Question

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(b) 3-Phenylpentene reacts with acidified water to yield two compounds, H and I The formation of compound H follows Markovnikov's rules whereas carbocation rearrangement forms compound J -Fenilpentena bertindak balas dengan air berasid untuk menghasilkan du ebatian, H dan J.Pembentukan sebatian H mematuhi aturan Markovnikov sedangkan penyusunan semula karbokation membentuk sebatian J ) Draw the structural formulae for compounds H and J ukis formula struktur bagi sebatian H dan 2 marks 2 markah) Suggest the product formed when compound H is oxidised. Cadangkan hasil yang terbentuk apabila sebatian H dioksidakan (ii) II mark] II markah Gii) What will happen when compound J is oxidised with acidified KMno, solution? Explain your answer Apakah yang akan terjadi apabila sebatian 3 dioksidakan dengan arutan KMnO, berasid? Jelaskan jawapan anda 12 marks 12 markah

Answer 1

Formation of product H , which is a markonikov product:

Three steps are required for its formation,

CH 2. CH2-H CH Slovo HCE t, 0 CH CW CK 3 Secondo Carbo ctn CH HC@ H foxt H. in CM CM CH CM CM Ch2 Mankenikev Produet (H)

For the formation of product J the secondary carbocation formed in step 1 of formation of markonikov product is rearranged to give a more stable tertiary carbocation and further steps are similar to give the product J:

H-C-H 2Hshift CH CH 내 Carbo cabtn CH 2. Tert Carbe caston CH CH CH CH CH CK 3 0 CH CH Reaaded Pr out(J

(i) structural formula of H(2-Hydroxy-3-phenylpentane)

H-C-oH ーCH Pso dut (

Structure of J(3-Hydroxy-3-phenylpentane)

CK 3 CM 2 to Le CM2 CW 3

(ii) product formed when H is oxidised to form 3- Phenylpentan-2-one

(iii) oxidation of J using acidified KMnO₄ gives ethanoic acid and propiophenone.

J is a tertiary alcohol, it first undergo dehydration to form alkene , this alkene formed undergo oxidation and forms ketone and an acid .(J cannot undergo oxidation in presence of mild oxidising agent , can only oxidise in presence of acidified KMnO₄ by the process explained above).

C*3 cu2 acid fied CH KMnou CH3 CH 20 cw CH3