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I want to ask about nucleophilic attack by Cl in Step 2.
To me there seem 4 electrophilic sites and I marked them as (a)~(d).
mechanism I've seen in lecture only deals with site (a).

maybe (c) is less electrophilic and (d) makes this reaction go backwards, so I can get past them. but when Cl- attacks (b), it could break a bond b.w (b) and (d), resulting in completely different product, as well as a bond b.w (a) and (b).

so my question is,
is nucleophilic attack on site(b) by Cl- resulting in breaking bond b.w (b) and (d) possible? if so, to what extent? if not, why?

hope somebody teach me something!!

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    $\begingroup$ Just draw the possible products from attack on (b) and breaking either of the (b-d) or (b-a) bonds. Do they look likely to form? $\endgroup$
    – K_P
    Apr 4, 2016 at 9:20
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    $\begingroup$ Um... maybe I ignored high electronegativity of O that wouldn't allow breaking these 2 bonds? $\endgroup$
    – NK Yu
    Apr 5, 2016 at 7:23

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