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Chapter 15: Q59. (page 570)

Question: Devise a synthesis of CH2 CH2CH2CH2Br from HC鈮�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鈥檚 rule

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Most popular questions from this chapter

Question: When HBr adds to (CH3)2C=CH2 under radical conditions, two radicals are possible products in the first step of chain propagation. Draw the structure of both radicals and indicate which one is formed. Then draw the preferred product from HBr addition under radical conditions.

Question: (a) Draw the products (including stereoisomers) formed when 2-methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4-dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.

Question: As described in Section 9.16, the leukotrienes, important components in the asthmatic response, are synthesized from arachidonic acid via the hydroperoxide 5-HPETE. Write a stepwise mechanism for the conversion of arachidonic acid to 5-HPETE with O2 .

Question: Identify the structure of a minor product formed from the radical chlorination of propane, which has molecular formula C3H6Cl2 and exhibits the given 1H NMR spectrum.

Question: The triphenylmethyl radical is an unusual persistent radical present in solution in equilibrium with its dimer. For 70 years the dimer was thought to be hexaphenylethane, but in 1970, NMR data showed it to be A.

a. Why is the triphenylmethyl radical more stable than most other radicals?

b. Use curved arrow notation to show how two triphenylmethyl radicals dimerize to form A.

c. Propose a reason for the formation of A rather than hexaphenylethane.d. How could 1 H and 13C NMR spectroscopy be used to distinguish between hexaphenylethane and A?
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