Hyperlearning MCAT Instructor Qualifying Exam Organic Chemistry

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1 Hyperlearning MCAT Instructor Qualifying Exam Organic Chemistry 30 Questions (5 pages); Time limit = 45 minutes Use of books or notes is not permitted. 1. When analyzed with a polarimeter, which of the following would shown a nonzero optical rotation? A. A meso compound B. A racemic mixture C. An achiral compound D. A diastereomeric mixture 2. Any compound with 3 stereocenters must have: A. 1 enantiomer, 6 diastereomers, 3 epimers B. 1 enantiomer, 8 diastereomers, 3 epimers C. 1 enantiomer, 4 diastereomers, 1 epimer D. 1 enantiomer, 6 diastereomers, 1 epimer 3. How many different monochlorinated compounds would be produced from the free-radical chlorination of n-pentane? A. 1 B. 2 C. 3 D Which of the following reagents would most effectively convert a primary alcohol into the corresponding primary alkyl halide? A. NaBr B. CH 3 I C. Cl 2 / hν D. PCl 3 5. In deciding whether a substrate will undergo an S N 1 or an S N 2 reaction, all of the following must be considered EXCEPT the: A. degree of substitution of the carbon atom bonded to the leaving group. B. leaving group ability. C. basicity of the incoming group. D. solvent. E. nucleophilicity of the incoming group. 1

2 6. What is the reaction mechanism by which 1-bromo-3,5,6-trimethylheptane reacts with sodium thiomethoxide to form a thioester? A. S N 1 B. S N 2 C. E1 D. E2 E. Electrophilic aromatic substitution 7. Elimination of H-Br from 3-bromo-4-methylheptane can occur to give several different products. The most thermodynamically stable possible product is: A. 4-methylheptene B. 4-methylhept-2-ene. C. 4-methylhept-3-ene. D. 4-methylhept-4-ene. E. 4-methyleneheptane. 8. Elimination reactions can be favored over substitution reactions by all of the following EXCEPT: A. use of a strong base. B. heat. C. use of a poor nucleophile. D. use of a good leaving group. 9. Alcohols have higher boiling points than might be expected due to: A. the Woodward Hoffman rules. B. the Cahn Ingold Prelog rules. C. the Thorpe Ingold effect. D. the anomeric effect. E. hydrogen bonding. 10. The oxidation of alcohols by pyridinium chlorochromate can form two different products, depending on whether water is present. These two products are: A. a peroxide and an aldehyde. B. a peroxide and a carboxylic acid. C. a carboxylic acid and a ketone. D. a ketone and an aldehyde. E. a carboxylic acid and an aldehyde. 11. Which one of the following types of reaction conditions are ethers NOT stable to? A. Oxidation B. Reduction C. Strong acid D. Strong base 12. When an unsaturated hydrocarbon is reduced to an alkane by addition of molecular hydrogen in the presence of a metal catalyst, the reaction is called: A. hydrolysis. B. hydroformylation. C. hydration. D. hydrogenation. 2

3 13. The intermediate formed upon addition of molecular bromine to propene is A. the more substituted Markovnikov carbocation. B. the less substituted anti-markovnikov carbocation. C. the less substituted Markovnikov carbocation. D. a bromonium ion. 14. Hydroboration oxidation of an olefin converts the alkene into the: A. Markovnikov alcohol. B. anti-markovnikov alcohol. C. epoxide. D. anti-markovnikov ketone. 15. All of the following are true of an aromatic compound EXCEPT: A. there must be 4n + 2 electrons in the π system. B. the compound must be cyclic. C. the compound must have a p orbital on every atom of the ring available for π bonding. D. all atoms in the ring must be carbon atoms. 16. In a Friedel Crafts alkylation reaction of toluene, the tolune acts as: A. a nucleophile. B. an electrophile. C. an amphiphile. D. a leaving group. 17. Addition of ethylene glycol to acetaldehyde will form a: A. hemiketal. B. hydrate. C. cyclic acetal. D. Schiff base. 18. Addition of methylamine to propanal followed by heating will produce an: A. amine. B. amide. C. imide. D. imine. 19. The product of an aldol condensation is: A. an α,β-unsaturated carbonyl compound. B. a 1,3-dicarbonyl compound. C. a 1,5-dicarbonyl compound. D. a 1,3-diol compound. 20. If the ester group of ethylacetoacetate were hydrolyzed to give the corresponding β-ketoacid, subsequent heating would form a new organic compound and: A. H 2 O. B. CO 2. C. HCl. D. CO. 3

4 21. Treatment of tristearin (a triester) with base and heat induces ester hydrolysis to form which of the following? I. Alcohols II. Carboxylic acids III. CO A. I only B. II only C. I and II only D. I, II, and III 22. Esters can be synthesized by the addition of the appropriate alkoxide to the appropriate acid halide. In this reaction, the first two mechanistic steps are: A. nucleophilic addition / elimination. B. nucleophilic addition / substitution. C. electrophilic addition / elimination. D. electrophilic addition / substitution. 23. Of the following carboxylic acid derivatives, which one is LEAST reactive toward nucleophilic addition? A. Ester B. Amide C. Acid halide D. Acid E. Acid anhydride 24. In a given ether solution containing a phenol, an amine, and a complex neutral organic molecule, the phenol can most easily be extracted from the mixture by using: A. a neutral aqueous extraction solvent. B. an acidic aqueous extraction solvent. C. a basic aqueous extraction solvent. D. sodium sulfate. 25. In a Diels Alder reaction between ethyne and 1,3-butadiene, the product is: A. 1-cyclohexene. B. 1,2-cyclohexadiene. C. 1,3-cyclohexadiene. D. 1,4-cyclohexadiene. 26. The progress of the following oxidation reaction can easily be monitored by infrared spectroscopy: Alcohol / (oxidant) Aldehyde. In what region of the IR spectrum does the carbonyl stretch of the aldehyde appear? A. Around 3400 cm 1 B. Around 2100 cm 1 C. Around 1700 cm 1 D. Around 1200 cm 1 4

5 27. A compound has the following 1 H NMR spectrum: δ 2.5 (1H, t, J = 3 Hz); 3.1 (1H, s); 4.3 (2H, d, J = 3 Hz) ppm. The 1 H NMR resonance at 4.3 ppm corresponds to protons that are coupled to how many other protons? A. 0 B. 1 C. 2 D Which of the following most likely describes the pk a of the ammonium group of a zwitterionic amino acid? A. pk a < 2 B. 2 < pk a < 4 C. 4 < pk a < 10 D. 10 < pk a 29. What type of bond links amino acids together in a protein? A. Ionic bond B. Glycosidic linkage C. π bond D. Peptide bond 30. The monosaccharide D-arabinose is an aldopentose. How many carbon atoms are in D-arabinose? A. 2 B. 3 C. 4 D. 5 E. 6 END OF EXAM 5

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