508 CARBOXYLIC ACIDS (d) Undecane is the unbranched alkane with 1l carbon atoms, undecanoic acid is the correspond- carboxylic acid, and undecenoic acid is an 11-carbon carboxylic acid that contains a double bond. Because the carbon chain is numbered beginning with the carboxyl group, 10-undecenoic acid has its double bond at the opposite end of the chain from the carboxyl group H,C=CH(CH2)&CO,H 10-Undecenoic acid (undecylenic acid) (e) Mevalonic acid has a five-carbon chain with hydroxyl groups at C-3 and C-5, along with a methyl group at C-3 HOCH,CH, CCH,CO, H 3. 5-Dihydroxy-3-methylpentanoic acid (f) The constitution represented by the systematic name 2-methyl-2-butenoic acid gives rise to CH CH=CCO.H 2-Methy 1-2-butenoic acid Tiglic acid is the e isomer and the z isomer is known as angelic acid. The higher ranked sub stituents,methyl and carboxyl, are placed on opposite sides of the double bond in tiglic acid and on the same side in angelic acid. H,C H3 (E)-2-Methyl-2-butenoic (Z)-2-Methyl-2-butenoic acid (g) Butanedioic acid is a four-carbon chain in which both terminal carbons are carboxylic acid groups. Malic acid has a hydroxyl group at C-2. HOCCHCHCOH h) Each of the carbon atoms of propane bears a carboxyl group as a substituent in 1, 2, 3-propane- tricarboxylic acid. In citric acid C-2 also bears a hydroxyl group COH HO, CCH, CCH, CO,H 2-Hydroxy-1, 2, 3-propanetricarboxylic acid Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website(d) Undecane is the unbranched alkane with 11 carbon atoms, undecanoic acid is the correspond￾ing carboxylic acid, and undecenoic acid is an 11-carbon carboxylic acid that contains a double bond. Because the carbon chain is numbered beginning with the carboxyl group, 10-undecenoic acid has its double bond at the opposite end of the chain from the carboxyl group. (e) Mevalonic acid has a five-carbon chain with hydroxyl groups at C-3 and C-5, along with a methyl group at C-3. ( f) The constitution represented by the systematic name 2-methyl-2-butenoic acid gives rise to two stereoisomers. Tiglic acid is the E isomer, and the Z isomer is known as angelic acid. The higher ranked sub￾stituents, methyl and carboxyl, are placed on opposite sides of the double bond in tiglic acid and on the same side in angelic acid. (g) Butanedioic acid is a four-carbon chain in which both terminal carbons are carboxylic acid groups. Malic acid has a hydroxyl group at C-2. (h) Each of the carbon atoms of propane bears a carboxyl group as a substituent in 1,2,3-propane￾tricarboxylic acid. In citric acid C-2 also bears a hydroxyl group. HO2CCH2CCH2CO2H OH CO2H 2-Hydroxy-1,2,3-propanetricarboxylic acid (citric acid) HO2CCHCH2CO2H OH 2-Hydroxybutanedioic acid (malic acid) C C H H3C CO2H CH3 (E)-2-Methyl-2-butenoic acid (tiglic acid) C C H H3C CH3 CO2H (Z)-2-Methyl-2-butenoic acid (angelic acid) CH3CH CCO2H CH3 2-Methyl-2-butenoic acid HOCH2CH2CCH2CO2H OH CH3 3,5-Dihydroxy-3-methylpentanoic acid (mevalonic acid) 10-Undecenoic acid (undecylenic acid) H2C CH(CH2)8CO2H 508 CARBOXYLIC ACIDS __ __ __ Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website