Which of the following option regarding issue and redemption of debenture is not possible in general?

Issued at discount, Redemption at discount

The correct answer is Option (2) - Issued at discount, Redemption at discount.

Redemption of debentures means discharge of liability on account of debentures by repayment made to the debenture holders. Debentures can be redeemed either at par or at a premium. Depending upon the terms and conditions of issue and redemption of debentures, the following six situations are commonly found in practice.
(i) Issued at par and redeemable at par
(ii) Issued at discount and redeemable at par
(iii) Issued at a premium and redeemable at par
(iv) Issued at par and redeemable at a premium
(v) Issued at a discount and redeemable at a premium
(vi) Issued at a premium and redeemable at a premium.

*DEBENTURES CANNOT BE REDEEMED AT DISCOUNT.