Chem 210 PSU exam 3

How many degrees of unsaturation does C10H11BrN2O3 have?

(a) 2
(b) 3
(c) 4
(d) 5
(e) 6
Correct answer: E

Enthalpies of formation (ΔHf) and hydrogenation (ΔHH) for 1 and 2 are given below.
What is ΔH (in kcal/mol) of the following reaction?
(a) -2.0
(b) -1.5
(c) 0
(d) 1.0
(e) 1.5

Correct answer: E

What is the product of the following reaction? [D is an isotope of hydrogen that reacts
identically.]

Correct answer: A

What is the major product of the reaction shown below run at low temperature?

Correct answer: D
Which starting alkene may be used to synthesize 1 in a one-step reaction?

Correct answer: C

Which structure has an E double bond?

Correct answer: B

What is the most precise description of stereochemistry of the product of the following
equation?

Correct answer: D

What is the product of the reaction shown below? [D is an isotope of hydrogen that
reacts identically.]

Correct answer: B

What is the correct order of stability for the alkenes shown below, starting with the least
stable? [Note: A < B indicates that A is less stable 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 reagents will not result in syn stereochemistry of the product
when reacted with an alkene?
(a) H2/Pd
(b) OsO4/NMO
(c) Cl2
(d) mCPBA
(e) BH3
Correct answer: C

What is the product of the reaction shown below?

Correct answer: E

Which of the following bromides is not likely to form upon HBr addition to 4-methylhex2-
ene (1)? [Hint: Do not neglect rearrangements.]

Correct answer: D

An alkene A was oxidized with OsO4/NMO to give only the following product. Which
statement is correct?
(a) A was optically active
(b) A was a Z isomer
(c) A was a E isomer
(d) A was a mixture of E and Z isomers

Correct answer: B

Treatment of cyclohexene (1) with ICl yields the dihalide product 2. Which species is the
most likely reactive intermediate in this transformation?

Correct answer: A
What is the product of the following reaction? [D is an isotope of hydrogen that reacts
identically.]
Correct answer: C

What is the structure for the most likely rearrangement product?

Correct answer: E

The electrophilic addition reaction shown below yields only 2. Which statement about
this reaction is correct?
(a) The addition is anti and N3 (azide) acts as the electrophile.
(b) The addition is syn and N3 (azide) acts as the electrophile.
(c) The addition is anti and I (iodine) acts as the electrophile.
(d) The addition is syn and I (iodine) acts as the electrophile.

Correct answer: C

What is produced by treatment of alkene 1 with ozone followed by a reductive workup?

(a) a racemic mixture
(b) a single enantiomer of the product
(c) a mixture of diastereomeric products
(d) a meso product

Correct answer: B

What is the correct ranking the carbocations below in terms of increasing stability?
(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: C

Treatment of propene (1) with DCl (D = deuterium, an isotope of hydrogen that reacts
identically) leads to a deuterio-chloropropane species 2. Which alkene(s), 3 or 4, when
allowed to react with HCl, would produce the same propane derivative 2?
(a) 3 only
(b) 4 only
(c) both
(d) neither

Correct answer: B

The following reaction is catalyzed by an enzyme bromoperoxidase that delivers Br+ to

the substrate. Which double bond forms the initial bromonium ion and which acts as a
nucleophile to react with the bromonium ion?
double bond double bond acting
forming bromonium ion as a nucleophile
(a) A B
(b) A C
(c) B A
(d) B C
(e) C A
(f) C B

Correct answer: A

How many alkene products, including stereoisomers, might form by dehydration of the
alcohol shown below?
(a) 2
(b) 3
(c) 4
(d) 5
(e) 6
Correct answer: D

What is the correct order of reactivity with HBr for the alkenes shown below, starting
with the least reactive stable? [Note: A < B indicates 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: A

What is the product of the following reaction?

Correct answer: A

Addition of HBr to (R)-4-bromo-1-pentene (1) yields only 2,4-dibromopentane. What is

true about the stereochemistry of the product?
(a) a racemic mixture is produced
(b) a mixture of unequal amounts of enantiomers is produced
(c) two chiral diastereomers are formed in equal amounts
(d) a mixture of unequal amounts of diastereomers is produced of which only one is
chiral
Correct answer: D