Partial table of contents:
Carbon Compounds and Chemical Bonds.
Representative Carbon Compounds.
An Introduction to Organic Reactions: Acids and Bases.
Alkanes and Cycloalkanes: Conformations of Molecules.
Stereochemistry: Chiral Molecules.
Alkenes and Alkynes I: Properties and Synthesis.
Alkenes and Alkynes II: Addition Reactions.
Radical Reactions.
Alcohols and Ethers.
Conjugated Unsaturated Systems.
Aromatic Compounds.
Reactions of Aromatic Compounds.
Aldehydes and Ketones I: Nucleophilic Additions to the Carbonyl Group.
Aldehydes and Ketones II: Aldol Reactions.
Carboxylic Acids and Their Derivatives: Nucleophilic Substitution a the Acyl
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Carbon.
Amines.
Carbohydrates.
Lipids.
Answers to Selected Problems.
Glossary.
Index.
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C OMPOUNDS AND C HEMICAL B ONDS
1.1 INTRODUCTION
1. Organic chemistry is the study of the compounds of carbon. J J J J J J J J
2. The compounds of carbon are the central substances of which all living things on this
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planet are made.J J
1) DNA: the giant molecules that contain all the genetic information for a given
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species.
2) proteins: blood,muscle, and skin. J J J
3) enzymes: catalyzethe reactionsthat occurinourbodies. J J J J J J J
4) furnish the energy that sustains life.
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3. Billion years ago most of the carbon atoms on the earth existed as CH4:
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1) CH4,H2O,NH3,H2 were the main components of the primordial atmosphere.
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2) Electrical discharges and other forms of highly energetic radiation caused these
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simple compounds to fragment into highly reactive pieces which combine into more
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complex compounds such as amino acids, formaldehyde, hydrogen cyanide, purines,
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and pyrimidines.
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3) Amino acids reacted with each other to form the first protein.
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4) Formaldehyde reacted with each other to become sugars, and some of these sugars, J J J J J J J J J J J J J
together with inorganic phosphates, combined with purines and pyrimidines to
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become simple molecules of ribonucleic acids (RNAs) and DNA.
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4. We live in an Age of Organic Chemistry:
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1) clothing: J J natural or synthetic substance. J J J
2) householditems: J
3) automobiles:
4) medicines:
5) pesticides:
5. Pollutions:
1) insecticides: J J J natural or synthetic substance. J J J
2) PCBs:
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3) dioxins:
4) CFCs:
1.2 THE DEVELOPMENT OF ORGANIC CHEMISTRY AS A SCIENCE
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1. The ancient Egyptians used indigo (藍靛) and alizarin (茜素) to dye cloth.
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2. The Phoenicians (腓尼基人) used the famous “royal purple (深藍紫色)”, obtained
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from mollusks (墨魚、章魚、貝殼等軟體動物), as a dyestuff.
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3. As a science, organic chemistry is less than 200 years old.
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1.2A Vitalism
“Organic” ––– derived from living organism
J J J J J (In 1770, Torbern Bergman, Swedish
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chemist)
thestudy ofcompounds extracted fromliving organisms
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suchcompoundsneeded “vital force” tocreatethem
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1. In 1828, Friedrich Wöhler Discovered:
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O
NH4+ −OCN heat
H 2N C NH2
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Ammonium cyanate J Urea J
(inorganic) (organic)
1.2 B Empirical and Molecular Formulas J J J
1. In 1784 Antoine Lavoisier ( 法國化學家拉瓦錫) first showed that
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organic compounds were composed primarily of carbon, hydrogen, and oxygen.
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2. Between 1811 and 1831, quantitative methods for determining the composition of
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