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15.5.5: Chapter 5

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    482459
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    Problem 5-1 Chiral: screw, shoe
    Problem 5-2
    (a) The structure of coniine, in which N is in first position. C2 is labeled with asterisk and bonded to a propyl group.
    (b) The wedge-dash structure of menthol. C1, C2, and C5 are labeled with asterisks.
    (c) The wedge-dash structure of dextromethorphan. Two fused carbons of both cyclohexanes and one carbon of central cyclohexane (that is bonded to nitrogen) are labeled with asterisks.
    Problem 5-4
    (a) The wedge-dash structure of threose. C2 and C3 are labeled with asterisks.
    (b) The wedge-dash structure of enflurane. C1 is labeled with asterisk.
    Problem 5-5 Levorotatory
    Problem 5-7
    (a) −Br
    (b) −Br
    (c) −CH2CH3
    (d) −OH
    (e) −CH2OH
    (f) −CH = O
    Problem 5-8
    (a) −OH, −CH2CH2OH, −CH2CH3, −H
    (b) −OH, −CO2CH3, −CO2H, −CH2OH
    (c) −NH2, −CN, −CH2NHCH3, −CH2NH2
    (d) −SSCH3, −SH, −CH2SCH3, −CH3
    Problem 5-9
    (a) S
    (b) R
    (c) S
    Problem 5-10
    (a) S
    (b) S
    (c) R
    Problem 5-13 Compound (a) is D-erythrose 4-phosphate, (d) is its enantiomer, and (b) and (c) are diastereomers.
    Problem 5-14 Five chirality centers and 25 = 32 stereoisomers
    Problem 5-16 Compounds (a) and (d) are meso.
    Problem 5-17 Compounds (a) and (c) have meso forms.
    Problem 5-20 Two diastereomeric salts: (R)-lactic acid plus (S)-1-phenylethylamine and (S)-lactic acid plus (S)-1-phenylethylamine
    Problem 5-21
    (a) Constitutional isomers
    (b) Diastereomers
    Problem 5-22
    (a) The wedge-dash structure of (S)-glyceraldehyde. The dash bonded hydrogen at C3 is labeled pro-R and wedge bonded hydrogen is labeled pro-S.
    (b) The wedge-dash structure of an amino acid. The wedge bonded hydrogen at C3 is labeled pro-R and the dash bonded hydrogen is labeled pro-S.
    Problem 5-23
    (a) The structure of hydroxyacetone. The central carbon is labeled Re face at the top and Si face at the bottom.
    (b) The structure of crotyl alcohol. The central carbon is labeled Re face at the top and Si face at the bottom.
    Problem 5-24 (S)-Lactate
    Problem 5-25 The −OH adds to the Re face of C2, and −H adds to the Re face of C3. The overall addition has anti stereochemistry.

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