(a) Write the reaction of `RCOOH` with `conc.H_2 OS_4` forming two possible cations.
(b) Give the relative stabilities of the cations.
( c) Which cation undergoes `(C-O)` bond cleavage more readily ?
(d) Calculate the van't Hoff factor, `i` (number of moles of particles formed per mole of solute), in both cases.

Explanation

(a)
(b) `(II)` is more stable and is the major cation since it has equal resonance contributing structures.
`[R-overset(.^(o+):OH)overset(||)(C)-OHharrR-overset(ddot:OH)overset(|)(C)-overset(o+)underset(..)OH]`
( c) `(I)` is more reactive. It forms acylium ion `(RC -= O^(oplus))` by losing `H_2 O`.
(d) If `(I)` is formed, it would lose `H_2 O`, which would accept `H^(oplus)` from `H_2 SO_4` , thus the net reaction and `i` would be :

If `(II)` is formed, the net reaction and `i` would be :

The experiment shows `i = 2`.