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Organic Chemistry Reactions
Ch 13-16 Alkynes, Delocalized pi-orbitals, benzene and aromaticity, and Elec. Attack on Benzene Derivatives
18
Organic Chemistry
Undergraduate 2
03/03/2010

Additional Organic Chemistry Flashcards

 


 

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Term

Hydrogenation of Benzene

 

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Definition
C6H6 + H2,catalyst→ C6H12
Term

Electrophilic Aromatic Substitution

Chlorination and Bromination

Definition

C6H6 + X2,FeX2 → C6H5X + HX

 

X = Cl, Br

 

FeX2 is a catalyst

Term

Electrophilic Aromatic Substitution

Nitration

Definition
C6H6 + HNO3, H2SO4 → C6H5NO3 + H2O
Term

Electrophilic Substitution

Sulfonation

Definition

C6H6 + SO3, H2SO4 → C6H5SO3H

 

(reversible)

Term

Friedel-Crafts Alkylation

 

Definition

C6H6 + RX + AlCl3 → C6H5R + HX

 

(R+ is subject to carbocation rearrangement)

Term

Friedel-Crafts Alkylation

 Intermolecular

Definition

C6H5-(CH2)4-Cl + AlCl3 → C6H4-C4H8 + HCl

 

C6H4-C4H8 = benzene ring attached by

a whole side to a cyclohexane ring

Term

Friedel-Crafts Alkylation

Alcohol Substrate

Definition
C6H6 + RC(OH)HR' + BF3, 60°C → C6H5-C(R)HCH3 +H2O
Term

Friedel-Crafts Alkanoylation

Alkanoyl Halides

Definition
C6H6 + RC(O)Cl + 1.AlCl3 2.H2O → C6H5-C(O)R + HCl
Term

Friedel-Crafts Alkanoylation

Anhydrides

Definition
C6H6 + CH3C(O)OC(O)CH3 + 1.AlCl3 2.H2O → C6H5-C(O)CH3 + CH3COOH
Term
Radical Allylic Halogenations
Definition
RCH2CH=CH2 + NBS,CCl4,hv → RC(Br)HCH=CH2 + RCH=CHCH2Br
Term
Sn2 Reactivity of Allylic Halides
Definition
CH2=CHCH2X + Nu:- + acetone (CH3)2C=O → CH2=CHCH2Nu + X-
Term
Allylic Grignard Reagents
Definition
CH2=CHCH2BR + Mg, ether → CH2=CHCH2MgBr
Term
Allyllithium Reagents
Definition
RCH2CH=CH2 + tMEDA → RC:-HCH=CH2 Li+
Term
Alkylation of Alkynyl Anions
Definition

RCΞCH + 1.NaNH2, liquid NH3 2.R'X → RCΞCR'

 

Sn2 reaction, R' must be a primary alkane

Term
Alkylation with Oxacyclopropane
Definition

RCΞCH +

1.RLi, THF 2.cyclo (CH2)2O 3.H+, H2O

RCΞCCH2CH2OH

 

attack takes place at the less substituted on unsymmetrical oxacyclopropanes

Term
Alkylation with Carbonyl Compounds
Definition

RCΞCH +

1.RLi, THF 2.R'(C=O)R" 3.H+, H2O

RCΞCC(OH)(R)(R')

Term
Reduction of an Alkyne to get a trans-Alkene
Definition

RCΞCR + 1.2Na, liquid NH3 2.H+,H2O → HRC=CHR

 

radical 4 step mechanism

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