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

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Presentation on theme: "1 Organic Chemistry Chapter 24b-c Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display."— Presentation transcript:

1 1 Organic Chemistry Chapter 24b-c Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

2 2 Aromatic Hydrocarbons C C C CC C H H H H H H C C C CC C H H H H H H Electron micrograph of benzene resonance structure ? delocalized molecular orbitals

3 3 Other Representations of Benzene

4 4 Aromatic Compound Nomenclature CH 2 CH 3 ethylbenzene Cl chlorobenzene NH 2 aminobenzene NO 2 nitrobenzene Br 1,2-dibromobenzene Br 1,3-dibromobenzene o-dibromobenzenem-dibromobenzene

5 5 Aromatic Compound Nomenclature phenyl group benzene minus one hydrogen CH 3 – CH – CH 3 2-phenylpropane

6 6 Aromatic Compound Reactions H H H H H H Br H H H H H + HBr+ Br 2 FeBr 3 catalyst H H H H H H CH 2 CH 3 H H H H H + HCl+ CH 3 CH 2 Cl AlCl 3 catalyst Substitution reaction (atom or group of atoms replaces a H)

7 7 Polycyclic Aromatic Hydrocarbons benzene rings fused together

8 8 Functional Group Chemistry Alcohols contain the hydroxyl functional group and have the general formula ROH.

9 9 C 6 H 12 O 6 (aq) 2CH 3 CH 2 OH (aq) + 2CO 2 (g) enzyme CH 2 CH 2 (g) + H 2 O (g) CH 3 CH 2 OH (g) H 2 SO 4 Biological production of ethanol Commercial production of ethanol Metabolic oxidation of ethanol CH 3 CH 2 OH CH 3 CHO + H 2 alcohol dehydrogenase acetaldehyde

10 10 Functional Group Chemistry Ethers have the general formula ROR. CH 3 OH + HOCH 3 CH 3 OCH 3 + H 2 O H 2 SO 4 catalyst Condensation Reaction

11 11 Functional Group Chemistry Aldehydes and Ketones contain the carbonyl ( ) functional group. O C R C H O aldehydes have the general formulaR C R O ketones have the general formulaH C H O H C O CH 3 C O H3CH3C formaldehydeacetaldehydeacetone

12 12 Functional Group Chemistry Carboxylic acids contain the carboxyl ( COOH ) functional group.

13 13 Generally weak acids React with alcohols to form esters Neutralization Production of acid halides (intermediates in syntheses) Properties and Reactions of Carboxylic Acids

14 14 Functional Group Chemistry Esters have the general formula RCOOR, where R is a hydrocarbon group. Hydrolysis Alkaline hydrolysis (saponification) Characteristic odors and flavors

15 15 Functional Group Chemistry Amines are organic bases with the general formula R 3 N (RNH 2 ). CH 3 NH 2 + H 2 O RNH OH - CH 3 CH 2 NH 2 + HCl CH 3 CH 2 NH 3 + Cl - Neutralization

16 16 Some Aromatic Amines

17 17

18 Example 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) Br 2, (b) H 2 (in the presence of a Pt catalyst), (c) CH 3 COOH.

19 Example 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. (a)The reaction with bromine results in the addition of bromine to the double-bonded carbons, which become single- bonded.

20 Example 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.

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

22 22 Chemistry In Action: The Petroleum Industry Crude Oil

23 23


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