Organic, identify A and B in the following reaction
Reactant (shown in picture) + KCN gives A
A + H2/Pd gives B
24 Replies
@Dexter
Note for OP
+solved @user1 @user2... to close the thread when your doubt is solved. Mention the users who helped you solve the doubt. This will be added to their stats.now my book says that
throughout both A and B, the carbonyl bond is just unharmed
no CN nucleophilic reaction on the carbonyl, no reduction by H2/Pd to alcohol
why
H2/Pd should reduce tho?
i agree
welp, book problem
will CN attack =O in the first step?
they didnt specify a quantity like excess, or 1 equivalent
also if it does, does H2/Pd do anything to an alcohol
Now that I think about it, there are two electron deficient centres here, but figuring out where attack occurs is a matter of numbers
why not
🥁
both
Cl is definitely an easier spot to access
but if this comes in boards i do wanna know what to write
Sorry, but related question: could the -NH2 formed by H2/Pd then attack C=O to make 6-membered ring or something?
ooh
very interesting
it'd have to go out of the cyclohexane's plane for that to happen fs
NH2?
I am confused where an amine came from
Cl gets replaced by CN
which gets replaced by CH2NH2
Ye. the thing where we get like C=NHZ ig
Oh it's A+H2/Pd
I'm effing dumb
can the carbon linking the cyclohexane ring and the chain act as a pivot for the chain to rotate to form a 6 membered ring
or is that some form of strain
Something to do with cyclohexane steroechemistry?
ooh yes the topic i skipped
+1
Ok, so, CN will attack carbonyl, but cyanohydrin cannot form because no H(+)
can H2/Pd take care of that
Nope
Separate steps
You have a nitrile already
mm oke
so the O(-) formed would just resonate back to =O kicking out the CN?
is CN a good leaving group
ok its not but for a board question im probably overthinking it
No, but it doesn't have a choice
can a O(-)--C---CN not exist in peace
i guess not resonance is pretty strong
well this was fun, thanku
+solved @Opt
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