Survey of Organic Chem Exam 2

Survey of Organic Chem Exam 2 - COM 11 ED4 PR EM P PRE MED...

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Unformatted text preview: COM 11. ED4 - PR EM P PRE MED 411 .CO .CO 411 MED MPRE .CO 411 MED MPRE .CO 411 MED MPRE Answers: 1 B 2 C 3 D 4 C 5 D 6 D 7 B 8 A 9 E MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM Practice Exam II Survey of Organic Chemistry Dr. Landrum ‐Fall 2008 Name Panther ID # Select the best answer for each question. There is only a single best answer to each question. 10 11 12 13 14 15 16 17 18 19 B D D B D D B B D C 20 21 22 23 24 25 26 27 28 29 C C E E E B B D C E COM 11. ED4 - PR EM PRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 1. How is the compound shown classified? A) a primary alkyl halide B) a primary alcohol C) a secondary alkyl halide D) a secondary alcohol HO E) a tertiary alkyl halide 2. How is the compound shown classified? A) a quaternary ammonium ion B) a quaternary amine C) a secondary amine N D) a primary amine E) a tertiary amine H 3. How is the compound shown classified? A) a secondary alkyl halide B) a primary alkyl halide C) a quaternary alkyl halide D) a tertiary alkyl halide Cl E) a tertiary alcohol 4. How is the compound shown classified? O A) an aldehyde B) a ketone OH C) a carboxylic acid D) an ester E) an amide 5. What type of intermolecular interactions are there between molecules of (CH3CH2)2O ? A) induced dipole‐induced dipole B) dipole‐dipole C) hydrogen bonding D) A and B E) A, B, and C 6. Which of the following is the LEAST soluble in H2O? A) CH3OCH3 B) CH3CH2OH C) CH3CO2H D) CH3CH2CH3 E) CH3CHO COM 11. ED4 - PR EM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 7) Which of the following is the staggered conformation for rotation about the C2‐C3 bond in the following structure? CH3 C2H5 H H H H H H3C H H H H 3C CH3 H CH3 H CH3 CH3 III. I. II. A) I B) II H3C H C2H5H C) III C2H5 CH3 D) IV H H H 3C CH3 H3C H E) V PRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM IV. V. 8) Which of the following describes the MOST stable conformation of cis‐1‐tert‐butyl‐3‐ methylcyclohexane? A) Both groups are equatorial. B) Both groups are axial. C) The tert‐butyl group is equatorial. D) The tert‐butyl group is axial and the methyl group is equatorial. E) none of the above 9) Which of the following has one equatorial and one axial alkyl substituent in its MOST stable conformation? A) 1,1‐dimethylcyclohexane B) cis‐1,2‐dimethylcyclohexane C) cis‐1,3‐diethylcyclohexane D) cis‐1,4‐diethylcyclohexane E) both B and D 10) Which of the following is a propagation step for the monobromination of cyclohexane? A) I B) II C) III D) IV E) V COM 11. ED4 - PR EM PRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 11) How many dichlorinated products can be isolated when 2,3‐dimethylbutane reacts with Cl2/hv? (consider only constitutional isomers; i.e. ignore stereosiomers) CH3 A) 3 B) 4 H3C CH C) 5 D) 6 H3C CH E) 7 CH3 12) How many monochlorinated products would be obtained from methylcyclobutane? (consider only constitutional isomers; i.e. ignore stereosiomers) A) 1 B) 2 C) 3 D) 4 E) 5 13) Which of the following reactions is the initiation step in the free radical chlorination of methane? A) Cl2 + Cl ∙ → Cl ∙ + Cl2 B) Cl2 → 2 Cl ∙ C) ∙ CH3 + Cl ∙ → CH3Cl D) CH4 + Cl ∙ → HCl + ∙ CH3 14) Which of the following is NOT a step in the free radical chlorination of methane? A) CH4 + Cl ∙ → ∙ CH3 + HCl B) Cl2 → 2 Cl ∙ C) Cl ∙ + ∙ CH3 → CH3Cl D) ∙ CH3 + CH4 → CH4 + ∙CH3 15) Which of the following occurs in the initiation step in the free radical bromination of ethane to form bromoethane? A) a C‐H bond breaks B) a Br‐H bond forms C) a C‐Br bond forms D) a Br‐Br bond breaks E) a C‐C bond breaks COM 11. ED4 - PR EM PRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 16) Rank the free radicals (I‐III) shown below in order of decreasing stability (i.e., from MOST stable to LEAST stable, Left to Right). CH3 A) I > III > II CH2 CH3 H2C CH B) II > III > I H2C CH H 2C C C) I > II > III HC CH2 H2C CH2 H2C CH2 D) II > I > III E) III > II > I I. II. III. 17) How many distinct monochlorinated products result when the alkane below is reacted in the presence of light and Cl2? (ignore stereoisomers) A) 3 B) 4 C) 5 D) 6 E) 7 18) The following molecule contains how many 1° hydrogens? A) 2 B) 4 C) 6 D) 12 E) None of these 19) The major monobrominated product which results when 1,4‐dimethylcyclohexane is subjected to free radical bromination is: A) a primary bromide. B) a secondary bromide. C) a tertiary bromide. D) a quaternary bromide. E) bromomethane. 20) Which of the halogens below does not undergo free radical halogenation with ethane? A) fluorine B) chlorine C) iodine D) bromine E) All of the Halogens react COM 11. ED4 - PR EM PRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 21) Which of the following most nearly describes the hybridization of the methyl radical? A) tetrahedral, sp3 B) trigonal pyramidal, sp3 C) trigonal planar , sp2 D) bent, sp2 E) linear , sp 22) What is the IUPAC name for the following compound? A) 1,2‐cyclobutene B) dicyclobutene C) 1,2‐cyclobutadiene D) cis‐dicyclobutene E) 1,3‐cyclobutadiene 23) What is the IUPAC name of the compound shown? A) 1‐chloro1ethyl‐1‐ethene B) trans‐2‐chloro‐1‐butene C) cis‐2‐chloro‐1‐butene D) (Z)‐1‐chloro‐1‐butene Cl E) 2‐chloro‐1‐butene 24) What is the IUPAC name of A) 1‐methyl‐1‐pentene B) 1‐methyl‐2‐cyclopentene C) trans ‐1‐methylcyclopentene D) cis ‐2‐methylcyclopentene E) 1‐methyl‐2‐cyclopentene 25) Provide the proper IUPAC name for the alkene shown below. A) 3,5,7‐trimethyl‐2‐cycloheptene H3C B) 3‐methyl‐5,7‐diethylcycloheptene C) 3,5‐dimethyl‐7‐ethylcycloheptene C2H5 D) 3,5‐dimethyl‐7‐ethylcycloheptene E) 3,5‐dimethyl‐7‐ethylcycloheptene C2H5 26) Which of the following best describes the geometry about the carbon‐carbon double bond in the alkene below? A) E Cl Br B) Z C) neither E nor Z D) cis E) trans Cl COM 11. ED4 - PR EM PRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 27) Which of the following is the MOST stable alkene? A) B) C) D) E) 28) Which of the following is listed in the correct order of priority? (lowest to highest, left to right) A) ‐ ‐I < ‐Br < ‐Cl < ‐F < ‐H B) ‐H < ‐F < ‐C < ‐O < ‐S C) ‐H <‐C < ‐N < ‐O < ‐S D) ‐S < ‐O < ‐C < ‐N < ‐ Cl E) None of the above 29) Which of the following is listed in the correct order of priority? (lowest to highest, left to right) A) ‐ ‐C2H5 < ‐CH3 < ‐C(CH3)3 < ‐CH2CO2H< ‐CH2CHO B) ‐CH3 < ‐C2H5 < ‐ CHO < ‐CH2CH2OH< ‐C(CH3)3 ‐ C) CHO < ‐CH2OH < ‐C(CH3)3 < ‐C2H5 < ‐CH3 D) ‐CH3 < ‐C2H5 < ‐C(CH3)3 < ‐CH2CO2H< ‐CH2CHO E) ‐CH3 < ‐C2H5 < ‐C(CH3)3 < ‐CH2OH< ‐CHO COM 11. ED4 - PR EM 11. ED4 COM Exam II – Supplement 10pts Name Panther ID # ED4 11. COM - PR EM COM - PR EM 11. A. Draw trans‐1,3‐dibromocyclohexane in the its MOST stable chair conformation 11. COM - PR EM ED4 11. COM - PR EM ED4 PRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 B. Draw the structure of 3Z‐5‐isopropyl ‐2‐methyl‐1,3‐decadiene (show all hydrogens) ...
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