8-21 The chiral products shown here will be racemic mixtures. (e) plus enantiomer CH3 ,OH (yRr + (b) 1 _ -;;61 CH3 ,Cl (yRr Br plus enantiomers 8-22 Cl (a) � CI2 ~ .. H2O CHOH 6 (c) H2SO4 .. !t,. 8-23 H (C)H3CHC1 HO C� (b) CI2 .. H2O plus enantiomer CI 6 KOH !t,. CH3 ,OH (yCl .. (d) 0 l-! ' H3C,----<Cl / \"", HO H"'CH-� plus enantiomer CI CI2 6 .... 0H .. H2O (a) � (b)� (c) C):) (d) -0-< 8-24 Limonene, CIOH16, has three elements of unsaturation. Upon catalytic hydrogenation, the product, CIOH20, has one element of unsaturation. Two elements of un saturation have been removed by hydrogenation-these must have been pi bonds, either two double bonds or one triple bond. The one remaining unsaturation must be a ring. Thus, limonene must have one ring and either two double bonds
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