CHEM 232- Reagent Cabinet List Questions With Complete
Solutions
NaNH2
Strong base good nucleophile
NaNH2
Turn an alkyne in good Nu
Friedel-Crafts Acylation
Ketone on benzene with acyl chloride
Hydroboration-Oxidation
H2O2 NaOH; Anti-Markovnikov, concerted SYN-Addition;
Adds OH to alkene
Hydration of Alkenes
Adds C=O bond at END or least substituted; Anti markovnikov
Bromination
Heat; Alkane to alkyl halide
Halogenation
1 equiv: alkyne->alkene or alkene -> alkane; Anti Addition; 2
equiv: alkyne to alkane
Halohydrin Synthesis
Leads to epoxidation with HOH or ROH; AntiAddition; X on
least substituted (regiospecific)
, Grignard Reagents
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
ClMs and ClTs; No inversion
Jones Reagent
CrO3, H2SO4, H2O; Primary alcohol to carboxylic acid;
Secondary alcohol to ketone
PCC
HCl and Pyridine; Primary alcohol to aldehyde; Secondary
alcohol to ketone
Benzene halogenation
FeBr3 and FeCl3
Hydrogenation
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
With OsO4 Stoichiometric
Dehydration
With Heat
Hydration
Solutions
NaNH2
Strong base good nucleophile
NaNH2
Turn an alkyne in good Nu
Friedel-Crafts Acylation
Ketone on benzene with acyl chloride
Hydroboration-Oxidation
H2O2 NaOH; Anti-Markovnikov, concerted SYN-Addition;
Adds OH to alkene
Hydration of Alkenes
Adds C=O bond at END or least substituted; Anti markovnikov
Bromination
Heat; Alkane to alkyl halide
Halogenation
1 equiv: alkyne->alkene or alkene -> alkane; Anti Addition; 2
equiv: alkyne to alkane
Halohydrin Synthesis
Leads to epoxidation with HOH or ROH; AntiAddition; X on
least substituted (regiospecific)
, Grignard Reagents
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
ClMs and ClTs; No inversion
Jones Reagent
CrO3, H2SO4, H2O; Primary alcohol to carboxylic acid;
Secondary alcohol to ketone
PCC
HCl and Pyridine; Primary alcohol to aldehyde; Secondary
alcohol to ketone
Benzene halogenation
FeBr3 and FeCl3
Hydrogenation
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
With OsO4 Stoichiometric
Dehydration
With Heat
Hydration