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Which dimethylcyclobutane is chiral?

A) 1,1-dimethylcyclobutane
B) trans-1,2-dimethylcyclobutane
C) cis-1,2-dimethylcyclobutane
D) cis-1,3-dimethylcyclobutane

What is the relationship between an enantiomer's configuration and its specific rotation?

A) There is no relation
B) R are dextrorotatory
C) R are levorotatory

(+)-Mandelic acid has a specific rotation of +158 degrees. What specific rotation would be observed for a sample with 50% optical purity?

A) 39.5 degrees
B) 00.0 degrees
C) 52.7 degrees
D) 79.0 degrees

Which best defines a meso compound?

A) a molecule with a plane of symmetry and no chiral center
B) a molecule that cannot be superposed on its mirror image even though it has no chiral centers
C) a molecule that has no mirror image
D) a molecule that can be superposed on its mirror image and that does contain chiral centers

Which of the following compounds is a meso compound?

A) trans-1,2-dichlorocyclopropane
B) 1,1-dichlorocyclopropane
C) cis-1-chloro-2-bromocyclopropane
D) cis-1,2-dichlorocyclopropane

If a molecule has 5 stereogenic center, it will have __?__ stereoisomers

A) 0
B) 5
C) 32
D) 25

This process occurs when both bonding electrons remain with one product fragment.

A) Heterolytic bond breaking
B) homolytic bond formation
C) radical formation
D) homolytic bond breaking

How many degree of unsaturation are in valium (diazepam),?

A) 12
B) 10
C) 11
D) 7

In a radical reaction, the following step, is an example of___?___.
Cl⋅+CH3-CH2-CH3 → CH3-CH-CH3 + HCl

A) termination
B) addition
C) initiation
D) propagation

The reason that the chemical shift for an alkyne hydrogen atom is upfield from an alkene hydrogen atom is:

A) it is more acidic than the alkene hydrogen atoms.
B) the alkyne carbon has a grate relative electronegativity due to the fact that it is sp hybridized.
C) there are 2 pi bonds for resonance in the alkyne versus only 1 pi bond in the alkene.
D) the anisotropic effect of the triple bond shields the alkyne hydrogen atoms whereas the anisotropic effect of the double bond deshields the alkene hydrogen atom.

Which of the following will be the most abundant fragment ion formed from 2-butanone in the mass spectrum? 

A) CH3-CH3+
B) CH3-CH2-C☰O:+
C) CH3
D) CH3-C☰O:+

Why is the infrared absorption for the stretching motion of internal alkynes rarely observed?

A) C☰C stretching does not change the dipole moment.
B) The force constant for stretching of C☰C is too high.
C) They are too strong.
D) They do not form cations.

Why is the oxygen-hydrogen absorption of CH3OH such a broad band in the infrared?

A) Rotational energy levels broaden the absorption.
B) Hydrogen bonding broadens the absorption.
C) Resonance broadens the absorption.
D) Hyperconjugation resonance broadens the absorption.

The beta alkene carbon atom (marked with a star) of the following compund will have a chemical shift in the carbon NMR spectrum _?_ than the normal shift for ethene () primarily due to _?_.
H2C★=CH-F

A) Less/inductive and/or anisotropic effects.
B) Greater/inductive and/or Anisotropic effects.
C) Less/resonance effects.
D) Greater/resonance effects.

What is the multiplicity expected in the ^1 spectrum for the hydrogen atoms marked by a "star" in the following compound?
CH3-C(=O)- ★CH2-CH3

A) Singlet
B) Triplet
C) Doublet
D) Quartet

What is the intensity ratio of the peaks of a quartet in a  spectra?

A) 1:2:2:1
B) 1:3:3:1
C) 1:1:1:1
D) 1:4:4:1

Which of the following molecule orbital diagrams for butadiene represents the highest occupied molecular orbital in the excited state?

A) ⇞-⇞↗⇞-⇞
B) ⇞-⇞↗⇟-⇟
C) ⇞-⇟↗⇟-⇞
D) ⇞-⇟↗⇞-⇟

The amount of energy in infrared light corresponds to:

A)  The amount of energy needed to promote one electron from a bonding to an antibonding molecular orbital.
B)  The amount of energy needed to strip a molecules of one electron to generate a cation radical.
C) The amount of energy needed to "flip" the spin of a 13C or a 1H nucleus.
D)  The amount of energy needed to increase certain molecules motions, such as bond vibrations.

The major monobromination product in the following reaction is:


A)  
B)
C)  
D)  

Which compounds give four signals in their ^1H spectra?
I. (CH3)2CHCH2CH3
II. H3CHC=CH2
III.CH3(Br)CHCH2CH3

A) I and III
B) II and III
C) II only
D) I only
E) III only
F) I and II
G) None of these
H) All of these

How many absorptions will the following compound have in its CMR spectrum?
CH3CH2CH=C(CH3)2

A) 4
B) none of these
C) 5
D) 2
E) 3

Which characterizes the splitting of the indicated protons in the structure below?
(Cl)CH=CHCH2Cl H's in trans

A) singlet
B) doublet of doublet
C) none of these
D) doublet
E) triplet

How many peaks are present in the NMR signal for the starred protons.
CH3-CH2-CH2-CH2-CH3

A) 3
B) 4
C) 2
D) 5
E) none of these

Which of the following alkene is expected to have the highest heat of hydrogenation?

A) cis-2-pentene
B) trans-2-pentene
C) 2-methyl-2-butene
D) 1-pentene

Which of the following is not a possible reaction of a carbocation?

A) Addition of a nucleophile
B) Addition of a proton to form an alkane
C) Loss of a Beta-hydrogen to form an alkene
D) Rearrangement to a more stable carbocation

Which statement most accurately describes why alkenes react the way they do?

A) A pi bond is lost but a stronger sigma bond is gained.
B) C=C double bonds are unstable.
C) C=C double bonds are weak.
D) C=C pi bonds are attacked by nucleophiles.

Addition of HCl to 3-methyl-1-pentene gives two products. one of these is 2-chloro-3-methylpentane. What is the other product?

A) 2-chloro-2-methylpentane
B) 3-chloro-3-methylpentane
C) 1-chloro-3-methylpentane
D) 3-chloro-2-methylpentane

Predict which of the following alkenes react the fastest with HCl.

A) CH3CH2CH2CH2CH=CH2
B) trans-CH3CH2CH=CHCH2CH3
C) (CH3)2C=CHCHH2CH3
D) cis-CH3CH2CH=CHCH2CH3

Which of the following alkenes gives 1-bromo-2-methyl-2-pentanol upon reaction with Br2/H2O?

A) CH3CH=CHCH(CH3)2
B) CH3CH2CH=C(CH3)2
C) CH3CH2CH2C-(CH3)=CH2
D) CH3CH2C-(CH3)HCH=CH2

Which of the following is least likely to react with an alkene?

A) H3O+
B) CH3CH2 (ethyl radical)
C) BrCl
D) NaOCH2CH3

The rearrangement which occurs in the following reaction can be described as a

(CH3)2CHCH=CH2 -HBr->
            3   2    1
A)  Hydride shift from C-3 to C-2.
B) Hydride shift from C-2 to C-1.
C)  Methyl shift from C-3 to C-2.
D)  Proton shift from C-2 to C-1.