Organic Test

66 Questions  I  By Mgaines
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1.  Arrange the followwing conformers of butane in order of energy, lowest to highest: eclipsed, totally eclipsed, gauche, and anti.
2.  When 3-iodo-3ethylpentane is heated in methanol, the major organic product is an_____ that is generated through an ____mechanism.
3.  Which of the following alkyl chlorides will undergo SN2 reaction most readily?
4.  What term describes the structural relationship between (E)- and (Z)-2-pentene?
A.
B.
C.
D.
E.
5.  Given the chloronation of acetone sown below, choose the correct rate law.   CH3COCH3 + Cl2 ® CH3COCH2Cl + HCl
A.
B.
C.
D.
E.
6.  Which of the following statements is(are) true for the compound (R)-butanol?
A.
B.
C.
D.
E.
7.  What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane?
8.  How do alkyl substituents stabilize a carbocationic center to which they are attached?
9.  Which of the folowing best descibes the molecules of a sample of ethane gas at room temperature?
10.  Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.
11.  The major product which results when 2-chloro2-methylpentane is heated in ethanol is an ether.
12.  Provide two  circumstances under which solvolysis of chiral alkyl halide would not result in the generation of a mixture of enantiomeric products. 
13.  Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?   I.                    Rate = k[base] II.                 Rate = k[base][RX] III.               Rate = k[RX] IV.              The reactions occur in two or more distinct steps. V.                    Rearrangements are sometimes seen.
14.  Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?
15.  Which of the statements below correctly descibes an achiral molecule?
16.  If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must is also contain?
17.  What is the major constituent of natural gas?
18.  Which of the following compounds will undergo an SN2 reaction most rapidly?
19.  Which of the following statements correctly pertains to a pair of enantiomers?
A.
B.
C.
D.
E.
20.  The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?
A.
B.
C.
D.
E.
21.  WWhich of the followwing is a primary alkyl halide?
22.  Which of the following is a vicinal dihalide?
A.
B.
C.
D.
E.
23.  If a mixture contains 75% of one compound and 25% of its enatiomer, what is the e.e of the mixture?
24.  Which of the following alkyl bromides undergoes solvolysis in aqueous methanol most rapidly?
25.  Which of the following is true for the termination step of free radical chlorination reaction?
26.  Which of the following correctly expressed the standard Gibbs free energy change of a reaction in terms of the changes in enthalpy and entropy?
A.
B.
C.
D.
27.  WWhich of the following solvents could be descibed as polar and protic?
28.  SN1 reactions usually proceed with:
29.  Which alkanes have largely replaced Freons as propellants in aerosol cans?
A.
B.
C.
D.
E.
30.  Which of the following is true for the initiation step of a free radical chloroniation reaction?
A.
B.
C.
D.
E.
31.  The bond dissociation energy is the amount of energy required to break a bond_____.
A.
B.
C.
D.
E.
32.  Which of the following alkyl chlorides is most likely to undergo rearrangement during a solvolysis reaction?
33.  Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide?
34.  Which of the following statements correctly pertains to a pair of enatiomers?
35.  WWhich of the following reactive intermediates can best be descibed as both nucleophilic and strongly basic?
36.  Among the following alkyl halides, choose the one with the lowest boiling point.
37.  Which of the following alkyl halides is most likely to undergo rearrangement in an SN1 reaction?
38.  Which of the following correctly lists the conformations of cyclohexane in order of increasing energy?
A.
B.
C.
D.
E.
39.  The major monobrominated product which results when ethylcyclohexane is subjected to free radical bromination is:
40.  Which of the following reactive intermediate species maintains sp3 hybridization?
41.  Which of the following alkyl halides is most likely to undergo rearrangement in an SN1 reaction?
42.  Which of the following statements is(are) true for the compound (3R, 4R)-3,4-dimethylhexane?
A.
B.
C.
D.
E.
43.  When one compares the densities of n-hexane and water, one finds:
44.  Energy is _______ when bonds are formed and is _____when bonds are broken; therefore, bond dissociation energies are always________.
45.  How many carbons do the primary alkane constituents of gasoline contain?
A.
B.
C.
D.
E.
46.  What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and (2R,3R,4R)-2,3,4-trichloroheptane?
47.  Which is a measure of the randomness of a systems?
48.  ______ is the study of reaction rates.
49.  Which of the following statements is the best statement of the Hammond Postulate?
50.  Which of the functional groups below contain a hydroxyl group as a part of their structure?
51.  Which of the following compounds is the most nucleophilic?
52.  Dehydrohalogenation of an alkyl halide by treated it with a strong base to yield an alkene product typically occurs by what reaction mechanism?
53.  Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?I.    Rate= k[base]II.   Rate= k[base][RX]III.  Rate= k[RX]IV. The reactions occur in twwo or more distinct steps.V.  Rearrangements are sometimes seen.     A) III and V           B) II and IV           C) I,IV, and V          D) I only      E) III,IV, and V
54.  In the first propagation step of the free radical chlorination of methane, which of the following occurs?
A.
B.
C.
D.
E.
55.  Which of the following best describes DDT?
A.
B.
C.
D.
E.
56.  Which of the following correctly expresses the standard Gibbs free energy change of reaction in terms of the reaction temperature (T) and equilibrium constant (K)?  
57.  Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?
A.
B.
C.
D.
58.  Which of the following functional groups does not have at least one sp2 hybridized carbon atom as a constituent of the group?
59.  Which of the following statements applies to the E2 mechanism?
60.  Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?
61.  Which of the following is a carbene?
A.
B.
C.
D.
E.
62.  Which of the following reactive intermediates can best be descibed as both nucleophilic and strongly basic?
A.
B.
C.
D.
E.
63.  When ioniztion occurs at the single sterocenter of a chiral compound, the resulting carbocation is:
A.
B.
C.
D.
E.
64.  What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichlorheptane and (2S,3S,4R)-2,3,4- trichloroheptane?
65.  Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per methylene?
66.  What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans- 1,3-dimethylcyclopentane?
A.
B.
C.
D.
E.
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