Question

1. Draw the structure of the principal organic product and predict the stereochemistry to be expected from the reaction of (IR, 2R)-/-bromo-2-methylcyclohexane with each of the following: a. NaOCH, in CH,OH at 60° d. NaNH, in NH, dt 50° b. aqueous CH OH at 140° e. aqueous CH.CH,OH at 25° c. Nal in DMSO at 40° 2. Draw the major product(s) (showing appropriate stereochemistry when necessary) for the following reactions. Indicate the mechanism(s) in operation (SNI,SN2, El. or E2). CH, OH NaSH acetone CH2CH2CH3 a BH CH.CH NaOCH2CH3 b. Mi HOCH2CH3 NaNH2 NH3 Nal NaOCHE HOCH DMSO CH3 3. When 1-chloro-2-butene reacts in 50% aqueous acetone at 50', the product is a mixture of two alcohols. CH,CH=CHCHCl ------> CH-CH=CHCH2OH + CH-CH(OH)CH=CH, (56%) (44%) Write out a detailed MECHANISM that accounts for these experimental facts. (HINT: The intermediate is "resonance stabilized".)

Answer 1

SN2 reaction gives inversion of configuration via transition state.

SN1 mechanism gives retention of configuration via carbocation intermediate.

BY CHONA T Home Acho M nant WO tat 2147 LLLLLLLLLLLLLLLLLLLLLLLLLLLLLL

12. a Brt TTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTT СНЫ СЕ СН, CH₂CH₂CH₂ HLOCHA HOCHO CH₂CH3 CH2CH₂ Noot Nao El the - E2 c. Na ochz CH₃ ott Nash a – SNL SNL CH3 HapH DMSO Grotte LLLL L LLLLLLLLLLLLLLLL LLLLLLLLLLLLLLL