1)
Methyl ester formation	158	(1)
Amide formation	158	(3)
Acid halide formation	161	(1)
Acid anhydride formation	162	(1)
Decarboxylation reaction	163	(1)
Hunsdiecker reaction	164	(1)
Kolbe electrolysis	164	(1)
Reduction of Carboxylic Acids and Acid Derivatives	164	(7)
Reductions of carboxylic acid derivatives	164	(1)
Reduction of esters	165	(1)
Reduction of acid halides	166	(1)
Reduction of amides	166	(1)
Reactions of carboxylic acid derivatives	166	(3)
Reactivity of carboxylic acid derivatives	169	(2)
Amines	171	(16)
Introduction	171	(3)
Classification and nomenclature of amines	171	(2)
Basicity of amines	173	(1)
Preparation of Amines	174	(5)
Alkylation of ammonia	175	(1)
Reduction of alkylazides	175	(1)
Reduction of nitriles	176	(1)
Reduction of amides	176	(1)
Reduction of nitrocompounds	177	(1)
Reductive amination of aldehydes and ketones	178	(1)
Reactions of Amines	179	(8)
Reaction with acids	179	(1)
Reaction with acid halides	179	(1)
Reaction with aldehydes and ketones	179	(1)
Reaction with sulfonyl chlorides	180	(1)
The Hinsberg test	181	(1)
Oxidation	182	(1)
Reaction with nitrous acid	182	(2)
Reactions of aromatic diazonium salts	184	(3)
Spectroscopy and Structure	187	(10)
Introduction	187	(1)
Mass Spectra	187	(2)
Integral molecular weight	187	(2)
Fragment and rearrangement ions	189	(1)
Nuclear Magnetic Resonance (NMR) Spectra	189	(5)
Deshielded and shielded protons	190	(1)
Chemical shifts	191	(1)
Mapping nonequivalent hydrogens	191	(2)
Peak areas	193	(1)
Peak splitting: Spin-spin coupling	193	(1)
Coupling constants	194	(1)
Ultraviolet and Visible Spectra	194	(1)
Infrared Spectra	195	(2)
SUMMARY OF PREPARATIONS	197	(14)
Alkyl Halides	197	(1)
Addition of halogen halide to alkenes	197	(1)
Reaction of phosphorus and sulfur halides with alcohols	197	(1)
Phenols	197	(1)
Pyrolysis of sodium benzene sulfonate	197	(1)
Dow process	198	(1)
Air oxidation of cumene	198	(1)
Aryl Halides	198	(1)
Halogenation of benzene	198	(1)
Sandmeyer reaction	199	(1)
Ethers	199	(1)
Sulfuric acid process	199	(1)
Williamson synthesis	199	(1)
Alcohols	199	(2)
Hydration of alkenes	199	(1)
Hydroboration-oxidation	200	(1)
Reduction of aldehydes and ketones	200	(1)
Reduction of carboxylic acids	200	(1)
Reduction of esters	200	(1)
Grignard reagent with aldehydes and ketones	201	(1)
Aldehydes	201	(1)
Oxidation of primary alcohols	201	(1)
Reduction of acyl halides	201	(1)
Reduction of esters	202	(1)
Reduction of nitriles	202	(1)
Ozonolysis of alkenes	202	(1)
Ketones	202	(2)
Oxidation of secondary alcohols	202	(1)
Hydration of alkynes	203	(1)
Ozonolysis of alkenes	203	(1)
Friedel-Crafts acylation	203	(1)
Via lithium dialkylcuprates	203	(1)
Via a Grignard reagent	204	(1)
Carboxylic Acids	204	(2)
Oxidation of alkenes	204	(1)
Ozonolysis of alkenes	204	(1)
Oxidation of primary alcohols	204	(1)
Oxidation of aldehydes	205	(1)
Oxidation of alkyl benzenes	205	(1)
Hydrolysis of nitriles	205	(1)
Carbonation of a Grignard	205	(1)
Via acetoacetic ester	206	(1)
Halo Acids, α-Hydroxy Acids, and α, β-Unsaturated Acids	206	(1)
Hell-Volhard-Zelinski reaction	206	(1)
Formation of α hydroxy acids	206	(1)
Formation of amino acids	206	(1)
Formation of α, β-unsaturated acids	207	(1)
Amines	207	(4)
Alkylation of ammonia	207	(1)
Via alkylazide reduction	207	(1)
Gabriel synthesis	207	(1)
Reduction of nitriles	208	(1)
Reduction of amides	208	(1)
Reduction of nitrocompounds	208	(1)
Reductive amination of aldehydes and ketones	209	(2)
SUMMARY OF REACTIONS	211	(22)
Aromatic Compounds	211	(2)
Halogenation	211	(1)
Nitration	211	(1)
Sulfonation	211	(1)
Friedel-Crafts alkylation	212	(1)
Friedel-Crafts acylation	212	(1)
Birch reduction	212	(1)
Alkyl Halides	213	(1)
Hydrolysis	213	(1)
Williamson ether synthesis	213	(1)
Nitrile formation	213	(1)
Amine formation	213	(1)
Alkene formation	214	(1)
Grignard formation	214	(1)
Phenols	214	(4)
Neutralization	214	(1)
Ester formation	214	(1)
Ether formation	215	(1)
Halogenation	215	(1)
Nitration	216	(1)
Sulfonation	217	(1)
Kolbe reaction	217	(1)
Aryl Halides	218	(1)
Grignard reaction	218	(1)
Hydrolysis	218	(1)
Amination	218	(1)
Ethers	219	(1)
Cleavage	219	(1)
Protonation	219	(1)
Alcohols	219	(2)
Neutralization	219	(1)
Halide Formation	219	(1)
Ester formation	220	(1)
Oxidation	220	(1)
Carboxylic acid formation	220	(1)
Aldehydes and Ketones	221	(3)
Hydration	221	(1)
Hemiacetal and acetal formation	221	(1)
Hydrogen cyanide addition	221	(1)
Addition of organometallic reagents	222	(1)
Addition of ammonia derivatives	222	(1)
Oxidation of aldehydes	223	(1)
α-halogenation of ketones	223	(1)
Aldol condensation	224	(1)
Benzoin condensation	224	(1)
Carboxylic Acids	224	(3)
Ester formation	224	(1)
Nonreversible ester formation	225	(1)
Methyl ketone formation	225	(1)
Amide formation	225	(1)
Acid halide formation	226	(1)
Anhydride formation	226	(1)
Decarboxylation-Hunsdiecker reaction	226	(1)
Decarboxylation with copper salts	227	(1)
Reduction of carboxylic acids	227	(1)
Esters	227	(1)
Reduction	227	(1)
Acid halide	228	(1)
Acyl Halides	228	(1)
Esterification	228	(1)
Anhydride formation	228	(1)
Amide formation	229	(1)
Acid formation	229	(1)
Anhydrides	229	(1)
Ester formation	229	(1)
Amide formation	230	(1)
Acid formation	230	(1)
Amines	230	(3)
Ammonium ion formation	230	(1)
Amide formation	231	(1)
Benzene sulfonamide formation	231	(1)
Oxidation	231	(1)
Reaction with nitrous acid	231	(1)
Reaction of diazonium salt	232	(1)
Appendix A: Glossary	233	(25)
Appendix B: Periodic Table of the Chemical Elements	258	(2)
Appendix C: Electronegativity Values	260