Alkenes and Alkynes reactions & reagents

Hydrohalogenation ALKENES: Addition of H and X across double bond

reagents: HX

Anti Markovnikov Hydrohalogenation ALKENES: anti mark. addition of HBr across double bond

Reagents: HBr ONLY, ROOR

Acid Catalyzed hydration ALKENES: Addition of H20 across double bond

Reagents: non nucleophilic acids (H3O+, H+, HNO3, H2SO4) and H20

Variation of acid cat. hydration ALKENES: addition of H and R-O across double bond

Reagents: non nucleophilic acids (H3O+, H+, HNO3, H2SO4) and ROH

Oxymercuration Demercuration ALKENES: Addition of nuc-H across double bond without carbocation rearrangements

Reagents: 1.) Hg(OAc)2, nuc-H 2.)NaBH4

Hydroboration Oxidation ALKENES: anti mark. SYN addition of H20 across double bond

Reagents: 1.) BH3 * THF 2.) H2O2, NaOH

Hydrogenation ALKENES: SYN Addition of H2 across double bond

Reagents: H2 and metal catalyst (Pd/C, Ni, Pt)

Halogenation ALKENES: ANTI Addition of X2 across double bond

Reagents: X2 (Cl2, Br2, I2)

Halohydrin formation ALKENES: ANTI Addition of X and OH across double bond

Reagents: X2 (Cl2, Br2, I2) and H2O/Alcohol

Anti Dihydroxylation ALKENES: ANTI Addition of OH and OH across double bond

Reagents: mcPBA and H3O+

Syn Dihydroxylation ALKENES: SYN addition of OH and OH across double bond

Reagents: 1.) OSO4 2.)H2O2 OR 1.) KMnO4 2.) -OH, cold

Ozonolysis ALKENES: cleaves double bonds and creates two new C=O double bonds

Reagents: 1.) O3 2.) DMS

Variation of Ozonolysis ALKENES: Cleaves double bonds and creates two new C=O double bonds, and converts allylic H into OH

Reagents: 1.) O3 2.) H2O2

Making Internal Alkynes: Converting a halogenated alkane/halide into an INTERNAL alkyne

Reagents: xs KOH @ 200 C

Making External Alkynes: Converting a halogenated alkane/halide into an EXTERNAL alkyne

Reagents: 1.) 3eq NaNH2 @ 150 C 2.) H2O

Reduction of Alkyne to Alkane: Adds H2 across triple bond until NO PI BONDS LEFT

Reagents: H2 and Pd/C

Reduction of Alkyne to Cis Alkene: Adds H2 across triple bond to form a CIS ALKENE

Reagents: H2, Lindler's Catalyst

Reduction of Alkyne to Trans Alkene: Adds H2 across triple bond to form a TRANS ALKENE

Reagents: Na* and NH3 (l) @ -78 C

Hydrohalogenation ALKYNES: single or double addition of HX across triple bond

Reagents: HX (for single addition) or xs HX (for double addition)

Acid Catalyzed Hydration ALKYNES: addition of OH and H across triple bond to form a ketone product

Reagents: HgSO4 H2SO4 and H2O

Acid Catalyzed Tautomerization ALKYNES: last step of acid cat. hydration, converting the enol product to the ketone product

Reagents: H3O+

Hydroboration Oxidation ALKYNES: Addition of OH and H across triple bond to form an aldehyde product

Reagents: 1.) Sia2 BH 2.) H2O2, NaOH

Base Catalyzed Tautomerization ALKYNES: last step of hydroboration oxidation, converting the enol product to the aldehyde product

Reagents: -OH

Halogenation ALKYNES: single or double ANTI addition of X2 across triple bond

Reagents: X2 or xs X2 (Cl2, Br2)

Ozonolysis ALKYNES: cleaves triple bonds to create two new C=O double bonds with an adjacent OH (carboxylic acids)

Reagents: O3 and H2O

Alkylation of Terminal Alkynes: deprotonates terminal alkyne and adds R or RO onto the end

Reagents: 1.) NaNH2 2.) R-X (adds R, X is Br, Cl, or I) or RO-H (adds RO)