Chem 210 PSU exam 4

What is the second reagent used in the following conversion?

(a) NaNH2
(b) KMnO4
(c) BH3
(d) Br2
(e) HBr

Correct answer: A

What is the order of stability of the carbocations shown below? [Note A > B means that
A is more stabilized than B.]
(a) A > B > C
(b) A > C > B
(c) B > A > C
(d) B > C > A
(e) C > A > B
(f) C > B > A

Correct answer: E

Which of the following compounds has the highest oxidation level?

Correct answer: ABCDE

Approximately, what is the yield of the chloride shown below obtained by

monochlorination of 2-methylbutane?
(a) 33%
(b) 27%
(c) 21%
(d) 14%
(e) 9%

Correct answer: D

What is the expected order of reactivity of the following bromides in SN2 reactions?
[Note A > B means that A reacts faster than B.]
(a) A > B > C
(b) A > C > B
(c) B > A > C
(d) B > C > A
(e) C > A > B
(f) C > B > A

Correct answer: E

What is the product of the following sequence of reactions?

Correct answer: D

For the following reaction, doubling the concentration of 1 has no effect on the reaction
rate. Doubling the concentration of 2 has no effect on rate, but it decreases the yield of
5 and increases the yield of 4. What are the mechanisms at work?
(a) SN1 and E1
(b) SN1 and E2
(c) SN2 and E1
(d) SN2 and E2
Correct answer: A

How many alkene products, including stereoisomers, might form in E1 elimination of the
alcohol shown below?
(a) 2
(b) 3
(c) 4
(d) 5
(e) 6

Correct answer: D

Which alkyl halide will yield only the product shown below in an E2 elimination process?
[Hint: Draw the Newman projections or build models].

Correct answer: A

The reaction of methoxide (CH3O- ) with 2-bromobutane gives the substitution product
shown below. Elimination products also form. Which structure represents the 2-
bromobutane used as the reactant in this reaction?

Correct answer: E

Consider the following backside displacement reaction of (S)-(-)-1-iodo-2-methylbutane

(1) to produce (+)-2-methyl-1-butanol (2). What is the absolute configuration of the
product?
(a) R
(b) S
(c) R and S (racemic mixture)
(d) R and S (unequal amounts)

Correct answer: B

How many constitutional isomers of the mono bromo product will form in the following
reaction?
(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Correct answer: C

What is the ΔHrxn (in kcal/mol) of the following reaction?

(a) -27
(b) -21
(c) -5
(d) 0
(e) 17
(f) 33

Correct answer: A

Based on the retrosynthetic analysis shown below, what is the reagent used in the first
synthetic step of the preparation of the target molecule? [Hint: pay attention to
stereochemistry.]
(a) CH2I2/Zn(Cu)
(b) Li/NH3(ℓ)
(c) mCPBA
(d) BH3; H2O2/NaOH
(e) NaNH2
(f) H2/Lindlar
Correct answer: B
What is the expected order of reactivity of the following bromides in SN1 reaction? [Note
A > B means that A reacts faster than B.]
(a) A > B > C
(b) A > C > B
(c) B > A > C
(d) B > C > A
(e) C > A > B
(f) C > B > A

Correct answer: F

The retrosynthetic analysis for synthesis of a deuterated (D = 2 H) substrate is sketched

below. What is the structure of the intermediate?

Correct answer: D

What is the outcome of the following reaction?

Correct answer: C
Which bromide will not yield a persistent Grignard reagent upon treatment with Mg?

Correct answer: E

What is the order of stability for radicals shown below, starting with the most stable?
(a) A > B > C
(b) A > C > B
(c) B > A > C
(d) B > C > A
(e) C > A > B
(f) C > B > A

Correct answer: B

Which product cannot be made from phenylacetylene 1, in a "one-step" reaction? Note:

A "one-step" reaction includes all regents needed to finish the reaction, even if added
stepwise (BH3; H2O2/NaOH, for example are consider one-step). Using a regent in
excess also counts as one step reaction.

Correct answer: C

Which of the following SN2 reactions would be the fasted if run with the same
concentrations of reactants and at the same temperature?
Correct answer: B

The following transformation is carried out in three steps (I-III). What are the appropriate
reagents for the third (III) step?
(a) (CH3)2CuLi +
(b) CH3I
(c) PBr3
(d) H2/Pd
(e) BH3; H2O2/NaOH

Correct answer: A

How many monochlorides formed in the following reaction are chiral?

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Correct answer: C

The radical chlorination of 1 gives 2 (among other products). What is true about the 1,2-
dichlorocyclopetanes (2) formed?
(a) two stereoisomers, one chiral
(b) three stereoisomers, two chiral
(c) three stereoisomers, one chiral
(d) two stereoisomers, both achiral
(e) three stereoisomers, all achiral

Correct answer: B
Which compounds can serve as an immediate precursor in the synthesis of butanal, 1?
Immediate precursor is a substance that can be converted into the target in one step.
(a) A only
(b) B only
(c) C only
(d) A and B
(e) A and C
(f) B and C
(g) all three

Correct answer: D