EK 1001 orgo q. 579

[korsibor]

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As I go further this book kinda confuses me a lot.

For question #579 , can't there be self aldol condensation for product D , that is D reacting with anoth D, and a cross condensation between 2,2-dimethylbutanol? I thought two products are possible.Or is it because the question asks for the TRUE product that is why the answer is 1?

Also, i'm having some difficulty differentiating electrophilic substitution from nucleophilic substitution. Is elctrophilic when an electrophile is doing the attacking and vice-versa?

 

[loveoforganic]

Honestly, you would probably get that product, but it would be a very small quantity for these reasons -

1) Your base catalyst is going to have deprotonated and thus deactivated only some of Product D, so you'll have a larger amount of the 2,2-dimethylbutanal to react with.

2) Aldehydes are more reactive to nucleophilic substitution than ketones are due to inductive reasons.

For your second question, yes, that's the difference.