PHA615 LEC: Alkene Alkyne Aromatic Reactions Reagents

H2; Pd/PtO2

Reagent and catalyst for hydrogenation

H2O; BH3/THF and H2O2, NaOH

Reagent and catalyst for hydroboration

H2O; Hg(OAc)2 and NaBH4

Reagent and catalyst for oxymercuration-demercuration

ROH; H+

Reagent and catalyst for ether formation

HX; ether (H2O2 if NM)

Reagent and catalyst for hydrohalogenation

X2; DCH (CH2Cl2) or CCl4

Reagent and catalyst for halogenation

X2 in H2O

Reagent for halohydrin

mCPbA

Reagent for epoxidation

KMnO4; basic soln

Reagent and catalyst for hydroxylation

KMnO4; acid

Reagent and catalyst for bond cleavage

O3; Zn

Reagent and catalyst for ozonolysis

radical

Reagent for Polymerization

2H2; Pd/C

Reagent and catalyst for hydrogenation for alkyne (saturated)

H2; Lindlar’s

used for alkynes to produce cis-double bond

geminal halides

result of excess HX in alkyne

cis vicinal halide

result of excess X2 in alkyne

H2O; H2SO4 or HgSO4

Reagents for hydration for alkyne

M = ketone; Anti = aldehyde

result of tautomerization

NaNH2 and RX

reagents for acetylide formation

H2O; H3PO4

reagent and catalyst for hydration

fumarase

catalyst for enzymatic hydration

Br2; FeBr3

reagents and catalyst for aromatic halogenation (+Br)

Cl2; FeCl3

reagents and catalyst for aromatic halogenation (+Cl)

I2;H2O2 or CuCl2

reagents and catalyst for halogenation (+I)

CuF2; heat

reagents and catalyst for halogenation (+F)

HNO3; H2SO4

reagents and catalyst for nitration (NO2 first step)

SnCl2 or Fe, H3O+ or H2, Pd; H2SO4

reagents and catalyst for nitration (NH2 second step)

fuming sulfuric acid (SO3 and H2SO4)

reagents and catalyst for Sulfonation

RX; AlX3

reagents and catalyst for Friedel-Crafts Alkylation

RCOX; AlX3

reagents and catalyst for Friedel-Crafts Acylation

3 H2; Pt/Rh under high pressure

reagents and catalyst for Hydrogenation (aromatic)

Br; NBS, Ph(CO2)2 or CCl4

reagents and catalyst for Bromination of Alkyl Side Chain

KMnO4; H2O or H+

reagents and catalyst for Oxidation of Alkyl Side Chain

H2 or Pd

catalyst for Ketone and Nitro Reduction

Electrophilic Addition

type of reaction mechanism for alkenes

Electrophilic Addition

type of reaction mechanism for alkynes

Electrophilic Substitution

type of reaction mechanism for aromatics

electrophile

Product in aromatic

nucleophile

Product in alkene

toulene

aniline

phenol

xylene

cresol

styrene