Carbon-Carbon Bonds

Question 1

Alkylation of Terminal Alkyne
NaNH2/, R-X (X: LG)

Answer 1

• Triple bond must be in the primary position (terminal)
• Primary alkyl halides in the presence of a strong base like sodium amide

Question 2

Carbenoids (DuPont Process)
Zn(Cu), CH2I2

Answer 2

• Performed in a non-coordinating solvent like dichloromethane (DCM) or diethyl ether (DCE) at room temperature

Question 3

Diels-Alder Reaction
Diene + Dienophile

Answer 3

• A chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile

Question 4

Friedel-Craft Alkylation and Acylation
CCl3 (Benzene and R-Cl)

Answer 4

• Alkylation: attachment of a carbon chain to a benzene ring
• Acylation: attachment of a ketone to a benzene ring

Question 5

Addition of alkenes to other alkenes (e.g., polymerization)
NaOH

Answer 5

-Initiation with a SA

Question 6

Organometallic addition to carbonyl compounds (Grignard or R-Li reactions)
1) R-Li 2) H2O or
1) R- MgCl 2) H2O

Answer 6

• Same mechanism for Grignard reagents

Note: You should know how to make the R-MgCl and R-Li

R - X - (Mg/Ether) - R - MgX