Ochem reactions

Halogenation of Alkenes - Addition of X₂

-reagents: Br2, Cl2

-regiochemistry: not relevant

-stereochemistry: anti

Halohydrins from Alkenes - Addition of HOX

-reagents: X2 with H2O or NBS (gives Br and OH as products)

-regiochemistry: not relevant

-stereochemistry: anti

Hydration of Alkenes - Addition of H₂O by Oxymercuration

-reagents: 1. HG(OAc)2, H2O 2. NaBH4

-regiochemistry: Markovnikov

-stereochemistry: not relevant (sometimes goes to the back)

Hydration of Alkenes - Addition of H₂O by Hydroboration

-reagents: BH3, THF (gives BH2 substituent) or BH3, THF, H2O2, NaOH, and H2O (gives OH sub)

-regiochemistry: Anti-Markovnikov

-stereochemistry: not relevent

Reduction of Alkenes - Hydrogenation

-reagents: H2 and Pt

-regiochemistry: not relevant

-stereochemistry: syn

Oxidation of Alkenes - Epoxidation

-reagents: MCPBA, (CH3)2CO or MMPP, CHCL3 (gives epoxide, always comes towards the screen) or MCPBA H2O, and H3O or OH (gives diol)

-regiochemistry: not relevant

-stereochemistry: anti (for diol)

Oxidation of Alkenes - Hydroxylation

-reagents: OsO4 and H2S, or OsO4, NaHSO4, and H2O

-regiochemistry: not relevant

-stereochemistry: syn

-produces two OH bonds

Oxidation of Alkenes - Cleavage to Carbonyl Compounds

-reagents: O3 with reductive workup like Zn/H3O or KMnO4 with heat (acid) (makes CO2 if pi bond is terminal)

-regiochemistry: N/A

-stereochemistry: N/A

Addition of Carbenes to Alkenes - Cyclopropane Synthesis

-reagents: CH2 (carbene), hv with Zn, Cl or CCl2 (carbenoid)

-regiochemistry: N/A

-stereochemistry: cis- both wedged or hashed, trans- one hash, one dash

Preparation of Alkynes - Elimination Reactions of Dihalides

-reagents: NaNh2, NH3, H2O (bases), might need extra if terminal

-regiochemistry:

-stereochemistry:

Reactions of Alkynes - Addition of HX

-reagents: HX

-regiochemistry: Markovnikov

-stereochemistry: anti

Reactions of Alkynes - Addition of X2

-reagents: X2

-regiochemistry: Markovnikov

-stereochemistry: anti

Hydration of Alkynes

-reagents: listed on image

-regiochemistry: anti (Sia)

-stereochemistry: syn (Sia)

Reduction of Alkynes 1

-reagents: H2, Pd/C

-regiochemistry: N/A

-stereochemistry: turns into trans alkane

Reduction of Alkynes 2

-reagents: H2, Lindlar catalyst

-regiochemistry: N/A

-stereochemistry: turns into cis alkene

Reduction of Alkynes 3

-reagents: Na/NH3

-regiochemistry: N/A

-stereochemistry: turns into trans alkene

Oxidative Cleavage of Alkynes

-reagents: O3 with H2O or KMnO4/OH in H3O

-terminal alkyne will make CO2

-if there are no O’s in the reagents (besides O3 or KMnO4) then no OH group

Alkylation of Acetylide Anions

-reagents: NaNH2/NH3 and XC…….. or RRO with H3O

-needs alkyne and halide to work

-bonds to triple bond end

-can add in parts