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1,4 conjugate addition vs 1,2 conjugate addition
ChanC
#1 Posted : Wednesday, June 08, 2011 4:28:29 AM
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Hi,

I was doing question 591 in the 1001 booklet and I spotted the options 1,4 and 1,2 conjugate addition. Do we need to know this and if so what is it and where is it used in? Your reply is greatly appreciated.
mathewchui
#2 Posted : Wednesday, June 08, 2011 6:46:22 AM
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That's a really good question.

If you look at page 61, you'll see that "conjugate addition" is italicized, meaning it is nice-to-know but not need-to-know.

A brief explanation. "1,2-anything" usually means something happening between two adjacent carbons. For example, 1,2-diol is two alcohol groups next to each other; C(OH)-C(OH).

By contrast, a 1,4-diol is C(OH)-C-C-C(OH).

You shouldn't need to know the precise definitions of "conjugate addition" to answer this question. Just recognize that the reaction is nucleophilic in nature (CN as a nu) and cross out C. Recognize that this is not a substitution, because there is no leaving group or anything of that nature and cross out D. You should recognize that H and CN are added onto product D and so this must be addition of some sort (compare product D versus product E to see this is true).

Then it's just a matter of logic. The H and CN are added C(H)-C(CN), which is a 1,2 arrangement. Even without knowing that notation, hopefully you'll guess that it looks more like a 1,2 than a 1,4 addition.

And if it comes to it, you've got a multiple guess between A versus B. 50% chance is better than 25%
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