Smith 3rd Ed. (2010)
CH 24: Carbonyl Condensation Reactions

Solutions can be seen at

  1. Problem # 743

    Enolates are nucleophiles and react with a variety of electrophiles.

    Carbonyls are electrophiles. But aldehydes/ketones and  esters/acid chlorides often form different products.


    Use curved arrows to draw a mechanism for each reaction below. How do the two products differ?

  2. Problem # 746

    Show what combination of aldehyde, ketone, and/or ester can prepare each compound below. Every compound is a Claisen or aldol product.

  3. Problem # 747

    Show a combination of enolate (nucleophile) and electrophile that can produce each compound below.

    Remember that all enolates come from carbonyls.

  4. Problem # 749

    Show how to prepare each compound below from propanal. I've marked the "cuts" for you.

  5. Problem # 750

    Let's work through a Robinson annulation.

    Work backwords to determine the starting materials needed to produce each intermediate below, then show a mechanism for the overall reaction.