Solutions_Manual_for_Organic_Chemistry_6th_Ed 94

Solutions_Manual_for_Organic_Chemistry_6th_Ed 94 - 5 1 6(a...

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Unformatted text preview: 5- 1 6 (a) H + C OOH CH3 OH HO e nantiomer + s ame C OOH CH3 H CH3 enantiomer + OH H COOH HO + s ame C H3 C H3 COOH H R ules for Fischer projections: Br + C H3 C H3 C H2CH3 H Br + CH3 CH3 C H2CH3 1I H + + CH3 enantiomer e nantiomer C H2CH3 OH C H2CH3 Br ( c) HO + CH3 H C H3 CH2CH3 H H + CH2CH3 OH HO + CH2CH3 H H 1 . Interchanging any two groups an odd number of times (once, three times, etc . ) makes a n enantiomer. Interchanging any two groups an even number of times (e.g. twice) returns to the original stereoi somer. 2. Rotating the structure by 90 0 makes the enantiomer. Rotating by 1 800 returns to the original stereoisomer. (The second rule is an application of the first. Prove this to yourself.) ( R)-2-butanol 5- 1 7 HO C H20H e n anti omer same s ame (a) + 5- 1 8 (a) C H20H 1 80 0 rotation of the right structure does not give left structure ; n o plane of symmetry: c hiral�nantiomers - - - - -Br + (:H 3 , C H20H H f' o n the left ; also has plane of symmetry: s ame structure 1 80 0 rotation of the ri ght structure gi ves same structure as (c ) �� Br + , Br p lane of symmetcy same structure 87 ...
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