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Final Examination, Organic Chemistry 1 (CHEM 2210) December 2000 Version A
- What are the hybridization of, and the geometrical shape around, the nitrogen atom in the following molecule?
CH 3 O
N
CH 3
A. sp, linear B. sp, bent C. sp^2 , trigonal planar D. sp^2 , bent
- Which of the following compounds is a cis isomer?
A. B. C. D.
- The nitrogen atom in which of the following molecules/ions has the largest (positive) formal charge?
A. B. C. D.
CH 3 –N–CH 3
CH 3
CH 3 –N–CH 3 (CH 3 ) 4 N CH 3 –C≡N :
- Which of the following compounds is NOT a structural isomer of cyclohexanol?
OH
OH
OH
O
A. B. C. D.
- What class of compounds does the following structure belong to?
O
O
A. Ketone B. Ether C. Ester D. Aldehyde
- How many sigma bonds are present in the following molecule?
OH
A. 11 B. 12 C. 17 D. 18
- What is the direction of the dipole moment in the molecule whose structure is shown below?
C N OH
H 3 C
H 3 C
A. B. C. D.
- Which of the following functional groups is NOT present in the following molecule?
O
O
OH
A. 2˚ alcohol B. Alkene C. Ester D. Ether
- What is the name of the following compound?
A. 1-ethyl-8-methylbicyclo[4.3.0]nonane B. 1-ethyl-3-methylbicyclo[4.3.0]nonane C. 5-ethyl-3-methylbicyclo[4.3.0]nonane D. 3-ethyl-1-methylbicyclo[4.3.0]nonane
- Which of the following shows 1-bromo-2-iodoethane in its most stable conformation?
C C
H
Br H
I
H
H
C C
Br
H H
H
I
H C. D.
C C
Br
H H
H
H
I
A. C C
H
Br H
H
H
I
B.
- What is the name of the following compound?
Br
CH 3
C
HO
CH CH 2
A. cis- 3-bromo-1-buten-3-ol B. (S)-2-bromo-3-buten-2-ol C. (R)-2-bromo-3-buten-2-ol D. cis- (R)-2-bromo-3-buten-2-ol
- How many stereoisomers does the given compound have?
Br
CH 3
Br
A. 2 B. 4 C. 8 D. 16
- Which of the following is true about the following reaction?
H C OCH 3
CH 2 Cl
CH 3
Zn, HCl
A. The product will have R configuration. B. A meso compound is produced. C. The product will have S configuration. D. The product is not optically active.
- Consider the structure shown.
C 6 H 5
H OH
H
H 3 C
NH
CH 3
Ephedrin, I
Which of these Fischer projection formulas corresponds to I?
C 6 H 5 C^6 H^5
H
H
OH
CH 3
NHCH 3
H
H
OH
NHCH 3
CH 3
C 6 H 5 C^6 H^5
HO H
CH 3 HN CH 3
H
HO H
CH 3 NHCH 3
H
A. B.
C. D.
- Which of the following alkenes is a Z diastereomer?
C. D.
A. B.
- Which of these alkenes has the GREATEST heat of hydrogenation?
A. B. C. D.
- Which of the following reagents will complete the reaction shown?
A. KOH B.H 2 SO 4 C. Ni 2 B D. NaNH 2
+ _________
Br
Cl ?
- The index of hydrogen deficiency of C 14 H 20 is...
A. 20 B. 4 C. 5 D. 6
- The alkene that is the major product of the following dehydration reaction is:
heat
H 3 PO 4
H 3 C
H 3 C OH
CH CHCH 3
A. disubstituted, cis B. disubstituted, trans C. trisubstituted D. tetrasubstituted
- What is the correct name for the following compound?
Cl
A. (Z)-2-chloro-4-methyl-2-pentene B. (E)-2-chloro-4-methyl-2-pentene C. (Z)-4-chloro-2-methyl-3-pentene D. (E)-4-chloro-2-methyl-3-pentene
- Dehydrohalogenation reactions usually give the most stable alkene as their major product when more than one product is possible. An exception to this rule occurs when which of the following reagents is employed as the base?
A. potassium tert -butoxide B. sodium amide C. potassium hydroxide D. nickel boride
- Which of the following alcohols will dehydrate most rapidly with sulfuric acid and heat?
OH
OH
OH
OH
A. B. C. D.
- What is the major organic product of the following reaction?
A. B.
C. D.
H 3 CC CH
2 mol HBr
BrCH 2 CH 2 CH 2 Br BrCH 2 CHBrCH 3
CH 3 CH 2 CHBr 2 CH 3 CBr 2 CH 3
- What is the major organic product of the following reaction?
OH
OH
D.
OH
OH
C.
B. O
COOH
COOH
A.
C 6 H 5 CO 3 H
- What is the major organic product of the reaction shown?
HBr
no pe roxides
A. CH 3 CH 2 CH 2 CH 2 CH 2 Br B. CH 3 CH 2 CH(Br)CH=CH 2 C. CH 3 CH 2 CH 2 CH(Br)CH 3 D. CH 3 CH 2 CH 2 CH(Br)CH 2 Br
- Which of these reagents CANNOT be used to distinguish between cyclohexane and cyclohexene?
A. Br 2 /CCl 4 B. conc. H 2 SO 4 C. KMnO 4 D. NaOH
- What is the major organic product of the reaction shown?
CH 3
CH 3
OH
CH 3 OH CH 3
OH
OH CH 3
BH 3 • THF H 2 O 2 , OH
A. B. C. D.
- Which of these is the best way to synthesize the ether shown?
O
CH 3
A. OH^ +^ CH 3 OH^ B.^ O
C. I + CH 3 O-^ D. OH + CH 3 I
- Which of the following acid-base reactions does not occur?
+C 6 H 5 COOH
_
A. OH
+ C 2 H 6
_
C. OH
+ H 2 O
_
B. CH 3 CH 2
+ C 6 H 5 NH 2
_
D. CH 3
- When is oxymercuration-demercuration the preferred method for the synthesis of an alcohol from an alkene?
A. When the chemist wants the anti-Markovnikov product. B. When the chemist wants a Markovnikov product with carbocation rearrangements. C. When the chemist wants an anti-Markovnikov product with no rearrangement. D. When the chemist wants a Markovnikov product with no rearrangements.
- Which of the following is an initiation step?
B. Br 2 heat^ 2Br
C.
D. (^) Br
A. CH 3 + HBr CH 3 Br + Br
- Which of the following reactions has an Eact = 0?
A. (^) Br (^) + (^) Br (^) Br 2
B. Br 2 Br^ + (^) Br
light
C. (^) Br + (^) CH 4 HBr + CH 3
D. CH 3 + CH
3 CH^3 CH 4 + CH 3 CH 2
- How many hydrogen atoms are there in the compound shown?
Cl
O
A. 13 B. 14 C. 15 D. 16
- The reaction of 1-butene with HBr in the presence of peroxides yields 1-bromobutane. The mechanism for the reaction involves:
A. attack on the alkene by a bromine atom, Br.. B. attack on the alkene by a hydrogen atom, H.. C. attack on the alkene by a Br+^ ion. D. attack on the alkene by a H+^ ion.
