Q6(c). Addition of HCl to an α,β-unsaturated acid
The reaction of propanoic acid with HCl can form two possible products, but only one is formed in major quantity. Write the structure of the two products and give suitable explanation.
Answer in brief
Reading the acid as propenoic (acrylic) acid: major product 3-chloropropanoic acid, ClCH₂CH₂COOH. The other possible product, 2-chloropropanoic acid, CH₃CHClCOOH, is minor or not formed.
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Coversacrylic acidconjugate addition1,4-addition of HClanti-Markovnikov3-chloropropanoic acid
All parts of Question 6
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- 6(b) Bromine addition: styrene reacts faster than propene4 marks
- 6(c) Addition of HCl to an α,β-unsaturated acid4 marks
- 6(d) Michael addition of a cyclic 1,3-dione to cyclohex-2-enone4 marks
- 6(e) Hydroboration–oxidation of 1-methylcyclohexene4 marks
- 6(f) Cope rearrangement of a 1,5-diene4 marks
- 6(g) Diels–Alder reaction: product and reactants4 marks
- 6(h) IR distinction: hydrogen bonding and ring strain4 marks
- 6(i) McLafferty rearrangement: 2-pentanone and 3-pentanone4 marks
- 6(j) NMR assignment of 4-methylpent-1-yne4 marks