Can anyone tell me where I am doing it wrong for the following reaction?
In the first step, Br should be attached to the alpha carbon.
In second step, the bromide is replaced by cyanide.
I am able to get the third product that is final compound.
Can anyone tell me where I am doing it wrong for the following reaction?
In the first step, Br should be attached to the alpha carbon.
In second step, the bromide is replaced by cyanide.
I am able to get the third product that is final compound.
Step 1: $\alpha$-bromination $$\ce{CH3-COOH + Br2/P -> Br-CH2-COOH}$$
Step 2: Nucleophilic Substitution by Sodium Cyanide $$\ce{Br-CH2-COOH + NaCN -> NaBr + NC-CH2-COOH}$$
Step 3: Acid-catalyzed Conversion of Nitrile to Amide or Acid
(1) First hydration... $$\ce{NC-CH2-COOH + H2O -> H2N-CO-CH2-COOH}$$ (2) Further heating... $$\ce{H2N-CO-CH2-COOH -> HOOC-CH2-COOH + NH4+}$$
Special Notes
Be VERY CAREFUL with Step 2 as you are potentially forming $\ce{HCN}$ which could get everyone in the lab killed if you're not careful.
There are two possibilities. You will have a two step reaction
NC-CH2COOH -> HOOC-CH2-COOH This is malonic acid. It can be further decarboxylated to
HOOC-CH2-COOH + H$^+$ + heat -> CO2 + CH3COOH
the final product is acetic acid.