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CHEM1280 Midterm Exam, 1st term 2012-2013

(2:30 to 3:30 pm, 7 Nov. 2012)

Name : __________ __________ ____ Student ID: __________ __________ __

Section 1 (85 points totally)

1. Choose the one correct answer for each of the following questions (50 points)

(1) (2) (3) (4) (5) (6) (7) (8) (9) (10)
D B C C C D A B A C

(1) Which of the following statements about propene is correct?

(A) All nine atoms lie in the same plane.
(B) The compound has a cis and trans isomer.
(C) It generally acts as an electrophile in the electrophilic addition reactions.
(D) There is a total of eight σ bonds in propene.
(E) All the carbon atoms are sp2 hybridized.

(2) When benzanilide reacts Br2, which of the following is the major product?

(3) Which of the following is not (S)-2-chlorobutane? (C is a Fischer projection)

(4) Which of the following shows the correct order of decreasing boiling point for the
concerned hydrocarbons?
(A) heptane > 2,2-dimethylpropane > 2-methylbutane > pentane
(B) 2-methylbutane > heptane > 2,2-dimethylpropane > pentane
(C) heptane > pentane > 2-methylbutane > 2,2-dimethylpropane
(D) 2-methylbutane > 2,2-dimethylpropane > pentane > heptane
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(5) When 1-methylcyclohexene reacts with CH3OH at the presence of H2SO4 as catalyst,
which of the following compounds is the major product?

(6) Upon hydrogenation to the same saturated hydrocarbon, which of the following
alkenes releases the most heat per mole?
(A) 1-hexene (B) cis-3-hexene (C) trans-1,3-hexadiene
(D) 1,5-hexadiene (E) trans-1,4-hexadiene

(7) Which of the following correctly ranks compounds I-IV in order of decreasing
reactivity toward electrophilic aromatic substitution?

(A) IV > I > III > II (B) IV > I > II > III
(C) II > III > I > IV (D) IV > III > II > I

(8) Which of the following correctly ranks compounds I-IV in order of decreasing
acidity?

(A) III > IV > I > II (B) IV > III > I > II
(C) II > IV > III > I (D) IV > III > II > I
(E) II > I > III > IV

(9) Which of the following structures represents a meso compound?

(10) Which of the following structures is the most stable?

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2. Name the following molecules with the systematic nomenclature using the R/S system for
the asymmetric centers and the E/Z system for alkenes when necessary. (6 points)

(S)-3-methylcyclohexene (E)-3-propyl-2-octene

3. 1) Draw skeletal structures for all the constitutional isomers of C5H10;

2) One of the above constitutional isomers exists as a pair of stereoisomers. Draw
skeletal structures for the two stereo isomers. What type of stereoisomers are they?
3) One of the above constitutional isomers exists as three stereo isomers. Draw
skeletal structures for the three stereoisomers. What type of stereoisomers are they?
(15 points)
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4. Compounds a-d are the major products for the following reactions. Draw skeletal
structures for a-d, showing stereochemisty of the product if the reaction is
stereoselective. (14 points)

Section 2. Choose only One questions from this section to answer. Please indicate which
question you want to be graded by circling the question number. If you answer all the two
questions in this section, the second one will not be graded. (15 points)

5. When reacting with acid, 4-pyrone is protonated on one of its oxygen atoms to give a
stable cation.
1) Draw the skeletal structure for this cation showing which oxygen atom is protonated;
2) Explain why this cation is so stable.
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6. As shown below, phenol can be conveniently iodized by ICl to yield 4-iodophenol.

1) Propose a reasonable mechanism for this reaction using curved arrows to show the
flow of electrons.
2) Explain why this reaction does not yield 3-iodophenol using the resonance structure
of the possible intermediate.
3) Explain why this reaction does not yield 4-chlorophenol.