Reagents List/ Cheat Sheet

Markovnikov's Rule

When HX adds to an alkene, the H attaches to the less substituted carbon, and the halide (X) attaches to the more substituted carbon.

Anti-Markovnikov Addition

When HBr adds to an alkene in the presence of peroxides (ROOR), the H attaches to the more substituted carbon, and the Br attaches to the less substituted carbon.

Hydration of Alkenes

Reaction of alkenes with H3O+ results in the addition of H on one carbon and an OH group on the more substituted carbon (following Markovnikov's rule).

Markovnikov Addition Mechanism

In the addition of HCl, HBr, or H3O+, a carbocation intermediate forms, which may rearrange.

Oxymercuration-Demercuration

The addition of water to alkenes using Hg(OAc)2, followed by NaBH4, results in an OH group on the more substituted carbon without rearrangement.

Hydroboration-Oxidation

The addition of BH3 followed by H2O2 and OH- results in an OH group attached to the less substituted carbon, with the addition occurring syn (H and OH on the same face).

Halogenation of Alkenes

The reaction of alkenes with X2 (Br2, Cl2) results in the addition of one X atom on each carbon, with an anti configuration.

Halohydrin Formation

When alkenes react with X2 in the presence of H2O, one X attaches to the less substituted carbon and OH attaches to the more substituted carbon in an anti configuration.

Catalytic Hydrogenation

The addition of H2 in the presence of metals (Pt/Pd/Ni) to alkenes results in syn addition, converting alkenes to alkanes.

Diol Formation

The reaction of alkenes with OsO4 followed by NaHSO3 results in the formation of a diol (two OH groups) with syn addition.

Ozonolysis of Alkenes

The reaction of alkenes with O3 followed by Zn or S(CH3)2 cleaves the double bond, forming carbonyl compounds.

Alkyne Catalytic Hydrogenation

The reaction of alkynes with H2 and metal catalysts converts alkynes to alkanes by adding 2 hydrogen atoms.

Lindlar Catalyst

Used to convert alkynes to cis alkenes through partial hydrogenation.

Trans Alkene Formation

The reaction of alkynes with sodium (Na) or lithium (Li) in liquid ammonia (NH3) produces trans alkenes.

Alkyne Addition of HX

The addition of 1 equivalent of HX to an alkyne results in H on one carbon and X on the more substituted carbon.

Double Addition of HX to Alkynes

The addition of excess HX to an alkyne results in both halogens attaching to the same carbon, converting the alkyne to an alkane.

Nucleophilic Acyl Substitution in Alkynes

The reaction of terminal alkynes with HgSO4 and H2O results in a ketone via Markovnikov addition.

Alkyne Transformation to Aldehyde

The hydroboration of terminal alkynes with 1) BH3-type reagents and 2) H2O2, OH- leads to the formation of an aldehyde.

Radical Halogenation

The reaction of alkanes with X2 in the presence of light (hv) results in radical halogenation, substituting hydrogen for a halogen.

Alkylation of Terminal Alkynes

The process of adding a carbon chain to a terminal alkyne using NaNH2 and an alkyl halide.

Alkyne Synthesis from Alkenes

The reaction of alkenes with X2 followed by a strong base like NaNH2 leads to the formation of alkynes through double elimination.