Questions with Actual Detailed Answers
2026 Updated.
Radical Halogenation of Alkanes
(X2, hv) - Answer alkane → racemic alkyl halide
SN1
(weak nuc) - Answer 2° or 3° alkyl halide → racemic alcohol
SN2
(strong nuc, polar aprotic solv) - Answer 1° or 2° alkyl halide → umbrella-flipped substituted
alkane
E1
(weak nuc/base, Δ) - Answer 2° or 3° alkyl halide → alkene
E2
(strong base, polar aprotic solv) - Answer any alkyl halide → alkene
Ester Hydrolysis
(1. strong nuc
2. strong base) - Answer 1° or 2° alkyl halide → alcohol
Reductions [R] of Carbonyls
(1. [R] agent
2. SA) - Answer carbonyl → alcohol
Jones/Chromic Acid Oxidation [O]
(CrO3, H2SO4, H2O) - Answer methanol, 1° or 2° alcohol → carbonyl
Aldehyde Synthesis w/ PCC/PDC [O]
(DCM) - Answer 1° or 2° alcohol → aldehyde
Organometallic ABC
, (1. THF
2. H2O, HCl) - Answer organometallic → protonated non-metallic hydrocarbon
Organometallic E2
(toluene) - Answer 2° alkyl halide → alkene
Organometallic Additions to Carbonyls
(1. THF
2. H2O, HCl) - Answer carbonyl → trisubstituted alcohol
Alkoxide Synthesis
(strong base) - Answer alcohol → alkoxide (a strong nuc!)
Alkyloxonium Synthesis
(SA, H2O) - Answer alcohol → alkyloxonium (a good LG)
Alkyl Halide Syntheses
(multiple options) - Answer alcohol → alkyl halide
Williamson Ether Synthesis
(DMSO) - Answer alkoxide + 1° alkyl halide → ether
Intramolecular Ether Synthesis
([R] agent, THF) - Answer halohydrin → epoxide/episulfide
Acidic Ether Synthesis
(SA, H2O) - Answer 2 alcohols → ether
Ether Cleavage
(SA, H2O) - Answer ether → alcohol + byprodt
Organometallic Additions w/ Protecting Groups - Answer N/A
Epoxides in Basic Conditions
(1. weak