Organic Chemistry

Chapter 12 Alkenes, Alkynes, and Aromatic Compounds 12.5 Aromatic Compounds General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 1 Benzene Structure Benzene has 6 electrons shared equally among the 6 C atoms is also represented as a hexagon with a circle drawn inside

General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 2 Aromatic Compounds in Nature and Health General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 3 Naming Aromatic Compounds Aromatic compounds are named

with benzene as the parent chain with one side group named in front of benzene CH3 Methylbenzene General, Organic, and Biological Chemistry Cl Chlorobenzene Copyright 2010 Pearson Education, Inc. 4 Some Common Names

Some substituted benzene rings have common names that have been used for many years with a single substituent use a common name or are named as a benzene derivative. CH3 Toluene (methylbenzene) General, Organic, and Biological Chemistry OH NH2 Aniline (benzenamine)

Phenol (hydroxybenzene) Copyright 2010 Pearson Education, Inc. 5 Aromatic Compounds with Two Groups When two groups are attached to a benzene ring, number the ring to give the lowest numbers to the side groups (IUPAC) or use prefixes to show the arrangement of the substituents (common) on the ring ortho (o) for 1,2meta (m) for 1,3para (p) for 1,4-

General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 6 Examples of Aromatic Compounds with Two Groups OH Cl CH3 Cl

Cl Cl 3-Chlorotoluene (m-chlorotoluene) 1st and 3rd carbons 1,4-Dichlorobenzene (p-dichlorobenzene) Substituent's on 1st and 4th carbons General, Organic, and Biological Chemistry 2-Chlorophenol (o-chlorophenol) 1st and 2nd carbons

Copyright 2010 Pearson Education, Inc. 7 Xylene For isomers of dimethylbenzene, the common name xylene may be used General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 8 Learning Check Select the correct name(s) for each of the following compounds:

1) chlorocyclohexane Cl 2) chlorobenzene 3) 1-chlorobenzene CH3 CH3 General, Organic, and Biological Chemistry 1) 1,2-dimethylbenzene 2) 1,3-dimethylbenzene 3) m-xylene Copyright 2010 Pearson Education, Inc. 9 Solution

Select the correct name(s) for each of the following compounds: Cl 2) chlorobenzene CH3 CH3 General, Organic, and Biological Chemistry 2) 1,3-dimethylbenzene 3) m-xylene Copyright 2010 Pearson Education, Inc. 10

Learning Check Draw the condensed structural formulas for each of the following: A. 1,3-Dichlorobenzene B. o-Chlorotoluene General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 11 Solution Draw the condensed structural formulas for each of the following: A. 1,3-Dichlorobenzene Cl

Cl B. o-Chlorotoluene CH3 Cl General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 12 Learning Check Identify the organic family for each of the following: A. CH3CH2CHCH2

B. C. CH3CCH D. General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 13 Solution Identify the organic family for each of the following: A. CH3CH2CHCH2 alkene B.

cycloalkane (alkane) C. CH3CCH alkyne D. aromatic General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 14

Properties of Aromatic Compounds Aromatic compounds have a stable aromatic bonding system are resistant to many reactions undergo substitution reactions, which retain the stability of the aromatic bonding system General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 15 Substitution Reactions In a substitution reaction, a hydrogen atom on a benzene ring is replaced by an atom or group of

atoms. Type of substitution H on benzene replaced by Halogenation Chlorine or bromine atom Nitration Nitro group (NO2)

Sulfonation SO3H group General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 16 Halogenation In the halogenation of benzene an H atom of benzene is replaced by a chlorine or bromine atom a catalyst such as FeCl3 is needed in chlorination

a catalyst such as FeBr3 is needed in bromination General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 17 Nitration In the nitration of benzene, an H atom of benzene is replaced by a nitro (NO2) group from HNO3 an acid catalyst such as H2SO4 is needed General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc.

18 Sulfonation In the sulfonation of benzene, an H atom on benzene is replaced by a SO3H group from SO3 an acid catalyst such as H2SO4 is needed General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 19 Learning Check Write the equation for the bromination of benzene,

including the catalyst. General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc. 20 Solution Write the equation for the bromination of benzene, including the catalyst. H + Br2 General, Organic, and Biological Chemistry Br

FeBr3 + HBr Copyright 2010 Pearson Education, Inc. 21

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