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Chapter 12

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CHY 152
Robert Gossage

CHY152-Introduction to Organic Chemistry Chapter 12: Unsaturated Hydrocarbon Summary (All page references are according to Ed. 6 textbook of Chemistry for Today)  Unsaturated hydrocarbons belong to three classes alkenes, alkynes, and aromatic hydrocarbons  Acetylene (simplest alkyne), ethylene (simplest alkene), benzene (simplest aromatic)  Aromatic hydrocarbons contain 3 double bonds and alternating 3 single bonds  Alkenes and alkynes are called unsaturated because more H atoms can be added similarly like more solute can be added to an unsaturated solution  C (sp2) and H (1s) in alkenes  Cis-trans stereoisomers is found only in alkenes that have 2 different group atoms to each double-bonded carbon  Markonvinkov’s rule of H-X adds to an alkene, the H becomes attached to the C atom that is already bonded to more hydrogens …remember the phrase “the rich gets richer”  Suffix of alkene -ene  General formula of alkene: CnH2n  Chemists learned the term “aromatic” was not accurate, though its still used today but with a different meaning which is they contain the characteristics of benzene ring or its structure relative  Compounds that do not contain that kind of a structure are called nonaromatic compounds and are referred to as aliphatic compounds  Alkenes, alkanes, alkynes are, therefore, aliphatic compounds  Molecular structure of benzene, introduced by Michael Faraday  Benzene’s condensed structural formula indicates its highly unsaturated, however, it is not!  C (sp2) in benzene  In 1965, a German chemist named Freidrich August Kekule von Stradonitz suggest and represented by a ring arrangement of C atoms with alternation single and double bonds  When a single H of benzene ring is replaced, the following can be named as a derivative of benzene: ethyl benzene, nitrobenzene, etc  When # of benzene derivatives are known by common names that are IUPAC accepted: toluene, aniline, benzoic acid, phenol, etc  Compounds
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