ORGO 2 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

Acid catalyzed hydration reagents

H2SO4, H20 (ROH form ether)

Acid catalyzed hydration H2SO4, H2O rules

Markovnikov alcohol, H-shift, C+,

Oxymercuation - demercuration reagents

1. Hg(OAc)₂, H₂O

2. NaBH₄, NaOH

Oxymercuation - demercuration of alkene overall scheme and rules

1. Hg(OAc)₂, H₂O

2. NaBH₄, NaOH

Alkene → alcohol

Markovnikov

Anti-addition
NO REARANGEMENT

Free radical hydrobromination reagents

1. HBr

2. H2O2

Free radical hydrobromination scheme, rules

Alkene → primary alykyl halide

Anti-markovnikov

Hydroboration-oxidation reagents

1. BH3 * THF

2. H2O2, NaOH

Hydroboration-oxidation scheme and rules

1. BH3 * THF

2. H2O2, NaOH

makes alcohol

Anti-markovnikov

Syn-addition

Catalytic hydrogenation - reduction reagents

1. H₂

2. Pt, Pd

Catalytic hydrogenation - reduction rule

1. H₂

2. Pt, Pd

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 reagents

Br₂ and H2O

halohydrin Br₂ and H2O

Anti addition, OH markovnikov

halohydrin Br₂ and ROH

forms ether

Ozonalysis

1. O3, -78C

2. (CH₃)₂S

Makes Ketone/aldehyde

Anti dihydroxilation reagents

mcPBA, H30+

Vicinal dihalide + KOH (molten) makes

internal alkyne

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

Terminal alkyne

Terminal alkyne + NaNH2

deprotonation 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, 2}Cl₂, Or 2Br₂ makes tetrahalide

Adds two halides to each carbon

Addition of 1 eq of Br2 or Cl2 to alkyne

Adds across the alkene

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

makes geminal dihalide (halogen on same carbon)

markovnikov

Mercuric ion-catalyzed hydration of alkyne makes

(1. HgSO4. 2. H2O, H2SO4)

ketone (MARKOVNIKOV)

Mercuric ion-catalyzed hydration of alkyne reagents

1. HgSO₄

2. H₂O, H₂SO₄

Hydroboration -oxidation of alkyne makes

(1. Sia2BH, 2. H2O2, OH)

aldehyde (ANTI-MARKOVNIKOV)

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)

Alkyne formation

NaNH2 attacks double br alkane