Question

Describe a synthetic route for the following transformation: Br Br HCECH - CHCH2-¢-¢-CH2CH3 Br Br Provide the reagents, and when appropriate, the conditions you would use. Designate the order of the reactions by numbering each set of reagents.

Answer 1

Synthetic route:

Alkyne's hydrogens are acid. By using this chemistry we can alkate the alkyne.

1) After acidic hydrogen abstraction alkyne become hard nucleophilic which will attack the alkyl halide and gives allkylated product.

2) Acetelene have two acidic hydrogen so double time alkylation happens.

3) two equivalent of bromine add to the alkyne gives tetrabrominated target molecule.

H = 2 – I) Nah. s > Haº HOP -> H 3-1 1) Nah V. 2) ~B 13 ✓ Br Br-Br i Br • 4-1-1, Į CH₃ CH₂ -U- e-ch CH₂ / Br