GRE Chemistry Domain 3: Organic Chemistry Welcome to your GRE Chemistry Domain 3: Organic Chemistry 1. GRE Chemistry: Organic Chemistry In organic chemistry, which reaction type involves the transition of an alkyl halide into an alkene? A. Nucleophilic substitution B. Electrophilic addition C. Dehydrohalogenation D. Hydrogenation None 2. GRE Chemistry: Organic Chemistry In an SN2 reaction, what is the effect of increasing the steric hindrance of the substrate? A. Increases the reaction rate B. Decreases the reaction rate C. Has no effect on the reaction rate D. Changes the reaction mechanism None 3. GRE Chemistry: Organic Chemistry Which type of isomerism is exhibited by compounds having the same molecular formula but different arrangements of atoms in space? A. Structural isomerism B. Conformational isomerism C. Stereoisomerism D. Tautomeric isomerism None 4. GRE Chemistry: Organic Chemistry In the Diels-Alder reaction, which of the following dienes is the most reactive? A. 1,3-butadiene B. Cyclopentadiene C. Isoprene D. 1,3-hexadiene None 5. GRE Chemistry: Organic Chemistry Which statement best describes the Hammond postulate? A. The transition state is more closely related to the reactants in endothermic reactions. B. The transition state is more closely related to the products in exothermic reactions. C. The transition state resembles neither the reactants nor the products. D. The transition state is a stable intermediate. None 6. GRE Chemistry: Organic Chemistry In the context of aromatic compounds, what is electrophilic aromatic substitution? A. The substitution of an aromatic hydrogen by an electrophile. B. The addition of an electrophile to an aromatic ring. C. The removal of an aromatic ring by an electrophile. D. The substitution of an aromatic ring by an electrophile. None 7. GRE Chemistry: Organic Chemistry What is the major product of the ozonolysis of 1-methylcyclohexene? A. 1-Methylcyclohexanol B. 1-Methylcyclohexanone C. Formaldehyde and 1-methylcyclohexanone D. Acetaldehyde and acetone None 8. GRE Chemistry: Organic Chemistry Which reaction mechanism is typically involved in the hydroboration-oxidation of alkenes? A. Electrophilic addition B. Free radical substitution C. Nucleophilic substitution D. Anti-Markovnikov addition None 9. GRE Chemistry: Organic Chemistry In organic synthesis, what role does a Grignard reagent typically play? A. Oxidizing agent B. Reducing agent C. Nucleophile D. Electrophile None 10. GRE Chemistry: Organic Chemistry In the context of organic reactions, what is the purpose of a protecting group? A. To increase the reactivity of a functional group. B. To isolate a specific region of a molecule. C. To prevent a functional group from reacting. D. To change the direction of a reaction. None 11. GRE Chemistry: Organic Chemistry What is the outcome of a Wittig reaction? A. Formation of an ester from an alcohol and a carboxylic acid. B. Formation of an amide from an amine and a carboxylic acid. C. Formation of an alkene from a carbonyl compound and a phosphonium ylide. D. Hydrolysis of an ester to produce an alcohol and a carboxylic acid. None 12. GRE Chemistry: Organic Chemistry What is the major organic product formed when cyclohexene is treated with N-bromosuccinimide (NBS) in the presence of light? A. 1-bromocyclohexene B. 3-bromocyclohexene C. 1,2-dibromocyclohexane D. Bromocyclohexane None 13. GRE Chemistry: Organic Chemistry What type of stereochemistry is observed in the products of the E2 elimination reaction? A. Cis stereochemistry B. Trans stereochemistry C. Racemic mixture D. No specific stereochemistry None 14. GRE Chemistry: Organic Chemistry In the Friedel-Crafts acylation reaction, what is the role of AlCl?? A. Nucleophile B. Base C. Catalyst D. Oxidizing agent None 15. GRE Chemistry: Organic Chemistry What is the product of the reaction of benzene with Cl? in the presence of FeCl?? A. Chlorobenzene B. Benzyl chloride C. Benzene hexachloride D. Dichlorobenzene None 16. GRE Chemistry: Organic Chemistry What is the outcome of the reaction between an aldehyde and a Grignard reagent followed by acid work-up? A. A secondary alcohol B. A tertiary alcohol C. A ketone D. An ester None 17. GRE Chemistry: Organic Chemistry What is the effect of increasing the temperature on the product distribution of the reaction between 2-methylbutane and chlorine under radical conditions? A. Increased formation of primary chlorinated product B. Increased formation of secondary chlorinated product C. Increased formation of tertiary chlorinated product D. No effect on the product distribution None 18. GRE Chemistry: Organic Chemistry In a Sharpless epoxidation reaction, what is the outcome when using L-(+)-diethyl tartrate? A. Formation of a trans-epoxide B. Formation of a cis-epoxide C. Enantioselective formation of the R-epoxide D. Enantioselective formation of the S-epoxide None 19. GRE Chemistry: Organic Chemistry What is the outcome of treating a vicinal diol with periodic acid (HIO?)? A. Oxidation to a ketone B. Formation of two aldehydes C. Cleavage to form an aldehyde and a ketone D. Formation of an acetal None 20. GRE Chemistry: Organic Chemistry In the Cannizzaro reaction, what is the outcome when formaldehyde is treated with concentrated NaOH? A. Formation of an alcohol and a carboxylic acid B. Formation of two molecules of alcohol C. Formation of a ketone D. No reaction None 21. GRE Chemistry: Organic Chemistry What is the major product in the Birch reduction of benzene? A. Cyclohexane B. 1,4-Cyclohexadiene C. Benzene D. 1,3-Cyclohexadiene None 22. GRE Chemistry: Organic Chemistry What is the major product of the ozonolysis of 1,3-cyclohexadiene followed by reduction with zinc in acetic acid? A. Cyclohexane B. 1,6-Hexanedial C. Cyclohexanone D. 1,4-Cyclohexanedione None 23. GRE Chemistry: Organic Chemistry In the Robinson annulation reaction, what types of compounds are generally involved? A. An aldehyde and a ketone B. Two aldehydes C. An aldehyde and an ester D. A ketone and an enone None 24. GRE Chemistry: Organic Chemistry What is the result of the Wittig reaction between benzaldehyde and methylidenetriphenylphosphorane? A. Benzyl alcohol B. Stilbene C. Benzoic acid D. Toluene None 25. GRE Chemistry: Organic Chemistry What is the major organic product when but-2-yne reacts with excess hydrogen in the presence of a Lindlar catalyst? A. But-2-ene (cis-isomer) B. But-2-ene (trans-isomer) C. Butane D. 1-Butene None 26. GRE Chemistry: Organic Chemistry In the context of carbon-carbon bond formation, what role does palladium play in a Suzuki coupling? A. Oxidizing agent B. Reducing agent C. Catalyst D. Solvent None 27. GRE Chemistry: Organic Chemistry What is the outcome of the reaction of an acyl chloride with a Gilman reagent (lithium diorganocopper)? A. Formation of a ketone B. Formation of an ester C. Formation of an aldehyde D. Formation of an alcohol None 28. GRE Chemistry: Organic Chemistry In the Baeyer-Villiger oxidation, what is the major product formed from cyclohexanone and peroxyacetic acid? A. ?-Caprolactone B. Cyclohexanol C. Adipic acid D. Cyclohexene oxide None 29. GRE Chemistry: Organic Chemistry Which reaction involves the conversion of an aldehyde or ketone into an imine? A. Wolff-Kishner reduction B. Clemmensen reduction C. Schiff base formation D. Grignard reaction None 30. GRE Chemistry: Organic Chemistry What is the major product of the ozonolysis of 1-methylcyclohexene? A. 1-Methylcyclohexanol B. 1-Methylcyclohexanone C. Formaldehyde and 1-methylcyclohexanone D. Acetaldehyde and acetone None 1 out of 30 Time is Up! Time's up
