Hello,
1. Yes, the distribution of assets on liquidation by a company will be deemed to be a dividend to the extent it has the balance of accumulated free reserves and the company will have to pay dividend distribution tax (DDT) on the same.
2. The shareholder will be liable to capital gains both times. Shareholder on the liquidation of a company receives any money or other assets from the company, he shall be chargeable to income-tax under the head "Capital gains", in respect of the money so received or the market value of the other assets on the date of distribution, as reduced by the amount assessed as dividend within the meaning of section 2(22)(c) (as stated in point no. 1) and the sum so arrived at shall be deemed to be the full value of the consideration for the purposes of section 48. And further, if the asset (other than cash) acquired by the shareholder, at the time of liquidation, is subsequently transferred by the shareholder; then for the purpose of computation of capital gain of such transfer, the cost of acquisition of such asset shall be the market value of the asset on the date of distribution.
I hope that this answer satisfies your requirements.
Regards,
CA Hunny Badlani