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
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) $\endgroup$– shreyaCommented Jul 27, 2020 at 17:36
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1$\begingroup$ 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. $\endgroup$– user55119Commented Jul 27, 2020 at 19:17
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1$\begingroup$ 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 SURESHCommented Jul 28, 2020 at 5:00
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$\begingroup$ 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 SURESHCommented Jul 28, 2020 at 5:01
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$\begingroup$ Shreya why would it be geminal ? $\endgroup$– Aditya SURESHCommented Jul 28, 2020 at 20:56
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1 Answer
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Considering the follow up doubt, why geminal and not vicinal?
the carbocation formed is more stable because of $\ce{Cl}$ +M.
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1$\begingroup$ also make sure you dont use this logic anywhere else, this is an observation specific as theres +M and -I continuously fighting. $\endgroup$– shreyaCommented Jul 29, 2020 at 10:20