(1)

What is the major product ( X ) when styrene (shown below) is reacted with H2 over a Ni catalytic surface?

		A.
		B.
		C.
		D.
		E.	No reaction occurs under these conditions.

(2)

Which product(s) would be produced by acid catalyzed dehydration of the following alcohol?

		A.	2-methylpentene
		B.	2-methyl-2-pentene
		C.	2-methylpentene and 2-methyl-2-pentene
		D.	4-methyl-1-pentene

(3)

What product would result from the reaction of 1,2-dimethylcyclohexene with hydrogen gas in the presence of a Pt catalyst?

		A.
		B.
		C.
		D.	a and c
		E.	all of the molecules shown above will be produced in this reaction

(4)

The role of peroxides in the polymerization of ethylene is

		A.	radical producing chain initiator
		B.	Lewis Acid producing chain initiator
		C.	polar reaction catalyst
		D.	radical producing chain propagator
		E.	radical producing chain terminator

(5)

A triple bond is composed of:

		A.	three sigma bonds
		B.	two sigma bonds and one pi bond
		C.	one sigma bond and two pi bonds
		D.	sp3 bonds
		E.	sp bonds

(6)

Which of the following is required to form an acetylide anion?

		A.	a VERY powerful base.
		B.	a terminal alkyne
		C.	peroxides
		D.	a and b
		E.	b and c

(7) Which of the following is a good operational way to identify a chiral center?              A. Determine if a plane of symmetry exists.   B. Determine if there are four different attachments at a carbon center.   C. Check for the existence of mirror images.   D. See if the molecule is optically active (i.e. does it have color).       (8) The reaction shown below can be said to be:              A. stereoselective.   B. regioselective.   C. both a and b   D. neither a nor b   E. The answer choices make no sense in this context.       (9) Molecules that rotate plane polarized light to the left are              A. levorotary   B. dextrorotary   C. R   D. S   E. Z       (The following information and answer choices will be used for Questions 10 — 11.) Classify the following pairs of compounds as A. enantiomers B. diasteroemers C. identical D. identical and meso compounds E. different chemical comounds and not isomeric (10)              A.   B.   C.   D.   E.       (11)              A.   B.   C.   D.   E.

(12)

Why is preparing a monohaloalkane by radical reaction with X2 a poor reaction synthetically?

		A.	The reaction is slow.
		B.	The reaction is not regioselective.
		C.	The reaction requires enormous light flux to begin.
		D.	The reaction is massively exothermic and produces a huge amount of heat.
		E.	The reaction is not stereoselective.

(13)

Which of the following is the most stable radical?

		A.
		B.
		C.
		D.

(14)

Why is SOCl2 used instead of HCl to replace —OH groups on secondary alcohols?

		A.	SOCl2 is resonance stabilized, leader to faster reaction.
		B.	There are no radical byproducts with SOCl2.
		C.	SOCl2 has a steric advantage over the chloride anion.
		D.	Reactions are run under mild conditions, leading to fewer rearrangements.

(15)

Which of the following reagents are used to produce a Grignard Reagent?

		A.	Ge / H3O+
		B.	RX / Mg
		C.	RH / NBS
		D.	SOCl2 / Mg
		E.	THF / Mg

(Use the following for questions 16 — 17.) The monosubstitution reaction of methane with Cl₂ proceeds by a stepwise radical mechanism in the presence of UV light. Classify each of the following reactions as:

A. chain doubling
B. chain initiating
C. chain propagating
D. chain terminating
E. none of these

(16)

		A.
		B.
		C.
		D.
		E.

(17)

		A.
		B.
		C.
		D.
		E.

(18)

Consider nucleophilic substitution reactions of alkylhalides, where a moderately reactive nucleophile is used. Under which of the following sets of conditions is the SN2 mechanism most likely predominant?

		A.	primary substrate, acidic conditions
		B.	secondary substrate, acidic conditions
		C.	tertiary substrate, acidic conditions
		D.	secondary substrate, basic conditions
		E.	cannot differentiate

Use the following reaction for Questions 19 and 20.

(19)

What is the predominant mechanism type for both reactions?

		A.	SN1
		B.	SN2
		C.	E1
		D.	E2
		E.	radical

(20)

Which reaction is faster and why?

		A.	A, because F- is a better leaving group that I-
		B.	B, because I- is a better leaving group that F-
		C.	A, because F stabilizes the reactant better than I
		D.	B, because I stabilizes the reactant better than F
		E.	The reaction rates are equivalent.

Use the following answer choices for questions 21 - 24.

I.	substitution	VI.	unimolecular
II.	elimination	VII.	nucleophilic
III.	addition	VIII.	electrophilic
IV.	rearrangement	IX.	single step
V.	bimolecular	X.	multiple step

(21)

An E1 reaction is:

		A.	VIII, IX
		B.	VIII, IV, IX
		C.	VIII, VI
		D.	II, IX
		E.	II, VI

(22)

An SN1 reaction is:

		A.	I, VIII
		B.	I, VI, IX
		C.	I, X
		D.	III, VI
		E.	III, VII, X

(23)

An E2 reaction is:

		A.	II, IX, V
		B.	II, X, VI
		C.	II, IX, VI
		D.	IV, VIII, VI
		E.	IV, VIII, IX

(24)

An SN2 reaction is:

		A.	I, X
		B.	I, IX, VII
		C.	I, V, X
		D.	III, V
		E.	III, X

(25)

A synthetic chemist performed a series of reactions designed to produce bonds between C and N. On analysis of the IR spectra of the resulting compounds, there were characteristic bands resulting from various types of C•••N connections. The observed bands fell into three ranges: 1. 1020-1250 cm-1 2. 1471-1689 cm-1 3. 2000-2273 cm-1 The bands were assigned (in order 1, 2, 3) to functional groups as:

		A.	amine, nitrile, imine
		B.	amine, imine, nitrile
		C.	nitrile, amine, imine
		D.	nitrile, imine, amine
		E.	imine, nitrile, amine