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Question:

Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to decolourize the colour of bromine?

Solution:

The correct option is D. The tert-BuONa acts as a base and gives an elimination product. The molecule in the fourth option does not give an unsaturation test because it does not contain a double bond after the reaction with tert-BuONa.