BRCC CHM 102 Class Notes Chapter 13 Page 1 of 6
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1 BRCC CHM 102 ass Notes Chapter 13 Page 1 of 6 Chapter 13 Benzene and Its Derivatives aliphatic hydrocarbons include alkanes, alkenes, and alkynes aromatic hydrocarbons compounds that contain one or more benzene ring they are also called arenes An aromatic hydrocarbon group is called an aryl group (Ar ) Benzene - the simplest aromatic hydrocarbon with the molecular formula, C 6 H 6. discovered by Faraday should be unsaturated, but does not behave like it is (ex. does not react with 2 like alkenes do) undergoes substitution reactions rather than addition reactions C 6 H C 6 H 6 Fe 3 catalyst + H (a Chlorine is substituted for a Hydrogen) Kekule proposed the structure for benzene a 6 membered ring with alternating double bonds HC H C CH HC C H CH The concept of resonance was developed by Linus Pauling certain molecules or ions are best described by writing more than one Lewis structure. The real molecule is a mixture or hybrid of these resonance structures. Each of these resonance hybrids is called a contributing structure. < > In the above figure, there is an aromatic sextet a closed loop of 6 electrons which is characteristic of benzene rings. Compounds with resonance are very stable. The benzene ring is stabilized by resonance. These structures do not flip-flop the double bonds are delocalized or spread out over all 6 carbons.
2 BRCC CHM 102 ass Notes Chapter 13 Page 2 of 6 The 6 carbons share electrons to create a double donut shaped electron cloud. When benzene is drawn, it is understood that true benzene has a structure part way between the possible Lewis structures. The individual Lewis structures do not exist on their own. All of the following are equivalent: Aromatic compounds contain delocalized rings of electrons which contribute to resonance. Naming Benzene Derivatives: monosubstituted benzenes: CH 2 chlorobenzene nitrobenzene ethylbenzene bromobenzene common names: NH 2 CO toluene phenol aniline benzoic acid CHO O H C CH 2 C benzaldehyde anisole acetophenone styrene O
3 BRCC CHM 102 ass Notes Chapter 13 Page 3 of 6 disubstituted benzenes: When there are 2 groups, then 3 isomers are possible. ortho (1,2) meta (1,3) para (1,4) o-dichlorobenzene m-dichlorobenzene p-dichlorobenzene The 3 dimethyl benzenes have the common name, xylene. o-xylene m-xylene p-xylene When one of 2 groups produces a compound that has a common name, use the common name as the parent. o bromotoluene p nitrophenol When neither group produces a common name compound, then put them in alphabetical order.
4 BRCC CHM 102 ass Notes Chapter 13 Page 4 of 6 When there are 3 or more groups, use numbers like cycloalkanes. H 2 N 1,2,4 tribromobenzene 2,3 dinitroaniline 1,4 dibromo 2,6 dichlorobenzene (One of the s is given the number 1 because it comes first alphabetically.) When a benzene ring is used as a substituent, it is called a phenyl group, abbreviated Ph Do not confuse a phenyl group with a benzyl group. CH 2 phenyl group benzyl group Polynuclear Aromatic Hydrocarbons (PAHs) contain 2 or more aromatic rings. The 3 most common are: naphthalene anthracene phenanthrene
5 BRCC CHM 102 ass Notes Chapter 13 Page 5 of 6 Reactions of Aromatic Compounds aromatic substitutions Halogenation: + 2 Fe catalyst + H Nitration: + HNO 3 H SO H 2 O Sulfonation: + H 2 SO 4 SO 3 H benzenesulfonic acid + H 2 O Sulfonation is used to make synthetic detergents. They make up 90% of the market once held by soap. phenols - compounds containing - connected to an aromatic ring phenols are solids which are soluble in water and will dissolve most easily in a basic solution phenol itself is toxic The most important property of phenols is that they are weak acids. phenol can also refer to a class of compounds with the structure. phenols are widely found in nature (ex. capsaicin the chemical which makes peppers hot) carbolic acid - an aqueous solution of phenol used as an antiseptic.
6 BRCC CHM 102 ass Notes Chapter 13 Page 6 of 6 tricky naming stuff: H 3 C HO 3-methylphenol m-cresol 1,3-Benzenediol Remember: Alcohols are neutral, but phenols are acidic. Phenols will react with strong bases to form salts. Most do not react with weak bases. acid base reaction: O-Na+ + Na + H 2 O sodium phenoxide Triclosan, a phenol compound, is an antiseptic and disinfectant commonly used in deodorant products. O
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