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Chapter 15: Q59. (page 570)

Question: Devise a synthesis of CH2 CH2CH2CH2Br from HC≡CH You may use any other required organic or inorganic reagents.

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Step by step solution

01

 Step 1: Reagents required for the synthesis

The synthesis reaction takes place in the presence of these reagents:

  • NaH: abstraction of an acidic proton
  • CH3CH2 Br: addition of alkyl group
  • Lindlar catalyst: reduction of alkyne to cis-alkene
  • HBr in the presence of peroxide: radical mechanism giving alkyl halide from an alkene
02

Stepwise mechanism

Step 1

Acidic hydrogen abstraction by NaH base

Step 2

Substitution of the alkyl group

Step 3

Reduction of alkyne

Step 4

Formation of alkyl halide following anti-Markovnikoff’s rule

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Most popular questions from this chapter

Question: PGF2α (Section 4.15) is synthesized in cells from arachidonic acid C20H32O2 using a cyclooxygenase enzyme that catalyzes a multistep radical pathway. Part of this process involves the conversion of radical A to PGG2, an unstable intermediate, which is then transformed to PGF2α and other prostaglandins. Draw a stepwise mechanism for the conversion of A to PGG2 . (Hint: The mechanism begins with radical addition to a carbon-carbon double bond to form a resonance-stabilized radical.

Question: When two monomers (X and Y) are polymerized together, a copolymer results. An alternating copolymer is formed when the two monomers X and Y alternate regularly in the polymer chain. Draw the structure of the alternating copolymer formed when the two monomers, CH2CCl2 and CH2,=CHC6H5 are polymerized together.

Question: (a)Draw the structure of polystyrene, the chapter-opening molecule, which is formed by polymerizing the monomer styrene, C6H5CH=CH2. (b) What monomer is used to form poly(vinyl acetate), a polymer used in paints and adhesives?

Question: Which C-H bond in each compound most readily broken during radical halogenation?

a.

b.

c.

Question: Draw the products of each reaction.

a.

b.

c.
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