Dat destroyer orgo questions - num 72

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Mrhyde

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Question number 1)

Number 72. ) I have read that Aldo condensations can undergo spontaneous dehydration Even when heat is not listed as a next step. Aldos can dehydrate under acidic, basic, or thermal (heat) ......So I picked answer E , the conjugated , dehydrated more stable form as the Major product----------But the answer chosen as correct was D, the hydrated form.


Question number 2)

Also I know for b-dicarbonyl, the middle Carbon is the most Acidic..... But what about for this : http://wtt-pro.nist.gov/wtt-pro/image.png?cmp=2-pentanone

Which alpha carbon is the most acidic ? the carbon to the outter left of the carbonyl or the carbon in the middle ?

Question number 3)

- Even though I got number 95 correct on the Organic DAT Destroyer pg. 31 , -----> I know that the NBS removes off a benzylic hydrogen and replaces it with a BR but what if we had this :
https://s31.postimg.org/xwpi1b8bv/question_1.png
Would the BR attach to the first available benzylic hydrogen OR would it prefer the tertiary position even though its not the first hydrogen closest to the benzene ?
 
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