1)
Provide the reagents necessary to prepare 1-bromo-3-isobutylbenzene benzene.

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2)
How would you use 1H NMR spectroscopy to distinguish between the following two compounds?

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3)
Which one of the following compounds is most acidic? Explain your choice.

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4)
Explain why long-term storage of ethers can be dangerous.

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5)
Provide the reagents necessary to carry out the following conversion.

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6)
Provide the reagents necessary to carry out the following conversion.

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7)
How can you distinguish between cyclohexanol and cyclohexanecarboxylic acid using IR spectroscopy?

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8)
Provide the reagent(s) necessary to carry out the following conversion.

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9)
Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of Use structural drawings to explain your reasoning.

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10) Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.

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11) What is the correct IUPAC name for the molecule shown below?

A) 2-Methyl-5-propyl-3-heptyne
B) 5-Ethyl-2-methyl-3-octyne
C) 1-Isopropyl-3-ethyl-1-hexyne
D) 6-Methyl-3-propyl-4-heptyne
E) 4-Ethyl-7-methyl-5-octyne

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12)
What is the IUPAC name for the following compound?

A)
3-methyl-4-ethyl-3-hexen-6-ol
B)
4-ethyl-3-methyl-3,6-hexenol
C)
3-ethyl-4-methyl-3-hexen-1-ol
D)
3-methyl-4-(2-hydroxyethyl)-3-hexene
E)
3-(2-hydroxyethyl)- 3-methyl-3-hexene

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13)
Which of the indicated protons in the following compound would appear most upfield in the 1H NMR spectrum?

A)
I
B)
II
C)
III
D)
IV
E)
I & III

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14) Provide the reagent(s) required to complete the following transformation:

a. HBr
b. Br2/H2O
c. Br2
d. HBr/ROOR
e. hn /NBS

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15)
Which of the following electromagnetic radiation is used in NMR spectroscopy?
A)
UV
B)
IR
C)
visible
D)
g-rays
E)
radio wave

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16)
Which major product(s) are formed for the following reaction?


A)
I
B)
II
C)
III
D)
IV
E)
V

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17)
What is the IUPAC name for the following compound?

A)
2-methyl-5-bromocyclohexanol
B)
3-bromo-2-methylcyclohexanol
C)
1-bromo-4-methylcyclohexanol
D)
4-bromo-6-methylcyclohexanol
E)
4-bromo-2-methylcyclohexanol

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18) Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

A) 1) Br2; 2) H2, Lindlars cat
B) 1) H2, Lindlars cat.; 2) Br2
C) 1) Br2; 2) Na, NH3(l)
D) 1) Na, NH3(l); 2) Br2
E) 1) Br2, 2) H2, Pt

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19) Compound A has molecular formula C6H12. Upon treatment with NBS and irradiation with UV light, only two compounds (including stereoisomers) are formed. Suggest possible structures for compound A.

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20)
The Diels Alder reaction is a concerted reaction, which means
A)
The product contains a cyclic ring
B)
The diene must be in the s-cis conformation to react
C)
All changes in bonding (bond making and bond breaking) occur simultaneously
D)
It is an endothermic reaction
E)
Both exo and endo products are formed

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21)
Predict the product(s) for the following reaction.


A)
I
B)
II
C)
III
D)
IV
E)
none of these

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22) Select the reagent(s) expected to accomplish the transformation shown below.

A) H2, Ni
B) H2, Ni2B
C) Na, NH3(l)
D) A and B
E) B and C

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23) What is the IUPAC name for the expected product of the transformation below?

A) Propyne
B) 1-Hexyne
C) 2-Hexyne
D) 3-Hexyne
E) (E)-3-Hexyne

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24)
Which one of the following compounds will have the highest wavenumber for C=C absorption?

A)
I
B)
II
C)
III
D)
IV
E)
V

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25) For the reaction below, how many different organic products would be expected?

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

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26) Provide the systematic IUPAC name for Cl3C(CH2)4CCH.
A) 4,4,4-Trichloro-1-butyne
B) 1,1,1-Trichloro-6-heptyne
C) 1,1,1-Trichloro-5-heptyne
D) 6,6,6-Trichloro-1-hexyne
E) 7,7,7-Trichloro-1-heptyne

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27)
Predict the major product for the following reaction.


A)
I
B)
II
C)
III
D)
IV
E)
none of these

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28)
Electrospray ionization is used to obtain mass spectra of proteins because:
A)
it allows for faster fragmentation of molecular ion
B)
the molecular ion usually does not undergo fragmentation
C)
it allows for slow fragmentation of molecular ion
D)
none of these

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29)
What is the correct IUPAC name for the following compound?

A)
12-crown-5
B)
12-crown-4
C)
4-crown-12
D)
12-crown-12
E)
none of these

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30) The expected major product from the treatment of 1-pentyne with 2 equivalents of HBr is:
A) 1-bromo-1-pentene
B) 2-bromo-1-pentene
C) 1,1-dibromopentane
D) 2,2-dibromopentane
E) 1,2-dibromopentane

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31) Which statement below best explains acetylenes Ka being greater than ethylenes?
A) Acetylide anions are resonance stabilized
B) The 4 p electrons of the acetylide anion better stabilize a negative charge
C) The electronegativity of sp carbons being greater than sp2 carbons
D) The electronegativity of sp carbons being less than sp2 carbons
E) Acetylene has only two hydrogen atoms while ethylene has four

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32)
Predict the product, for the following reaction sequence,
A)
6,7-dimethyl-3-nonanol
B)
6,7-dimethyl-3-nonanone
C)
6,7-dimethyl-3-nonanal
D)
3,4-dimethyl-7-nonanol
E)
3,4-dimethyl-7-nonanone

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33) What mechanistic intermediate is used to explain the preference for addition of the Br atom, of HBr, to the internal carbon of a terminal alkyne?
A) Formation of a more stable primary vinylic carbocation
B) Formation of a more stable secondary vinylic carbocation
C) Addition of the H atom to the carbon already with an H
D) Addition of H, from HBr, to the least hindered carbon
E) Steric hindrance for the approach of the Br atom to the primary carbon

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34)
Which of the following isomer(s) of tribromoaniline will show two doublets with 7.5 Hz coupling in 1HNMR spectrum?

A)
I
B)
II
C)
III
D)
IV
E)
II & IV

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35)
What is the common name for the following compound?

A)
1-butoxybutane
B)
sec-butyl isopropyl ether
C)
sec-butyl t-butyl ether
D)
n-butyl isopropyl ether
E)
none of these

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36) Provide the reagent(s) expected to accomplish the transformation shown below:

A) H2, Pt
B) Na, NH3(l)
C) H2, Ni2B
D) NaOEt
E) H2SO4, H2O

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37)
Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

A)
disrotatory, cis-3,4-diethylcyclobutene
B)
conrotatory, cis-3,4-diethylcyclobutene
C)
disrotatory, trans-3,4-diethylcyclobutene
D)
conrotatory, trans -3,4-diethylcyclobutene

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38)
For the following conversion, identify if the starting material has been oxidized, reduced or neither.

A)
reduced
B)
oxidized
C)
neither
D)
A & B

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39)
What is the main difference between an aromatic and antiaromatic compound?
A)
Aromatic compounds must be cyclic and planar, but not antiaromatic compounds
B)
Aromatic compounds must be monocyclic
C)
Antiaromatic compounds must have a conjugated system with p orbital at every vertex
D)
Aromatic compounds must satisfy Hckels rule
E)
none of these

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40)
Which one of the following reactions would produce t-butyl methyl ether in high yield?
A)
CH3ONa + (CH3)3CBr
B)
CH3OH + (CH3)3COH in presence of H2SO4 at 140C
C)
CH3Cl + (CH3)3CBr in presence of NaOH
D)
(CH3)3CONa + CH3Br

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41) Which term best describes the process shown below?

A) initiation
B) propagation
C) termination
D) elimination
E) inhibition

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42) Which of the compounds listed would be a final major product for the following reaction sequence?

A) I
B) II
C) III
D) IV
E) V

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43) What functional group would be expected to be found in the major, and final, organic product upon completion of the reaction between 1-hexyne and a mixture of mercuric sulfate and aqueous sulfuric acid?
A) aldehyde
B) ketone
C) diol
D) ether
E) carboxylic acid

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44)
Provide the reagents necessary to carry out the following conversion.

A)
KMnO4, NaOH, H2O
B)
KMnO4, H3O+, 75oC
C)
H2SO4, heat
D)

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45)
Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

A)
disrotatory, cis-5,6-diethyl-1,3-cyclohexadiene
B)
conrotatory, cis-5,6-diethyl-1,3-cyclohexadiene
C)
disrotatory, trans-5,6-diethyl-1,3-cyclohexadiene
D)
conrotatory, trans -5,6-diethyl-1,3-cyclohexadiene

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46)
Which of the following is the base peak in the mass spectrum of 2,2,4-trimethylpentane?
A)
114
B)
57
C)
42
D)
29
E)
none of these

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47) What is the correct IUPAC name for the molecule shown below?

A) 6-Bromo-3-octyne
B) 6-Bromo-6-methyl-3-heptyne
C) 2-Bromo-2-methyl-4-heptyne
D) 6-Bromo-6,6-dimethyl-3-hexyne
E) 2-Bromo-4-octyne

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48)
Predict the product for the following reaction.

A)
I
B)
II
C)
III
D)
IV

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49)
Which of these is the rate-determining step in the electrophilic aromatic substitution of benzene?
A)
Formation of an electrophile
B)
Formation of sigma complex
C)
Loss of proton from sigma complex
D)
Addition of electrophile & loss of proton
E)
None of these

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50)
The number of electrons present in an aromatic compound:
A)
4n + 2
B)
2n + 2
C)
4n
D)
none
E)
None of these

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51)
Provide the structure for (E)-1,3-pentadiene.

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52) Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2-butanol.

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53)
Predict the product(s) for the following reaction.

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54) Using correct arrow formalism, draw all the resonance structures for the radical shown below.

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55)
Provide the reagents necessary to carry out the following conversion.

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56)
Determine the multiplicity and predict the chemical shifts of each signal in the expected 1H NMR spectrum of the following compound.

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57) Both compounds A and B have molecular formula C6H14. Monochlorination of compound A results in formation of two constitutional isomers. Monochlorination of compound B results in formation of four constitutional isomers. Identify compounds A and B, and show the products of each monochlorination.

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