CHEM 232- Reagent Cabinet List Test Questions and Answers Fully Solved Latest Update
2025-2026
Tollens Reagent - Answers NH4 aldehydes to carboxylic acids
Friedel-Crafts Alkylation - Answers Adds R group to Benzene; Beware rearrangements on
carbocation
Friedel-Crafts Acylation - Answers Ketone on benzene with acyl chloride
Hydroboration-Oxidation - Answers H2O2 NaOH; Anti-Markovnikov, concerted SYN-Addition;
Adds OH to alkene
Hydration of Alkenes - Answers Adds C=O bond at END or least substituted; Anti markovnikov
Bromination - Answers Heat; Alkane to alkyl halide
Halogenation - Answers 1 equiv: alkyne->alkene or alkene -> alkane; Anti Addition; 2 equiv:
alkyne to alkane
Halohydrin Synthesis - Answers Leads to epoxidation with HOH or ROH; AntiAddition; X on least
substituted (regiospecific)
Grignard Reagents - Answers C(-) Nucleophile; Only react with Carbonyls and epoxides (Sn2);
STRONG BASE; C=O to C-OH; 1-2 carbonyl addition
Activation of Alcohols via Sulfonyl Chlorides - Answers ClMs and ClTs; No inversion
Jones Reagent - Answers CrO3, H2SO4, H2O; Primary alcohol to carboxylic acid; Secondary
alcohol to ketone
PCC - Answers HCl and Pyridine; Primary alcohol to aldehyde; Secondary alcohol to ketone
Benzene halogenation - Answers FeBr3 and FeCl3
Hydrogenation - Answers Alkenes/Alkynes to Pt0; SYN; Alkenes-Pt0, pb(OAc)2, quinoline; Cis
Alkene; Of Benzene Ring: Ni, Heat, high pressure H2; Benzylic Position: H2 Pd/C
Syn-Dihydroxylation - Answers With OsO4 Stoichiometric
Dehydration - Answers With Heat
Hydration - Answers With H2O; Markovnikov
Alkene Isomerization - Answers To form most stable alkene
HydroHalogenation - Answers HBr and HCl; Marvonikov's Rule; 1 equi for alkyne to alkene;
, Excess for alkyne to alkane (2nd rxn slow); Beware carbocation
Clemmensen reduction - Answers Requires Heat
Oxymercuration Reduction - Answers Hg(OAc)2; Alkene
HOH or HOR (Anti) - Answers 2.NaBH4, NaOH (Marvovnikov)
HgSO4 - Answers Hydration of Alkene with Catalytic Hg
Enol during tautomerization - Answers H2SO4, H20
HI - Answers Breaks ethers
HNO3 - Answers Nitration of Benzene with HNO3 and H2SO4
HOR - Answers Ethers
Weak base poor nucleophile - Answers HOR
HSR - Answers Weak base good nucleophile
KOC(CH3)3 (Potassium t-butoxide) - Answers E2 Reactions
Li - Answers 2 equi to make organolithium
LiAlH4 - Answers H+ nucleophile
LiAlH4 - Answers o=C to OH-C
LiAlH4 - Answers Opens epoxides
LiAlH4 - Answers Deprotonates alcohols
LiAlH4 - Answers SN2 with halogens and Sulfonate ester
LiAlH4 - Answers Reduces esters and carboxylic acids to primary OH
LiAlH4 - Answers 1-2 carbonyl addition
LiCu(R)2 (Gilman reagents, organocuprate) - Answers Carbonyls and epoxides
Gilman - Answers results in 1-4 addition
Light - Answers Can be used in place of heat
LiN(CH(CH3)2)2 (LDA, Lithium diisopropylamide) - Answers Strong base
LiR - Answers The Li should be listed first for an organolithium reagent.
2025-2026
Tollens Reagent - Answers NH4 aldehydes to carboxylic acids
Friedel-Crafts Alkylation - Answers Adds R group to Benzene; Beware rearrangements on
carbocation
Friedel-Crafts Acylation - Answers Ketone on benzene with acyl chloride
Hydroboration-Oxidation - Answers H2O2 NaOH; Anti-Markovnikov, concerted SYN-Addition;
Adds OH to alkene
Hydration of Alkenes - Answers Adds C=O bond at END or least substituted; Anti markovnikov
Bromination - Answers Heat; Alkane to alkyl halide
Halogenation - Answers 1 equiv: alkyne->alkene or alkene -> alkane; Anti Addition; 2 equiv:
alkyne to alkane
Halohydrin Synthesis - Answers Leads to epoxidation with HOH or ROH; AntiAddition; X on least
substituted (regiospecific)
Grignard Reagents - Answers C(-) Nucleophile; Only react with Carbonyls and epoxides (Sn2);
STRONG BASE; C=O to C-OH; 1-2 carbonyl addition
Activation of Alcohols via Sulfonyl Chlorides - Answers ClMs and ClTs; No inversion
Jones Reagent - Answers CrO3, H2SO4, H2O; Primary alcohol to carboxylic acid; Secondary
alcohol to ketone
PCC - Answers HCl and Pyridine; Primary alcohol to aldehyde; Secondary alcohol to ketone
Benzene halogenation - Answers FeBr3 and FeCl3
Hydrogenation - Answers Alkenes/Alkynes to Pt0; SYN; Alkenes-Pt0, pb(OAc)2, quinoline; Cis
Alkene; Of Benzene Ring: Ni, Heat, high pressure H2; Benzylic Position: H2 Pd/C
Syn-Dihydroxylation - Answers With OsO4 Stoichiometric
Dehydration - Answers With Heat
Hydration - Answers With H2O; Markovnikov
Alkene Isomerization - Answers To form most stable alkene
HydroHalogenation - Answers HBr and HCl; Marvonikov's Rule; 1 equi for alkyne to alkene;
, Excess for alkyne to alkane (2nd rxn slow); Beware carbocation
Clemmensen reduction - Answers Requires Heat
Oxymercuration Reduction - Answers Hg(OAc)2; Alkene
HOH or HOR (Anti) - Answers 2.NaBH4, NaOH (Marvovnikov)
HgSO4 - Answers Hydration of Alkene with Catalytic Hg
Enol during tautomerization - Answers H2SO4, H20
HI - Answers Breaks ethers
HNO3 - Answers Nitration of Benzene with HNO3 and H2SO4
HOR - Answers Ethers
Weak base poor nucleophile - Answers HOR
HSR - Answers Weak base good nucleophile
KOC(CH3)3 (Potassium t-butoxide) - Answers E2 Reactions
Li - Answers 2 equi to make organolithium
LiAlH4 - Answers H+ nucleophile
LiAlH4 - Answers o=C to OH-C
LiAlH4 - Answers Opens epoxides
LiAlH4 - Answers Deprotonates alcohols
LiAlH4 - Answers SN2 with halogens and Sulfonate ester
LiAlH4 - Answers Reduces esters and carboxylic acids to primary OH
LiAlH4 - Answers 1-2 carbonyl addition
LiCu(R)2 (Gilman reagents, organocuprate) - Answers Carbonyls and epoxides
Gilman - Answers results in 1-4 addition
Light - Answers Can be used in place of heat
LiN(CH(CH3)2)2 (LDA, Lithium diisopropylamide) - Answers Strong base
LiR - Answers The Li should be listed first for an organolithium reagent.
