My question: (though it won't alter the product)
Which carbon is attacked first, the one adjacent to sulphur or the one adjacent to oxygen?
The solution says that the carbon adjacent to sulphur is attacked first. I don't understand why.
According to me, sulphur is less electron withdrawing than oxygen (electronegativity decreases down the group), so the carbon adjacent to oxygen must be more electrophilic.
Could someone please explain as to why attack should first occur at the carbon adjacent to the sulphur atom? (or is the solution incorrect?)
P.S. Here, due to syn stereochemistry (NGP is not favourable) choice of electrophilic centre undergoing attack first doesn't influence the product at all. However, in the case where the sulphur and oxygen atoms are anti with respect to the ring, and NGP is a possibility, and then the products would greatly differ (depending on whether attack first happens on carbon adjacent to oxygen or sulphur)
Source: MS Chouhan; Advanced Problems In Organic Chemistry; 11th ed; Q35 in Chapter Alcohols, Ether, and Epoxides