Q5(c)(ii). Products W, X, Y and Z from toluene
Identify the products W, X, Y and Z in the following reactions: toluene with NBS, hν, dibenzoyl peroxide (Bz₂O₂) gives W; CrO₃, Ac₂O, then H₃O⁺ gives X; Ac₂O, NaOAc, Δ gives Y; excess LiAlH₄ gives Z. [reaction scheme given in the paper]
Answer in brief
W = benzyl bromide; X = benzaldehyde; Y = (E)-cinnamic acid; Z = 3-phenylpropan-1-ol.
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The full model answer
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CoversNBS benzylic brominationCrO₃–Ac₂O oxidationPerkin reactioncinnamic acidLiAlH₄ reduction
All parts of Question 5
- 5(a) Nucleosides, nucleotides and the primary structure of DNA and RNA10 marks
- 5(b) Photolysis of 2-methylcyclohexanone in solution10 marks
- 5(c)(i) 1-Ethynylcyclopentanol from acetylene5 marks
- 5(c)(ii) Products W, X, Y and Z from toluene5 marks
- 5(d) N–H stretching of amines in IR; alcohols in PMR10 marks
- 5(e) Matching three sets of IR and NMR data with five structures10 marks