ORGO exam 2 alekes and alkynes

Markovnikov

H+ added to the less substituted carbon

Anti-markovnikov

H+ added to more substituted carbon

Acid catalyzed hydration of alkene to make alcohol

Easy way to make alcohols, rearrangement is common though

Oxymercuation - demercuration reagents

1. Hg(OAc)₂, H₂O

2. NaBH₄, NaOH

Oxymercuation - demercuration overall scheme and rules

Alkene → alcohol

Markovnikov

Anti-addition

Free radical hydrobromination reagents

1. HBr

2. H2O2

Free radical hydrobromination scheme, rules

Alkene → primary alykyl halide

Follows Anti-markovnikov

Hydroboration-oxidation reagents

1. BH3 * THF

2. H2O2, NaOH

Hydroboration-oxidation scheme and rules

makes alcohol

Anti-markovnikov

Syn-addition

Catalytic hydrogenation - reduction reagents

1. H₂

2. Pt, Pd

Catalytic hydrogenation - reduction rule

Syn- addition

Syn dihydroxylation reagents

either : 1. OsO4, 2. H2O2

OR: 1. KMnO4, -OH, cold dilute

Syn dihyroxilation makes a

diol (two OH)

Cyclopropanation reaction

Cyclohexene with a carbonyl → cyclohexane with trangle where alkene was with same carbonyl

Cyclopropanation reagents

1. CH₂I₂

2. Zn, CuCl

Syn-addition

Epoxidation, alkene to epoxide, reagents, scheme

mcpBA

syn-addition

Addition of halogen to alkene, halogenation

Br₂ (or Cl₂)_, and CCl₄

Anti addition

Halohydrin formation

alkene + Br₂ and H2O

Anti-addition

Markovnikov OH

Ozonalysis

1. O3, -78C

2. (CH₃)₂S

Makes Ketone/aldehyde

Vicinal dihalide + KOH (molten) makes

internal alkyne

Vicinal dihalide + 1. NaNH₂,150C, 2. H2O makes

Terminal alkyne

Terminal alkyne + NaNH2

deprotonatesm makes acetylide anion

Reduction of alkyne to alkane reagents

2H₂, Pd

Reduction of alkyne to a cis-alkene reagents

Lindlars catalyst (Pd/BaSO4), H₂

Reduction of alkyne to a trans-alkene reagents

Na, NH₃(l) known as “dissolving metal reduction”

Addition of halogens to alkyne, reagents, note

2X_2, Cl₂, Or Br₂ makes tetrahalide

Addition of hydrogen halides to alkynes (HCl, HBr, HI) reagents, product, rule

2HX, makes geminal dihalide (halogen on same carbon)

markovnikov

Mercuric ion-catalyzed hydration of alkyne makes

ketone

Mercuric ion-catalyzed hydration of alkyne reagents

1. HgSO₄

2. H₂O, H₂SO₄

Hydroboration -oxidation of alkyne makes

aldehyde

Hydroboration -oxidation of alkyne reagents

1. Sia₂BH

2. H₂O_2, -OH

acid catalyzed ketoenol tautomerization

happens in Mercuric ion-catalyzed hydration of alkyne

follows protonation (acid) then deprotonation (by water)