Solutions_Manual_for_Organic_Chemistry_6th_Ed 174

Solutions_Manual_for_Organic_Chemistry_6th_Ed 174 - 8-21...

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Unformatted text preview: 8-21 The chiral products shown here will be racemic mixtures. H (b) 1 (C)H3C plus enantiomer (e) CH3 ,OH Rr + 8-22 (a) (c) -;61 ; Br _ HO (y CH C H3 ,Cl plus enantiomers CI2 H (y Rr .. .. H� plus enantiomer C CI KOH !t,. C1 (d) H3C l-! HO / plus enantiomer ,----< ' \""",'CH-� H Cl � H2O H2SO4 !t,. ~ C l 8-23 (a) � (d) -0-< (b) � 8-24 Limonene, CIOH16, has three elements of unsaturation. Upon catalytic hydrogenation, the product, CIOH20, has one element of unsaturation. Two elements of unsaturation 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 or one triple bond. (The structure of limonene is shown in the text in Problem 8-23(d), and the hydrogenation product is shown above in the solution to 8-23(d).) 8-25 The BINAP ligand is an example of a conformationally hindered biphenyl as described in text section 5 -9A and Figure 5 -1 7 . The groups are too large to permit rotation around the single bond connecting the rings, so the molecules are locked into one chiral twist or its mirror image. "rear" H2O O 6 CI2 (y (c) C):) .. CH3 ,OH (b) 60 .. Cl CI2 H2O 6. . .. CI 0H "front" "front" naphthalene naphthalene ring nng These simplified three-dimensional drawings of the enantiomers show that the two naphthalene rings arc twisted almost perpendicular to each other, and the large -P(Phh substituents prevent interconversion of these mirror images. 167 ...
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