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Question

$$\ce{CH3-CH(Cl)-CH(Cl)-COO- ->[-CO2]A->[HCl]B->[aq KOH]C}$$ Product C is:

a) $\ce{CH3-CH2-CHO}$

b) $\ce{CH3-CH(OH)-CH2-CH2-OH}$

c) $\ce{CH3-CHO}$

d)$\ce{CH3-C(=O)-CH3}$

Answer

The answer given is (a)

My attempt

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Where did I go wrong?

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  • $\begingroup$ the addition of HCL youve done to alkene is wrong , it will be geminal not vicinal there by making ans (a) $\endgroup$ – shreya Jul 27 '20 at 17:36
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    $\begingroup$ The answer is a) as long a propionaldehyde can avoid an aldol condensation in the presence of aqueous KOH. c) can't be the answer. Do the math on the number of carbons. $\endgroup$ – user55119 Jul 27 '20 at 19:17
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    $\begingroup$ Yeah the answer is A my bad( i will edit it). But why where would the H+ attack(in the 2nd step)? I thought as i did because Cl- would make C+ unstable? $\endgroup$ – Aditya SURESH Jul 28 '20 at 5:00
  • $\begingroup$ Also can someone advice me how to convert pictures to text like the above text ? I will try to make my questions better. $\endgroup$ – Aditya SURESH Jul 28 '20 at 5:01
  • $\begingroup$ Shreya why would it be geminal ? $\endgroup$ – Aditya SURESH Jul 28 '20 at 20:56
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Considering the follow up doubt, why geminal and not vicinal? geminal di halide formation

the carbocation formed is more stable because of $\ce{Cl}$ +M.

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    $\begingroup$ also make sure you dont use this logic anywhere else, this is an observation specific as theres +M and -I continuously fighting. $\endgroup$ – shreya Jul 29 '20 at 10:20

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