List of Some Important Organic Reactions and Reagents
Reaction Reagent(s) and Conditions
Hydration of C=C double bonds by
the Markovnikoff’s rule
Hydration of C=C double bonds by
the Markovnikoff’s rule
Hydration of C=C double bonds
against the Markovnikoff’s rule
Hydrobromination of C=C double
bonds by the Markovnikoff’s rule
Hydrobromination of C=C double
bonds against the Markovnikoff’s
rule
Dehydration of alkohols
Dehydrohalogenation of alkyl
halides
Hydrogenation of C=C double
bonds
Dehydrogenation of alkanes
Comments
H2O, H+ 1. May be complicated by
reactions of carbocations (e.g.
rearrangements)
2. Also works for addition of
alcohols
1. Hg(OAc)2, H2O 1. Carbocations are not involved
2. NaBH4 2. Also works for addition of
alcohols
1. BH3 –based reagent Occurs in the syn-fashion
2. H2O2/OH-
HBr/dark 1.Also works for addition of
HCl, HF and HI
2. Also works for alkynes
3. May be complicated by
reactions of carbocations
HBr/source of free radicals (e.g. 1. Doesn’t work for addition of
irradiation or peroxides) HCl, HF and HI
2. Also works for alkynes
3. May be complicated by
reactions of free radicals
H+, heat 1. May be complicated by
reactions of carbocations
2. May be complicated by
reactions of substitution
3. Goes by the Zaitsev’s rule
t-BuOK 1. Occurs by the Zaitsev’s rule
(The larger the leaving group,
the worse the rule works)
2. Occurs in the anti-fashion (if
conflicts with the Zaitsev’s rule,
overrides it)
3.Also works with weaker
bases, but may be complicated
by substitution
H2/catalyst (e.g. Pt) 1.Occurs in the syn-fashion
2. Also works for some C=O
double bonds
Catalyst (e.g. Pt)/heat 1. Occurs in the syn-fashion
2. Also works for some alcohols
3. May lead to stable cyclic
compounds instead of
compounds with C=C double
bonds
Bromination of alkenes (addition)
Bromination of alkenes
(substitution)
Dihydroxylation of C=C double
bonds
Dihydroxylation of C=C double
bonds
Epoxidation
Ozonolysis
Oxidation of alcohols to aldehydes
or ketons
Oxidation of alcohols to acids
Polymerization of alkenes
Substitution
Hydration of alkynes by the
Markovnikoff’s rule
Hydration of alkynes against the
Markovnikoff’s rule
Hydrogenation of alkynes
Hydrogenation of alkynes
Deprotonation
Compiled by Dr. Grigoriy Sereda.
Br2/dark 1. Occurs in the anti-fashion
2. Also works for chlorination
and iodination
3. Also works for alkynes
4. May be complicated by
carbocation – like reactions
5. May be affected by
participation of nucleophilic
solvents
NBS, peroxides 1. Occurs at the allyl position
2. Also works for chlorination
OsO4/H2O or KMnO4/OH-, H2O Leads to cis-diols
Peroxoacids, H2O Leads to trans-diols
Peroxoacids or O2/Ag, heat This is the first step of the
previous reaction
1. O3 1. Leads to aldehydes or ketons
2. (CH3)2S 2. Also works for aromatic
compounds
PCC 1. Tertiary alcohols don’t react
2. Tolerates the presence of
C=C double bonds
KMnO4/H+ or K2Cr2O7/H+ 1. For secondary and tertiary
alcohols cleaves C-C – bonds
2. May give a messy mixture if
a C=C double bond is present
Radicals or acids or bases The reaction product is messy,
but often practically useful
Depends on the starting material See lecture notes
Hg2+, H+, H2O Results in formation of ketones
(except acetylene)
1. BH3 –based reagent Results in formation of
2. H2O2/OH- aldehydes
H2, Lindlar’s catalyst Results in formation of
cis-alkenes
Na in liquid NH3 Results in formation of
trans-alkenes
NaNH2 or other very strong bases Works for 1-alkynes only
Jan 2003 Available at www.usd.edu/~gsereda