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Chapter 12 Organic Compounds with Oxygen and Sulfur 1 12.3 Reactions of Alcohols and Thiols Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Dehydration of Alcohols 2 Alcohols undergo • dehydration when heated with an acid catalyst • the loss of –H and –OH from adjacent carbon atoms, producing an alkene H OH | | H—C—C—H | | H H alcohol H+, heat H—C=C—H + H2O | | H H alkene Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of 1 Alcohols 3 Alcohols undergo oxidation, increasing the number of carbon and oxygen bonds. Primary alcohols are oxidized to produce an aldehyde. 1 bond to O H OH | | H—C—C—H | | H H 1 alcohol 2 bonds to O oxidation H O | || H—C—C—H | H aldehyde Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of 1 Alcohols 4 Alcohols undergo oxidation, increasing the number of carbon and oxygen bonds. Aldehydes can further oxidize to produce a carboxylic acid. 1 bond to O H O | || H—C—C—H | H aldehyde 2 bonds to O oxidation H O | || H—C—C—OH | H carboxylic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of 2 Alcohols 5 Secondary alcohols are oxidized to produce a ketone. To indicate the process of oxidation, [O] is placed over the reaction arrow. 1 bond to O 2 bonds to O H OH H | | | H—C—C—C—H | | | H H H H O H | || | H—C—C—C—H | | H H [O] 2 alcohol Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition ketone Copyright © 2012 by Pearson Education, Inc. Oxidation of Tertiary 3 Alcohols 6 Tertiary (3) alcohols do not readily oxidize. OH CH3CCH3 CH3 3 alcohol [O] no product no H to oxidize no reaction Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation and Reduction 7 In an oxidation, • there is an increase in the number of C–O bonds • there is a loss of H In a reduction, • there is a decrease in the number of C–O bonds • there is a gain of H Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation and Reduction 8 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Methanol Poisoning 9 Methanol • is also known as methyl alcohol • is highly toxic and found in windshield washer fluid, Sterno, and paint strippers • is rapidly absorbed and oxidized to formaldehyde and then formic acid O [O] CH3OH O [O] HCH methyl alcohol formaldehyde HCOH formic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Ethanol, CH3CH2OH 10 Ethanol • acts as a depressant and kills or disables more people than any other drug • is metabolized at a rate of 12–15 mg/dL per hour by a social drinker • is metabolized at a rate of 30 mg/dL per hour by an alcoholic Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Effect of Alcohol on the Body 11 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Oxidation of Thiols 12 When thiols undergo oxidation, • an H atom is lost from each of two –SH groups • the product is a disulfide • protein in hair is cross-linked by disulfide bonds found in the amino acid cysteine Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 13 Select the product for the oxidation of OH CH3CHCH2CH3 [O] O A. CH3CH=CHCH3 B. CH3CCH2CH3 OH C. CO2 + H2O D. CH3CHCH2CH3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 14 Select the product for the oxidation of OH [O] CH3CHCH2CH3 O The answer is B. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition CH3CCH2CH3 Copyright © 2012 by Pearson Education, Inc. Learning Check 15 Select the product when CH3–CH2–CH2–OH undergoes each of the following reactions: [O] [O] CH3—CH2 —CH2OH B. C. 1) CH3—CH=CH2 2) CO2 + H2O O || 3) CH3—CH2—C—H O || 4) CH3—CH2—C—OH Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 16 Select the product when CH3–CH2–CH2–OH undergoes each of the following reactions: O [O] B. 3) || CH3—CH2—CH2OH CH3—CH2—C—H [O] O C. 4) || CH3—CH2—C—OH Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 17 Give the primary product for the reaction of 2-propanol when it undergoes A. oxidation B. dehydration Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 18 OH CH3CHCH3 = 2-propanol = C3H8O A. oxidation OH O 2CH3CHCH3 + 9O2 [O] CH3CCH3 + 6CO2 + 8H2O B. dehydration OH CH3CHCH3 H+, heat CH3CH=CH2 + H2O Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.