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Organic Chem Practice Exam by Solomon CH 1-4
Organic Chem Practice Exam by Solomon CH 1-4
Organic Chem Practice Exam by Solomon CH 1-4
Name: _______________________________________________ 1. An alkane that can exhibit optical activity is a. Neopentane b. Isopentane c. 3-Methylpentane d. 3-Methylhexane e. 2,3-Dimethylbutane 2. Which of the following is a representation of (R)-2-butanol?
H H3C OH CH2CH3 H CH3 OH CH2CH3 HO H CH3 CH2CH3 HO CH3 H CH2CH3 H CH2CH3 OH CH3
I
a. III, IV
II
III
IV
3. Which of the following numbered compounds is the enantiomer of the molecule immediately below?
H H Br CH3
H Br H CH3 H
CH3 Br H H
CH3 H Br
II
III
a. I b. II c. III d. II & III e. None of the above 4. How many discrete1 dimethylcyclopropanes are there? a. 2 b. 3 c. 4 d. 5 e. 6 5. Below is shown the Fischer projection of one of the enantiomers of lactic acid. Using the Cahn-Ingold-Prelog system, what is the absolute configuration of the form shown? You must show your work for credit
O HO OH H
L-(-)-lactic acid
6. A biological reduction of pyruvic acid to lactic acid generates a mixture with a specific rotation of -2.25o. What is the enantiomeric excess of the mixture, given the specific rotation of L-(-)-lactic acid is -2.50o?
Answer: _________________________________________________ 7. The specific rotation of L-(-)-lactic acid is -2.50o. If a sample of lactic acid showed a specific rotation of +2.00o, what would the percent composition of the lactic acid mixture be?
II
III
IV
a. I b. II c. III d. IV e. Two of the above 9. Please completely name the following compound using IUPAC nomenclature rules
Name: ______________________________________________________ 10. Please completely name the following compound according to IUPAC rules
O OH OH
Name: ______________________________________________________ 11. Please completely name the following compound according to IUPAC rules
H3C
CH 3
OH H H
I
a. Constitutional isomers b. Enantiomers c. Identical d. Diastereomers e. Not isomeric
II
OH
O Cl
Cl I
a. Constitutional isomers b. Enantiomers c. Identical d. Diastereomers e. Not isomeric
OH II
SCH3 CHO
H H Me SCH3 Et CHO II
e. Not isomeric
16. Which is a true statement concerning the transition state of the rate determining step of an SN1 reaction? a. Structurally, it closely resembles the carbocation intermediate b. Both covalent bond breaking and bond making are occurring c. Formation of the transition state is an exothermic reaction d. The transition state has zero overall charge e. More than one of the above 17. Elimination reactions are favored over nucleophilic substitution reactions when a. high temperatures are used b. t-butoxide is used c. 3o alkyl halides are substrates d. the nucleophile is a strong base and the substrate is a 2o alkyl halide e. any of the above occurs 18. Which of the following would you expect to be the principal product(s) when
HC
C:
Na
II
III
HC
CH
IV
a. I b. II c. III d. IV
a. HOb. H2O c. TsOd. MsOe. CH3O20. Which would be the principal product(s) of the following reaction?
O O S
CF3 O
NaN3 DMF
N3
N3
I
a. I b. II c. III d. IV e. None of the above
II
III
IV
1. NaI, acetone
Cl
2. CH3CO2Na, CH3CO2H
a.
b.
c.
d.
22. The products for the following would be primarily dictated by which mechanism?
Br
CH3SNa EtOH
CH3OH 55oC
CH3 OCH3
I
CH3 CH3
II
CH3
CH2
III
IV
a. I b. II c. III d. IV e. All of the above 24. Which would be the principal product(s) of the following reaction?
H3C H CH3 Br
H3C H
CH3 OCH3
H3C H
OCH3 CH3
II
H3C
CH3
H3C
III
IV
e. All of the above 25. Which would be the principal product(s) of the following reaction?
CH3 Br CH3 CH3
O O
O O
II
III
IV
a.
OH
b.
OC2H5
c.
d.
CH3CH2OH
Br
25 oC
OCH2CH3
OCH2CH3
II
III
IV
a. I b. II c. III d. IV e. None of the above 28. The products for the following would be primarily dictated by which mechanism?
O O S
CF3 O
CH3CH2OH
70 oC
OCH(CH3)2 OCH(CH3)2
II
III
IV
a. I b. II c. III d. IV e. None of the above 30. Please synthesize dipropyl ether beginning with any starting materials 3 carbons or less
31. Please synthesize 1,4-dioxan beginning with any starting materials 3 carbons or less