Functional group interconversions, common reagents and catalysts for organic transformations - One Line Questions

1. What is the product of the reaction between an aldehyde and a Grignard reagent (RMgX) followed by acidic workup? — A secondary alcohol
2. What is the product of the reaction between a ketone and a Grignard reagent (RMgX) followed by acidic workup? — A tertiary alcohol
3. What is the product of the reaction between an ester and LiAlH4 followed by aqueous workup? — A primary alcohol
4. What is the product of the reaction between an ester and a Grignard reagent (excess)? — A tertiary alcohol
5. Which reagent is used to convert an ester to a carboxylic acid and an alcohol? — Acid hydrolysis (e.g., H2SO4/H2O)
6. The Wittig reaction is used to synthesize alkenes from carbonyl compounds. What are the key reactants involved? — Aldehyde/ketone and a phosphonium ylide
7. Which reagent is used for the conversion of a phenol to an ether? — Alkyl halide in the presence of a base (Williamson ether synthesis)
8. Which catalyst is commonly used in the Friedel-Crafts alkylation reaction? — Aluminum chloride (AlCl3)
9. The Oppenauer oxidation is a selective oxidation of secondary alcohols to ketones. What is the oxidizing agent typically used? — Aluminum isopropoxide in the presence of acetone
10. What is the product of the reaction between an alcohol and sodium metal (Na)? — An alkoxide and hydrogen gas
11. What is the product of the reaction between an aldehyde and HCN followed by hydrolysis? — An alpha-hydroxy carboxylic acid (cyanohydrin)
12. The Hell-Volhard-Zelinsky (HVZ) reaction involves the alpha-halogenation of carboxylic acids. What is the typical reagent used? — Br2/PBr3
13. What is the primary role of a reducing agent like DIBAL-H (Diisobutylaluminium hydride) at low temperatures? — Partial reduction of esters to aldehydes
14. What is the role of Lindlar's catalyst in the reduction of alkynes? — Partial reduction to cis-alkenes
15. Which reagent is commonly used to convert a primary alcohol to a secondary alkyl halide through a SN1 mechanism, if applicable? — Concentrated HBr or HCl
16. Fischer esterification is a reaction that converts a carboxylic acid and an alcohol into an ester. What is the typical catalyst used in this reaction? — Concentrated sulfuric acid (H2SO4)
17. The Sandmeyer reaction is used to replace a diazonium group with various substituents. What are the typical reagents used in this reaction? — CuX (where X = Cl, Br, CN)
18. Which reagent is used for the ozonolysis of alkenes to cleave the carbon-carbon double bond and form carbonyl compounds? — O3 followed by a reductive workup (e.g., Zn/H2O)
19. The conversion of an alkene to an alkane is typically achieved using which reagent combination? — H2/Pd
20. Which reagent is used to convert a terminal alkyne into a terminal alkene (cis-alkene)? — H2/Lindlar's catalyst
21. Which reagent is used for the conversion of an alkene to an alkane with anti-Markovnikov addition of HBr? — HBr in the presence of peroxides
22. The conversion of an alkene to an alkyl halide is an electrophilic addition reaction. What is the general reagent used? — HX (where X is a halogen)
23. The Wolff-Kishner reduction is used to convert carbonyl groups to methylene groups. What are the key reagents? — Hydrazine (N2H4) and a strong base (e.g., KOH)
24. What is the function of sodium ethoxide (NaOEt) in the synthesis of ethyl acetate from ethanol and acetic acid? — It acts as a solvent.
25. Which of the following reagents can convert an amide to an amine? — LiAlH4
26. The conversion of an alkene to an epoxide is typically achieved using which reagent? — m-CPBA (meta-Chloroperoxybenzoic acid)
27. Which reagent is used to convert an alkyl halide to a tertiary alcohol via a two-step process involving Grignard formation and reaction with a ketone? — Magnesium metal (Mg) followed by a ketone and acid workup
28. Which reagent is commonly used for the conversion of a primary amine to a diazonium salt? — NaNO2/HCl
29. Which reagent is used to convert an alkene to a vicinal diol (glycol)? — Osmium tetroxide (OsO4) followed by a reducing agent
30. What is the primary function of sodium borohydride (NaBH4) in organic synthesis? — Reduction of aldehydes and ketones to alcohols
31. What is the primary role of PCC (Pyridinium chlorochromate) in organic chemistry? — Oxidation of primary alcohols to aldehydes
32. Which catalyst is essential for the Wurtz reaction, used to form carbon-carbon bonds? — Sodium metal (Na)
33. Which reagent is used to convert a primary alcohol to a bromide via SN2 reaction? — PBr3
34. Which reagent can be used to convert a primary alcohol to a carboxylic acid? — KMnO4 (Potassium permanganate) under acidic conditions
35. Which catalyst is used in the catalytic hydrogenation of nitroarenes to anilines? — Pd/C (Palladium on carbon)
36. The Baeyer-Villiger oxidation converts ketones into esters. What is the typical oxidizing agent? — Peroxy acids (e.g., m-CPBA)
37. Which catalyst is often used in the hydrogenation of alkynes to alkanes? — Platinum (Pt)
38. Which reaction is used to convert an alkyl halide into a nitrile? — Reaction with sodium cyanide (NaCN)
39. What is the primary use of dicyclohexylcarbodiimide (DCC) in organic synthesis? — Formation of amide and ester bonds
40. What is the main purpose of using lithium aluminum hydride (LiAlH4) in organic synthesis? — All of the above
41. Which reagent is used for the conversion of an alkyne to a trans-alkene? — Sodium (Na) in liquid ammonia (NH3)
42. Which reagent is used to convert a carboxylic acid to a primary amine with one less carbon atom (via Curtius rearrangement)? — Sodium azide (NaN3) and heat
43. The conversion of an alkyl halide to an alkene is known as dehydrohalogenation. Which strong base is commonly used for this transformation? — Potassium tert-butoxide (KOtBu)
44. Which reagent is commonly used for the conversion of a carboxylic acid to an acid chloride? — Thionyl chloride (SOCl2)
45. What is the purpose of using a Lewis acid catalyst like AlCl3 in the Friedel-Crafts acylation reaction? — To activate the acyl halide and generate an electrophile
46. What is the purpose of using a dehydrating agent like P2O5 or concentrated H2SO4? — To remove water from a molecule
47. What is the purpose of using a protecting group for alcohols in multi-step synthesis? — To prevent the alcohol from reacting during other transformations
48. What is the role of osmium tetroxide (OsO4) in the Upjohn dihydroxylation? — To add two hydroxyl groups across a double bond syn-addition
49. What is the purpose of using copper(I) cyanide (CuCN) in the Rosenmund-von Braun reaction? — To replace a diazonium group with a nitrile group
50. What is the function of Raney Nickel in hydrogenation reactions? — To catalyze the addition of hydrogen to unsaturated compounds
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