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Material Type: Exam; Professor: Keller; Class: Organc Chem I; Subject: Chemistry; University: Florida International University; Term: Fall 2011;
Typology: Exams
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Department of Chemistry & Biochemistry
CHM 2210-U01 – ORGANIC CHEMISTRY I
Fall 2011
Dr. Keller/Dr. Landrum
Version 2
Look over the Written Questions early during your test to be sure you allocate your time appropriately.
A)
Br
B) Br
H
D)
NH 2
C)
Br (^) NaNH 2 Excess Br^ Work-up
NH 4 Cl
CH 3
D
C
E) Na
A) B)
C) (^) D)
E) All are Equally stable
CH (^3)
D
H
Br
CH (^3)
D
Br
H
H
D
CH (^3)
Br
Br
D
CH (^3)
H
A) B)
C) (^) D)
E) Both B and D would be produced
CH 3
OH
OH
CH (^3)
OH
CH (^3)
OH
CH (^3)
OH CH (^3)
OH
OH
A) (^) B)
C) (^) D)
E)
A)
B)
C)
D) E)
X (C 8 H 14 )
H 2
Pt
Y (C 8 H 16 )
OH OH
OH
OH
OH
A) B)
B) D)
E)
A. Br -^ is too poor a leaving group. B. The substrate is too hindered. C. Too much angle strain would be present in the alkene product. D. Sodium ethoxide is a poor base to use in E reactions. E. The C-H and C-Br bonds which need to break cannot achieve anti-periplanar orientation.
A. 2-Pentyne + 2H 2 /Pt pentane B. 2-Pentyne + H 2 /Ni 2 B(P-2) Z-2-Pentene C. 2-Pentyne + Li/NH 3 (l) E-2-Pentene D. All of the above are correct. E. None of the above is correct.
A. no rings and no double bonds. B. no rings and one double bond. C. one ring and one double bond. D. two rings and no double bonds. E. one triple bond.
A. rearrange to form a more stable carbocation. B. lose a proton to form an alkene. C. combine with a nucleophile. D. all of the above.
A) B)
C) D)
E) None of the Above
OH Con H 2 SO^4
A) A)
C) D)
E)
H
NaNH 2 CH 3 CH 2 Br^ H (^2) Ni 2 B (P-2) X
Br
A) B)
C) (^) D)
E)
A. Overall, the process results in syn addition and anti -Markovnikov orientation. B. Overall, the process results in anti addition and anti -Markovnikov orientation. C. Overall, the process results in syn addition and Markovnikov orientation. D. Overall, the process results in anti addition and Markovnikov orientation. E. The stereochemistry and orientation are unpredictable.
A. (E)-4-ethyl-2,5-dimethyl-3-octene B. (Z)-4-ethyl-2,5-dimethyl-3-octene C. (E)-5-ethyl-4,7-dimethyl-5-octene D. (E)-4-ethyl-2,5-dimethyl-4-octene E. (Z)-5-ethyl-4,7-dimethyl-5-octene
A. 2,2-Dimethyl-2-hexene B. 2,3-Dimethyl-2-hexene C. 2,4-Dimethyl-2-hexene D. 2,4,4-Trimethyl-2-pentene E. More than one of the above is a possible answer
A) B)
C) D)
E)
O
O
H
H
H
Br
Br
H
H
Br
H
Br
H
Br
H
Br
I) II) III)
OH
Br
Br
OH
Br
Br
OH
Br
OH
OH
A) (^) B) C)
D) E)
C
Cl
Cl
What is the structure of the alkene?
A. I only B. II and III C. II only D.. III only E. I, II, and III
A. Reaction with H 3 O+^ , H 2 O B. Reaction with Br 2 , CCl (^4) C. Reaction with Cl 2 , CCl (^4) D. Reaction with cold, dilute KMnO 4
A. the product is statistically favored. B. steric hindrance favors its formation. C. it is formed via the more/most stable carbocation. D. it is the more/most rapidly produced product. E. All of the above are reasons.
A. Hydroboration/oxidation B. Bromination C. Hydroxylation with cold KMnO 4 D. Hydrogenation E. Hydrochlorination (addition of HCl)
Hg(OAc) 2 /H 2 O
NaBH 4
OH
Br 2
Br
Br
KMnO 4 Cold, 0 C
OH
OH D
D
H H
D 2 /Pt
A)
B)
C)
D)
O
OH
O
O (^) O Mn O O
OH (^) OH
OH (^) OH OH^ OH
A)
B)
C)
D) E)
dil. KMnO (^4)
cold
?
