(1)

How many electrons can occupy the d-subshell of an atom?

		A.	2
		B.	10
		C.	8
		D.	6
		E.	14

(2)

Water, H2O, has

		A.	4 bonding pair of electrons
		B.	3 bonding pair and 1 lone pair of electrons
		C.	2 bonding pair and 2 lone pair of electrons
		D.	2 sigma (s) bonds and two pi (p) bonds

(3)

Which of the following statements is true?

		A.	Covalent bonds are characterized by equal sharing of electrons between atoms.
		B.	Ionic bonds buildup electron density between atoms.
		C.	Ionic bonds are MUCH stronger than covalent bonds.
		D.	Covalent bonds are directionally oriented in space, whereas ionic bonds are not.
		E.	Ionic bonds occur between non-metals.

(4)

Which of the following has the most polar X-H bonds?

		A.	CH4
		B.	NH3
		C.	H2O
		D.	HF
		E.	HCl

(5)

How many constitutional isomers does C5H12 have?

		A.	1
		B.	2
		C.	3
		D.	4
		E.	5

(6)

How many of the constitutional isomers of C5H12 are branched?

		A.	1
		B.	2
		C.	3
		D.	4
		E.	5

(7) Using the IUPAC naming system, how many of the C5H12 constitutional isomers will have a name ending in "pentane"?              A. 1   B. 2   C. 3   D. 4   E. all of them       (8) The least stable conformation of 1,2-dichloroethane is              A. I   B. II   C. III   D. IV   E. V       (9) Which of the following C6H12 isomers would have the highest heat of combustion?              A. propylcyclopropane   B. ethylcyclobutane   C. methylcyclopentane   D. cyclohexane   E. Since they all have the same formula, they are all the same.       (Use the following information for questions 10-11.) Again, considering the polar reaction we used in class for an example of reaction mechanisms and the following reaction profile: (10) Which point(s) represent transition state(s)?              A. 2 only   B. 3 only   C. 4 only   D. 2 and 4   E. 2, 3, and 4       (11) Which point(s) represent an intermediate?              A. 2 only   B. 3 only   C. 4 only   D. 2 and 4   E. 2, 3, and 4

(12)

Twist ethylene (II below) is less stable than regular ethylene (I below) because

		A.	the staggered arrangement of the H atoms decreases stability.
		B.	the eclipsed arrangement of the H atoms increases the local dipole moment.
		C.	the activation energy for transition to the twist form is higher than to the regular form.
		D.	dipole moments no longer cancel one another out.
		E.	orbital overlap, and hence bonding, is reduced.

(13)

The reaction in the previous question is an example of

		A.	hydroboration
		B.	oxidation
		C.	anti addition
		D.	syn addition
		E.	none of these is correct

(14)

Addition of HBr to propene produces bromopropane in good yield in the presence of peroxides. Which of the following statements is correct? I. The addition is anti-Markovnikov.II. The addition is Markovnikov.III. The reaction is a radical chain reaction.IV. The reaction is a radical polar reaction.

		A.	I only
		B.	II only
		C.	I and III
		D.	I and IV
		E.	II and III

(15)

What characteristic of alkynes would make it difficult to prepare cyclohexyne?

		A.	requirement for linearity at the triple bond
		B.	large electron density between carbons in a triple bond
		C.	short C-C distance in triple bonds
		D.	the C-C triple bond must be internal to the chain
		E.	all of these

(16)

Which of the following are unusual about the acetylide anion and serves to make it a useful reactant?

		A.	A H cleaved a C is unique in reactivity.
		B.	A carbocation (C electrophile) is produced.
		C.	A carbanion (C nucleophile) is produced.
		D.	None of these is particularly significant.
		E.	Given differing reaction conditions, all of these are true.

(17)

Which of the following molecules has the S stereochemical orientation?

		A.
		B.
		C.
		D.
		E.	none of these

(18)

Which of the following is a relatively insignificant factor affecting the magnitude of specific optical rotation?

		A.	concentration of the optically active substance
		B.	purity of the sample
		C.	temperature of the measurement
		D.	length of the sample tube
		E.	all are significant

(19)

What is the product of the reaction of cyclohexene with N-bromosuccinimide (NBS)?

		A.	bromocyclohexane
		B.	2-bromocyclohexene
		C.	1,2-dibromocyclohexane
		D.	hexane
		E.	cyclohexane

(20)

What role does NBS serve in the reaction in reaction above?

		A.	Produces a highly reactive bromide anion.
		B.	Produces a Br• radical.
		C.	Produces Br2 for addition to the double bond.
		D.	Provides and oxidant to cleave the double bond.
		E.	Produces H2 for addition to the double bond.

(21)

Which of the following characteristics do SN1 reactions possess? I. unimolecular kinetics II. two step process III. do NOT completely invert stereochemical configuration

		A.	I and II only
		B.	II and III only
		C.	II only
		D.	none of these
		E.	all of these

(22)

Which of the following is the BEST leaving group for SN2 reactions?

		A.	I—
		B.	F—
		C.	OAc—
		D.	MeO—
		E.	H2N—

(23)

If the following substrate is chiral, which of following reaction mechanisms would result in a racemic mixture of products?

		A.	SN1
		B.	SN2
		C.	E1
		D.	E2
		E.	More than one of the above.

(24)

Electromagnetic radiation interacts with molecules at a variety of levels. Which of the following correctly lists the type of interaction with a molecule (in order) for infrared, UV-Visible, and NMR experiments?

		A.	vibrational, nuclear spin, electronic transitions
		B.	vibrational, electronic transitions, nuclear spin
		C.	electronic transitions, vibrational, nuclear spin
		D.	electronic transitions, nuclear spin, vibrational
		E.	nuclear spin, electronic transitions, vibrational

(25)

How many 1H NMR signals (unsplit by spin coupling) would cis-1,2-dichlorocyclopropane give?

		A.	one
		B.	two
		C.	three
		D.	four
		E.	five

(26)

How many (unsplit) 13C NMR signals would cis-1,2-dichlorocyclopropane give?

		A.	one
		B.	two
		C.	three
		D.	four
		E.	five

(27)

Which of the following statements is (are) true?

		A.	Aromatic protons are downfield of alkene protons.
		B.	Aromatic protons are upfield of alkene protons.
		C.	TMS is downfield of all other molecules.
		D.	Electron withdrawing groups result in more shielded protons.
		E.	More than one of the above is true.

(28)

The 1,4 monoaddition product(s) for HCl reacting with 2,4-hexadiene is(are)

		A.	No reaction.
		B.	5-chloro-2-hexene
		C.	4-chloro-2-hexene
		D.	2-chloro-3-hexene
		E.	more than one of the above

(29)

What is the product when benzene reacts with H2 over Ni?

		A.	1,3-cyclohexadiene
		B.	cyclohexene
		C.	cyclohexane
		D.	n-hexane
		E.	No reaction occurs as the ring is inert.

(30)

Which of the following conjugated cyclic polyenes is aromatic? I. C7H7 II. C8H8 III. C10H10

		A.	I and II only
		B.	II and III only
		C.	III only
		D.	I
		E.	all of the above

(31)

A student in lab class runs a nitration reaction using two substrates. The first is chlorobenzene and the second is toluene. Which of the following statements is TRUE?

		A.	The reactions proceed at the same rate.
		B.	The reaction with chlorobenzene proceeds more rapidly.
		C.	The reaction with toluene proceeds more rapidly.
		D.	It is not possible to differentiate between the two in terms of rate.

(32)

Which of the following statements is(are) true about electrophilic addition to benzene? I.One of the sets of  electrons acts as a nucleophile. II.One of the sets of  electrons acts as an electrophile. III. Powerful electrophiles are required for reaction to occur.

		A.	I and II
		B.	II and III
		C.	I and III
		D.	all of these

(33)

Which of the following statements is(are) true about electrophilic aromatic substitution (EAS) to toluene? I.Certain resonance forms make the ring more reactive than benzene. II.Certain resonance forms make the ring less reactive than benzene. III. Inductive effects make the ring more reactive than benzene.

		A.	I
		B.	II
		C.	III
		D.	none of these

(34)

Which of the following pairs of reagents can be used to prepare 2-methyl-3-pentanol?

		A.
		B.
		C.
		D.

(35)

Ethers share which of the following characteristics? I. Generally chemically inert. II. Vulnerable to acid-catalyzed cleavage. III. Vulnerable to base-catalyzed cleavage. IV. Generally insoluble in water, even when small.

		A.	I and II
		B.	II and III
		C.	I and IV
		D.	II, III, and IV
		E.	I, II, and IV

(36)

Epoxides (oxiranes) are highly reactive species. Which of the following statements best accounts for this observation?

		A.	The carbocation is stabilized.
		B.	The resulting carbanion is stabilized.
		C.	A stable, inert ether is formed on reaction.
		D.	The C—O bond is strengthened by adjacent groups.
		E.	The three-membered ring is highly strained.

(37)

Nucleophilic addition reactions to carbonyl groups can be catalyzed by either bases or acids. Acid catalyzes these reactions by

		A.	making the C of the carbonyl group more electrophilic.
		B.	making the C of the carbonyl group more nucleophilic.
		C.	shifting the equilibrium of the reaction.
		D.	being a powerful nucleophile itself.
		E.	none of these.

(38)

Reaction of a primary amine with an aldehyde or ketone produces

		A.	an amide
		B.	a secondary amine
		C.	a nitrile
		D.	an imine
		E.	none of these.

(39)

Which of the following is characteristic of the IR spectrum of carboxylic acids?

		A.	A broad strong peak between 3300 and 3500 cm-1.
		B.	A broad strong peak between 2500 and 3300 cm-1.
		C.	A strong narrow peak around 1750 cm-1.
		D.	a and b
		E.	b and c

(40)

The following molecule is classified as a(n)

		A.	amide.
		B.	carboxylic acid.
		C.	acid anhydride.
		D.	lactone.
		E.	acid halide.

(41)

Which of the following carboxylic acid derivatives is the most reactive towards nucleophilic acyl substitution.

		A.	amides
		B.	acid chlorides
		C.	acid anhydrides
		D.	nitriles
		E.	esters

(42)

The molecule below exists in equilibrium between the two forms shown. Which of the following statements best describes the equilibrium position for this system?

		A.	Equilibrium to the left is preferred to vast excess.
		B.	Equilibrium to the right is preferred to vast excess.
		C.	Equilibrium to the left is unusually high for this general type of system due to resonance stabilization.
		D.	Equilibrium to the right is unusually high for this general type of system due to resonance destabilization.
		E.	Transformation between the forms above can be accomplished only by acid catalysis. The transformation reaction does NOT occur in basic solution.

(43)

Which of the following is true about enolate anions? I. Prepared by the addition of base to a carbonyl with an a-H. II. Prepared by the addition of acid to a carbonyl with an a-H. III. More reactive than an enol form of the original carbonyl. IV. More likely to react as an electrophile than a nucleophile.

		A.	I, III, and IV
		B.	II, III, and IV
		C.	I and III
		D.	I and IV
		E.	II and III

(44)

What is the product when an aldol is dehydrated?

		A.	an acid anhydride
		B.	malonate diester
		C.	b-hydroxyaldehyde
		D.	conjugated enone
		E.	b-ketoester

(45)

Which of the following best describes what happens in an aldol condensation reaction?

		A.	The acid catalyst activates on aldehyde so that it can act as an electrophile and attack an unactivated molecule.
		B.	The base abstracts an a hydrogen producing an electrophile that reacts with an unactivated aldehyde.
		C.	The base abstracts an a hydrogen producing an nucleophile that reacts with an unactivated aldehyde.
		D.	Two moles of aldehyde are consumed in an endothermic reaction, caused water to condense into a vapor and form droplets on the inside of the reaction vessel.
		E.	The reaction initially forms and enol moiety, which rearranges to the keto form.

(46)

Arenediazonium salts are prepared by reaction of

		A.	nitrobenzene with H2SO4 and HNO2
		B.	nitrobenzene with sodium ethoxide in alcohol
		C.	aniline with sodium ethoxide in alcohol
		D.	aniline with H2SO4 and HNO2
		E.	None of these.

(Use the following reaction sequence for questions 47-49. Assume that product from the previous reaction is present for the next step.)

(47)

Which of the following is Product 1?

		A.	aniline
		B.	arenediazonium salt
		C.	p-chloroaniline
		D.	m-chloroaniline
		E.	p-nitrochlorobenzene

(48)

Which of the following is Product 2?

		A.	p-chloroaniline
		B.	chlorobenzene
		C.	2,4-dichloroaniline
		D.	3,4-dichloraniline
		E.	3,4-dichloronitrobenzene

(49)

Which of the following is Product 3?

		A.	aniline
		B.	benzene
		C.	1,3-dichlorobenzene
		D.	1,2-dichlorobenzene
		E.	3,4-dichloroaniline

(50)

Reaction of an arenediazonium salt with which of the following sets of reagents would produce nitrobenzene?

		A.	nitric acid
		B.	nitrous acid
		C.	hyponitrous acid
		D.	N2 gas bubbled through the solution.
		E.	None of these.