Examination QUESTIONS AND
VERIFIED CORRECT
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If there is a NO2 group present, what IUPAC prefix will also be evident? - CORRECT ANSWER-
nitro
What is the predicted reaction? 1º alkyl halide with a strong base? weak base? poor
nucleophile? - CORRECT ANSWER-strong base: Sn2 favored but E2 with strong non-nucleophilic
bases
weak base: Sn2
poor nucleophile: no reaction
What is the predicted reaction? 2º alkyl halide with a strong base? weak base? poor
nucleophile? - CORRECT ANSWER-strong base: mostly E2
strong non-nucleophilic bases: mostly Sn2
poor nucleophile: Sn1/E2 (slow) in polar, protic solvents
What is the predicted reaction? 3º alkyl halide with a strong base? weak base? poor
nucleophile? - CORRECT ANSWER-strong base: E2
, strong non-nucleophilic bases: Sn1/E1 in polar protic solvents
poor nucleophile: Sn1/E1 in polar, protic solvents
What is the configuration of the product in the base-catalyzed hydrolysis of (R)-1-choloro-1-
deuteriobutane? - CORRECT ANSWER-(S)-1-deuterio-1-butanol (Sn2)
Where is the largest molecule on the periodic table? - CORRECT ANSWER-Bottom lefthand
corner
Nucleophilic strength increase with increasing what? - CORRECT ANSWER-atomic size
Which alkyl valid would you expect to undergo Sn1 hydrolysis most rapidly?
I, Br,Cl, or F? - CORRECT ANSWER-I
In which reaction is a racemic mixture obtained?
In which reaction is an inversion of chirality obtained? - CORRECT ANSWER-inversion: Sn2
racemic mix: Sn1
Cleavage of an ether usually requires a strong acid that has a conjugate base which is a strong
nucleophile, such as...? Depending on the type of alkyl group, the acid reaction with the halide
ion produces what? - CORRECT ANSWER-HBr
HI
alkyl halide and an alcohol
When chirality rotates clockwise the chirality is... - CORRECT ANSWER-R
When chirality rotates counterclockwise the chirality is... - CORRECT ANSWER-S