Organic Chemistry Chapter 24b-c

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Organic Chemistry Chapter 24b-c Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

Aromatic Hydrocarbons resonance structure ? delocalized molecular orbitals Electron micrograph of benzene

Other Representations of Benzene

Aromatic Compound Nomenclature CH2CH3 ethylbenzene NH2 aminobenzene Cl chlorobenzene NO2 nitrobenzene Br Br 1 2 3 4 5 6 1,2-dibromobenzene 1,3-dibromobenzene o-dibromobenzene m-dibromobenzene

Aromatic Compound Nomenclature phenyl group benzene minus one hydrogen 2-phenylpropane CH3 – CH – CH3

Aromatic Compound Reactions Substitution reaction (atom or group of atoms replaces a H) H Br + HBr + Br2 FeBr3 catalyst H CH2CH3 + HCl + CH3CH2Cl AlCl3 catalyst

Polycyclic Aromatic Hydrocarbons benzene rings fused together

Functional Group Chemistry Alcohols contain the hydroxyl functional group and have the general formula R−OH.

Biological production of ethanol C6H12O6 (aq) 2CH3CH2OH (aq) + 2CO2 (g) enzyme Commercial production of ethanol CH2 CH2 (g) + H2O (g) CH3CH2OH (g) H2SO4 Metabolic oxidation of ethanol CH3CH2OH CH3CHO + H2 alcohol dehydrogenase acetaldehyde

Functional Group Chemistry Ethers have the general formula R−O−R′. Condensation Reaction CH3OH + HOCH3 CH3OCH3 + H2O H2SO4 catalyst

Functional Group Chemistry Aldehydes and Ketones contain the carbonyl ( ) functional group. O C R C H O aldehydes have the general formula R C R′ O ketones have the general formula H C H O H C O CH3 C O CH3 H3C formaldehyde acetaldehyde acetone

Functional Group Chemistry Carboxylic acids contain the carboxyl ( −COOH ) functional group.

Properties and Reactions of Carboxylic Acids Generally weak acids React with alcohols to form esters Neutralization Production of acid halides (intermediates in syntheses)

Functional Group Chemistry Esters have the general formula R′COOR, where R is a hydrocarbon group. Characteristic odors and flavors Hydrolysis Alkaline hydrolysis (saponification)

Functional Group Chemistry Amines are organic bases with the general formula R3N (RNH2). CH3NH2 + H2O RNH3+ + OH- Neutralization CH3CH2NH2 + HCl CH3CH2NH3+Cl-

Some Aromatic Amines

24.5 Cholesterol is a major component of gallstones, and it is believed that the cholesterol level in the blood is a contributing factor in certain types of heart disease. From the following structure of the compound, predict its reaction with (a) Br2, (b) H2 (in the presence of a Pt catalyst), (c) CH3COOH.

24.5 Strategy To predict the type of reactions a molecule may undergo, we must first identify the functional groups present (see Table 24.4). Solution There are two functional groups in cholesterol: the hydroxyl group and the carbon-carbon double bond. The reaction with bromine results in the addition of bromine to the double-bonded carbons, which become single-bonded.

24.5 Strategy To predict the type of reactions a molecule may undergo, we must first identify the functional groups present (see Table 24.4). Solution There are two functional groups in cholesterol: the hydroxyl group and the carbon-carbon double bond. (b) This is a hydrogenation reaction. Again, the carbon-carbon double bond is converted to a carbon-carbon single bond.

24.5 (c) The acid reacts with the hydroxyl group to form an ester and water. Figure 24.10 shows the products of these reactions.

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