[lutesium]

Can you list them in an order from more Basic to the Acidic???

[fawad0418]

carbon 1

[lutesium]

What do you mean by Carbon 1??? Oxygen 1???


Lutesium...

[orgopete]

As written, this question is difficult to answer. Semantically, the oxygen atoms are bases (as written). Secondly, this problem raises another problem. A beta-keto aldehyde is normally found as its enol (and thus an acid). A nitro group will greatly increase the acidity. Sodium borohydride will react with a carboxylic acid to form hydrogen gas and the salt of the acid. If this reaction were to occur in this case, it would not reduce the aldehyde, but simply form a salt.

Let us assume that was not anticipated. In that case, I would expect the carbonyl groups to be reduced in the following order: 6>5>4>3>2>1. My prediction is based upon carbonyl reactivity. As electron density is removed from a carbonyl group by a halogen (acid chloride) or increased by a nitrogen (a carboxamide), the carbonyl reaction is increased or decreased, respectively. I am guessing on the effect of the amino group for 1, 2, and 3. An amino group is a slightly better electron withdrawing group than a hydrogen (pKa of ammonia, ~38, hydrogen ~36). However, because the amino groups are basic, they may (and should be) protonated. If they are ammonium groups, they will also activate the carbonyl groups relatively to a hydrogen. (If the nitrogen atoms are not protonated, they will condense with the carbonyl groups. That could be avoided by making them dimethylamino groups.)

[vhpk]

I've got the same answer with orgopete, C6 is the C of aldehyde group, with -NO₂ as a strong electronwithdrawing group, so the C becomes more electrophilic and it has the largest tendency to get the hydrogen from BH₄^-, although C5 has 2 electronwithdrawing group but due to the nitro group here is quite large and the steric effect makes BH₄^- difficult to get access to C. With the rest Cs, no electronwithdrawing group, so Cs aren't so electrophilic as C6, therefore C6 is most likely to react.
I have one problem that needs your help:
Why does LiAlH₄ reduce C=O but not C=C, it only reduces C=C in case of conjugation between C=C and C=O ?
Thank you

[fawad0418]

yes orgopete is right....