DAT alkyne reactions

markovnikov hydrohalogenation

markovnikov hydrohalogenation reactants and reagents

reactants:

• alkyne

reagents:

• HX( HI, HBr, HCl)

markovnikov hydrohalogenation products

1 halogen group is added to the most substituted alkyne position per reagent equivalent

anti-markovnikov hydrohalogenation

anti-markovnikov hydrohalogenation reactants and reagents

reactants:

• alkyne

reagents:

• HX( HI, HBr, HCl)

• ROOR

anti-markovnikov hydrohalogenation products

1 halogen group is added to the less substituted alkyne position per reagent equivalent

hydrohalogenation of internal alkynes

hydrohalogenation of internal alkynes product

an not regioselective halide addition to the alkyne, meaning unsymmetrical alkynes will generate a mixture of products while a symmetrical alkyne will only have one product(because an addition to either carbon results in the same molecule)

dihalogenation of alkynes

dihalogenation of alkyne reactants and reagents

reactants:

• alkyne

reagents:

• excess X₂( Br₂, Cl₂)

dihalogenation of alkynes products

two halogen atoms are added to each alkyne carbon, giving a total of four halogen atoms

catalytic hydrogenation

catalytic hydrogenation reactants and reagents

reactants:

• alkyne

reagents:

• H₂

• a metal catalysts(Pd, Pd/C,Pt)

catalytic hydrogenation products

alkane

lindlar’s catalyst hydrogenation

lindlar’s catalyst hydrogenation reactants and reagents

reactants:

• alkyne

reagents:

• lindlar’s catalyst

lindlar’s catalyst hydrogenation products

cis/Z alkene

dissolving metal reduction

dissolving metal reduction reactants and reagents

reactants:

• alkyne

reagents:

• Li/Na

• NH₃

dissolving metal reduction products

trans/E alkene

types of alkene reductions

1. catalytic hydrogenation

2. lindlar’s catalyst

3. dissolving metal reduction

acid catalyzed hydration of alkynes

acid catalyzed hydration of alkynes reactants and reagents

reactants

• alkyne

reagent;

• HgSO₄

• H₂SO₄, H₂O

acid catalyzed hydration of alkynes products

an enol intermediate that tautomerizes to a ketone at the markovnikov carbon

hydroboration oxidation of alkynes

hydroboration oxidation of alkynes reactants and reagents

reactants:

• alkyne

reagents:

• 1. R₂BH, THF

• 2. H₂O₂, NaOH

hydroboration oxidation of alkynes products

an enol intermediate that tautomerizes to an aldehyde at the anti- markovnikov carbon

ozonolysis of alkynes

ozonolysis of alkynes reactants and reagents

reactants:

• alkyne

reagents:

• 1. O₃

• 2. H₂O

ozonolysis of internal alkynes product

2 carboxylic acids

ozonolysis of terminal alkynes product

carboxylic acid and CO₂

alkylation of alkynes

alkylation of alkynes reactants and reagents

reactants:

• alkyne

reagents:

• NaNH₂

• Me or primary alkyl halide

alkylation of alkyne products

adds carbon atoms to the alkyne(remains an alkyne)