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

The correct option is Issued at discount, Redemption at discount.

Let us break down the concepts of the issue and redemption of debentures to understand why this scenario is not possible in general:
1. Issue of Debentures: A company raises capital by issuing debentures. These debentures can be issued at par (at face value), at a premium (above face value), or at a discount (below face value).
2. Redemption of Debentures: Redemption refers to the repayment of the principal amount of the debentures to the investors upon maturity. Debentures can be redeemed either at par (repaying the face value) or at a premium (repaying more than the face value to provide an extra return to the investors).

Why is "Redemption at a discount" not feasible?
Redemption at a discount implies that the company would repay an amount less than the nominal (face) value of the debenture at maturity. From an investor's perspective, purchasing a debt instrument that pays back less than its face value upon maturity is commercially unacceptable. If a debenture is both issued at a discount and redeemed at a discount, it would result in a double loss for the investor. Therefore, companies cannot practically or legally issue debentures with a clause stating they will be redeemed at a discount.

Hence, the combination of Issued at discount, Redemption at discount is not possible in general business practice.