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Study the reaction scheme below and answer the questions which follow. (i) Give the reagents and reaction conditions for the steps represented by i to iv. (ii) Give the structures of compounds A to D.

Chemistry

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6. (a) Study the reaction scheme below and answer the questions which follow.

(i) Give the reagents and reaction conditions for the steps represented by i to iv.

StepReagent(s)Reaction conditions
iAlcoholic KOHHeat (reflux)
iiHBrRoom temperature
iiiAqueous KOHHeat (reflux)
ivHClRoom temperature

(ii) Give the structures of compounds A to D.

Based on the reaction scheme:

  • Compound D is explicitly given as CH3_3(CH2_2)3_3OH (1-butanol).
  • Step iii is the conversion of A (C4_4H9_9Br) to D (1-butanol). This is a nucleophilic substitution where Br is replaced by OH. Therefore, A must be 1-bromobutane.
  • Step i is the conversion of A (1-bromobutane) to B (C4_4H8_8). This is an elimination reaction, forming an alkene. Thus, B is but-1-ene.
  • Step ii is the conversion of B (but-1-ene) to C (C4_4H9_9Br). This is the addition of HBr to an alkene. According to Markovnikov's rule, the major product is 2-bromobutane.

A: CH3CH2CH2CH2Br\boxed{\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Br}} (1-bromobutane)
B: CH3CH2CH=CH2\boxed{\text{CH}_3\text{CH}_2\text{CH}=\text{CH}_2} (But-1-ene)
C: CH3CH2CH(Br)CH3\boxed{\text{CH}_3\text{CH}_2\text{CH(Br)}\text{CH}_3} (2-bromobutane)
D: $\boxed{CH_3CH_2CH_2\text

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