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Solutions_Manual_for_Organic_Chemistry_6th_Ed 174

Solutions_Manual_for_Organic_Chemistry_6th_Ed 174 - 8-21...

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8 -21 The chiral products shown here will be racemic mixtures. (e) plus enantiomer CH3 ,OH (y Rr + (b) 1 _ -; ; 61 CH3 ,Cl (y Rr Br plus enantiomers 8-22 C l (a) CI2 ~ .. H2O CH O H 6 (c) H2SO4 .. !t,. 8-23 H (C)H3C H C1 HO C ( b) CI2 .. H2O plus enantiomer CI 6 KOH !t,. CH3 ,OH (y Cl .. (d) 0 l-! ' H3C ,- -- -< Cl / \"", HO H " ' CH-� plus enantiomer CI CI2 6 ... . 0H .. H2O (a) (b ) (c) C):) ( d) -0-< 8-2 4 Limonene, CIOH16, has three elements of unsaturation. Upon catalytic hydrogenation, the product, CI O H20, 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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