3. Identify the reagents you would use to convert 1-bromopentane into each of the following compounds: (a) Pentanoic acid (b) Hexanoic acid (c) Pentanoyl chloride (d) Hexanamide (e) Pentanamide (f) Ethyl hexanoate

Explanation:

a )

CH₃CH₂CH₂CH₂CH₂Br + KOH   ⇒ CH₃CH₂CH₂CH₂CH₂OH

CH₃CH₂CH₂CH₂CH₂OH  + acidic potassium dichromate ⇒  CH₃CH₂CH₂CH₂COOH

b )

CH₃CH₂CH₂CH₂CH₂Br + KCN ⇒ CH₃CH₂CH₂CH₂CH₂CN  Hydrolysis ⇒ CH₃CH₂CH₂CH₂CH₂COOH .

c )

CH₃CH₂CH₂CH₂CH₂Br + KOH   ⇒ CH₃CH₂CH₂CH₂CH₂OH

CH₃CH₂CH₂CH₂CH₂OH  + acidic potassium dichromate ⇒  CH₃CH₂CH₂CH₂COOH + SOCl₂ ( thionyl  chloride ) ⇒ CH₃CH₂CH₂CH₂COCl

d )

CH₃CH₂CH₂CH₂CH₂Br + KCN ⇒ CH₃CH₂CH₂CH₂CH₂CN  Hydrolysis ⇒ CH₃CH₂CH₂CH₂CH₂COOH + PCC ( NH₃ ) ⇒ CH₃CH₂CH₂CH₂CH₂CONH₂

e )

CH₃CH₂CH₂CH₂CH₂Br + KCN ⇒ CH₃CH₂CH₂CH₂CH₂CN  Hydrolysis ⇒ CH₃CH₂CH₂CH₂CH₂COOH + C₂H₅OH ( Ethyl alcohol + H⁺ )⇒  

CH₃CH₂CH₂CH₂CH₂COOC₂H₅ ( ethyl hexanoate )

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