Q.Starting from CH₃MgI, how will you prepare the following? i) Acetic acid ii) Acetone iii) Ethyl acetate iv) Isopropyl alcohol v) Methyl cyanide

Step 1 (i) Acetic acid. CH3MgI reacts with solid CO2 (dry ice), giving an addition product that on hydrolysis (H+/H2O) gives acetic acid: CH3MgI + CO2 gives CH3-CO-OMgI, then + H2O/H+ gives CH3COOH.

Step 2 (ii) Acetone. CH3MgI reacts with acetyl chloride (CH3COCl), ONE equivalent, giving (after hydrolysis) the ketone acetone: CH3MgI + CH3COCl gives CH3-CO-CH3 (acetone) + Mg(I)Cl.

Step 3 (iii) Ethyl acetate. CH3MgI reacts with ethyl chloroformate (C2H5O-CO-Cl), giving (after hydrolysis) the ester ethyl acetate: CH3MgI + C2H5OCOCl gives CH3-CO-OC2H5 (ethyl acetate) + Mg(I)Cl.

Step 4 (iv) Isopropyl alcohol. CH3MgI reacts with acetaldehyde (CH3CHO, an aldehyde other than formaldehyde), giving (after H2O/H+ hydrolysis) the secondary alcohol isopropyl alcohol: CH3MgI + CH3CHO gives (CH3)2CH-OH. …

Work through the reagent list needed for each named target: CO2 for the acid, an acid chloride (one equivalent) for the ketone, a chloroformate for the ester, an ald …

• Using excess CH3MgI for the acetone target (ii) -- with excess reagent, the acid chloride's ketone intermediate reacts on to a TERTIARY alcohol instead; isolatin …