Compound A is 5-oxohexanal. One mole of A is reacted with one mole of CH ₃ MgBr in ether followed by hydrolysis with water to give major product B. Compound B is then treated with an excess of I ₂ and NaOH , followed by acidification, to yield compound C. The number of moles of NaOH required to completely neutralize 1 mole of compound C is _______.

Step-by-step solution

Step 1: Compound A is 5-oxohexanal, which contains both an aldehyde and a ketone group. Aldehydes are more electrophilic and sterically less hindered than ketones. Thus, 1 equivalent of CH ₃ MgBr selectively attacks the aldehyde group. After hydrolysis, the major product B is 6-hydroxyheptan-2-one. Step 2: Compound B is treated with excess I ₂/ NaOH (haloform reagent). The reagent first acts as an oxidizing agent, oxidizing the secondary alcohol at C6 to a ketone, forming heptane-2,6-dione. Step 3: Heptane-2,6-dion