MCAT Review Test Exam 1 (1999)

1st Semester O-Chem Practice Final Exam (2011)

I. Nomenclature

1. The correct name for the compound shown below is:

a. cis-3-bromo-2,4-hexadiene.

b. (2Z, 3Z, 4E)-3-bromo-2,4-hexadiene.

c. (2E,4E)-3-bromo-2,4-hexadiene.

d. (E,Z,E)-3-bromo-2,4-hexadiene.

e. (2Z,4E)-3-bromo-2,4-hexadiene.

2. What is the correct name for:

a. 3-methylbromopentane

b. 3-bromomethylcyclohexane

c. cis-bromomethylcyclopentane

d. cis-1-bromo-3-methylcyclopentane

e. 1-bromo-3-methylcyclopentane3. Choose the correct name for:

a. Z-3-chloro-2-pentene

b. Z-2-chloro-1-methylbutene

c. trans-3-chloro-2-pentene

d. E-3-chloro-2-pentene

e. none of the above

4. Which molecule is an amide?

a. CH3CH(NH2)CO2Hb. (CH3)2CHC(NH)CH3c. CH3NHCH2OOH

d. CH3NHCOCH3e. none of these are amides

5. Which molecule is a carboxylic acid?

a. CH3CH(NH2)CO2Hb. (CH3)2CHC(NH)OCH3c. CH3NHCH2OOH

d. CH3NHCOCH3e. none of these are carboxylic acids

6. Which molecule would be most soluble in hexane?

a. CH3CH(NH2)CO2Hb. (CH3)2CHCN

c. (CH3)2NCH2OH

d. CH3NHCOCH3e. H2O7. The number of degrees of unsaturation in 2-pentyn-1-ol is:

a. 1b. 2c. 3d. 4e. can not be determined

8. How many tertiary H's in 2-bromo-3-methylcyclohexanone (shown below)?

a. 0

b. 1

c. 2

d. 4

e. 12

II. Stereochemistry

9. What property does trans-1,3-dimethylcyclobutane have that makes its mirror image superimposable?

a. limited solubility in non-polar solvents.

b. a low boiling point.

c. a plane of symmetry.

d. trans relationship of substituents.

e. a four member ring.

10. Which of the following compounds has an R configuration?

e. none of the above

11. Which molecule has the most thermodynamically acidic hydrogen?

12. Consider the products expected from the reaction shown. Which of the following statements is true?

a. Only 2 products will be formed.

b. Only one stereoisomer will be formed.

c. A racemic mixture of one alcohol is formed.

d. The products will be racemic.

e. The product will be a ketone.

13. Which is a pair of conformers?

III. Reactions and Mechanisms

14. Which is the correct Fischer projection for (R)-2-bromobutane?

15. What's the best way to carry out the reaction shown?

a.Add TsCl and then H2SO4 and heat.

b.Add Br2 in NaOH and then dehydrohalogenate.

c.Add KOH and heat.

d. Add H2SO4 and heat.

e.Can't be done with modern organic chemistry.

16. What is the product (A) formed in the sequence shown below?

a.

b.

c.

d.

e. I've forgotten too much organic chemistry to be able to answer.

17. What reagents would you use to carry out the following transformation:

18. Which is the best way to make:

a.

b.

c.

d.

e.

19. The best way to make the compound shown below from cyclopentene is:

a. B2H6 then H2O2, NaOH

b. 2 equivalents of acid and water

c. hot KMnO4

d. OsO4 then water

e. peracid followed by aqueous acid

20. Which of the following monomers gives the polymer shown below?

21. Which structure is an intermediate bromonium ion?

22. Which is the correct order of the following compounds A-D according to base strength (i.e. strongest base first)?

a. C>B>A>D b. C>A>B>Dc. A>C>D>B d. A>D>B>Ce. D>A>B>C

23. Determine the major product from the reaction shown.

24. The major product for the reaction shown below is:

a. 3-penten-2-ol b. 2-butene c. methanol d. 1-methoxy-2-butene e. 2-pentene

25. Which of the following is a termination step for a radical reaction?

a. R + O2

c. R + OOH

b. RH + O2

d. R + alkene

e. none of the above

26. How many signals will the proton NMR of 1,1-dichlorocyclopentane have?

a. 1

b. 2

c. 3

d. 4

e. 5

27. An alkene will react with electrophiles. A monosubstituted alkene will be

a. more acidic than a trisubstituted alkene.

b. less nucleophilic than a tetrasubstituted alkene.

c. less nucleophilic than a terminal alkyne.

d. more acidic than a terminal alkyne.

e. none of the above.

28. Predict the major final product for the following reaction:

29. Which of the carbocations is more stable and why?

a. A, because of hyperconjugation.

b. B, because it has less branching.

c. C, because resonance is more stabilizing than hyperconjugation.

d. A, because B and C are secondary carbocations and oxygen is electronegative.

e. They are all the same stability.

30. Alkyl halides can undergo elimination by the E1 or the E2 mechanism. Which of the following statements is true about the nature of the alkyl halide in these elimination reactions?

a. Both reaction paths follow the rate: 1 RX > 2 RX > 3 RX

b. E1 follows 3 RX > 2 RX > 1 RX and E2 follows 1 RX > 2 RX > 3 RX

c. E1 follows 1 RX > 2 RX > 3 RX and E2 follows 3 RX > 2 RX > 1 RX

d. Both reaction paths follow the rate: 3 RX > 2 RX > 1 RX

e. None of the above.