this document contain an helpful revision and practice questions and answers for organic 1

PRACTICE PROBLEMS Exam # 2 Spring 2014 2013


1) Among the following alkyl halides, choose the one with the lowest boiling
point.
A) t-butyl chloride
B) n-butyl chloride
C) t-butyl bromide
D) n-butyl iodide
E) t-butyl iodide
Answer: A


2) Which of the following compounds is the most nucleophilic?
A) CH3SH
B) CH3OH
C) H2O
D) CH3CO2H
E) BF3
Answer: A


3) Rank the following molecules in order of increasing relative rate of SN1
solvolysis with methanol and heat (slowest to fastest reacting).




A) 3 < 2 < 4 < 5 < 1
B) 2 < 3 < 4 < 1 < 5
C) 5 < 4 < 3 < 2 < 1
D) 2 < 3 < 4 < 5 < 1
E) 1 < 2 < 5 < 4 < 3
Answer: B

, 4) Which of the following alkyl halides is most likely to undergo rearrangement in
an SN1 reaction?
A) 3-bromopentane
B) 2-chloro-3,3-dimethylpentane
C) 3-chloropentane
D) bromocyclohexane
E) 1-bromo-4-methylcyclohexane
Answer: B


5) How many distinct alkene products are possible when the alkyl iodide below
undergoes E2 elimination?




A) 1
B) 2
C) 3
D) 4
E) 5
Answer: E

6) What two atomic orbitals or hybrid atomic orbitals overlap to form the C–H
bond in ethylene?
A) C sp3 + H s
B) C sp2 + H s
C) C sp + H s
D) C p + H s
Answer: B

7) Consider molecules with the formula C10H16. Which of the following
structural features are not possible within this set of molecules?
A) 2 triple bonds
B) 1 ring and 1 triple bond
C) 2 rings and 1 double bond
D) 2 double bonds and 1 ring
E) 3 double bonds
Answer: A