Few Questions:

Q1: On applying alkali solution followed by acidification which of the following gives lactone:

Q2: Give the end product of (A,B,C,D) when each of them is treated with base:

Q3: Arrange them in order of increasing acid strength:
acetic acid, Acrylic acid, HCl , α-cloro-acetic acid, formic acid

Will keep updating with more questions!
PS: Try to give reasons to support your answer.

9 Answers

19
Debotosh.. ·

ans 1 > c
ans 2> use favorski for A!
i will try the others later on..going for a tuition right now !

39
Pritish Chakraborty ·

Debo won't there be Favorski Rearrangement in C as well? Base abstracts proton, and 3 membered ring forms by SNi..
And in first question, lactone forms in c.

1
Unicorn--- Extinct!! ·

HCl>formic>acrylic>α-cloro-acetic acid

1
voldy ·

@ Q2
favorski for D ???

@Q1

C??? if u feel so give the mechanism

nice Q's by the way can somebody post the answers and their reasons preferably mechanism too .
Thank you

19
Debotosh.. ·

edited !

1
voldy ·

what about Q1 ??

1
Ankur ·

Answer for Q1 is not (c).. can you tell Srinath what you thought in this? Please give mechanism if you can. I'm confused in that... I did this earlier but now while revising I couldn't do *sigh* . @Debotosh: right.. Q2: we can do Favorskii in first.. in second I think it will be done by 3 membered ring breakage which will be formed just like it did in A .. but in C and D.. what do you think? Favorskii or not?

39
Pritish Chakraborty ·

Just a crazy idea :P

Ans would be (A) if this works..

And btw in the Favorskii question only (A) and (B) give the Favorskii reaction. A substrate of the form Ph-CH2-CO-CH2-X where X is F, Cl, Br, I is called a Favorskii reagent.

3
rocky ·

3.......
HCl>formic acid>α-cloro-acetic acid>acetic acid> Acrylic acid

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