Organocatalysis: Enamine and Iminium Activation · seed 1 · A4, ink-friendly. The answer key prints on its own page for grown-ups.

Small amines, big activation

Science · Chemistry · ages 22-23
Name ______________________   Date ____________
  1. What does an iminium intermediate do to the beta carbon?

    • It shields it from all attack
    • It makes it more electrophilic
    • It turns it into a base
  2. An amine condenses with a ketone to give an enamine. Which position is activated?

    • The beta carbon as an electrophile
    • The alpha carbon as a nucleophile
    • The oxygen as a leaving group
  3. After its step, the amine catalyst is released unchanged and can cycle again.

    Circle one:   True   False

  4. Turnover is sluggish although binding is fast. What is the likely choke point?

    • Release of the catalyst after the step
    • Weighing out the starting aldehyde
    • Choosing the flask size
  5. A chiral pyrrolidine blocks the top face of its enamine. Where does the partner attack?

    • The top face, through the shield
    • Neither face, the reaction stops
    • The open bottom face
  6. A drug intermediate must contain no metal traces. Which route fits?

    • A palladium-catalysed route with extra ligands
    • The small-amine organocatalytic route
    • A route with two different metals
  7. An aldehyde plus a chiral amine gives racemic product. What does that tell you?

    • It shielded neither face
    • The aldehyde was too pure
    • Water was missing from the flask
  8. A student draws attack on the shielded face and predicts the wrong mirror image. What fixes the prediction?

    • React through the open face
    • Doubling the catalyst loading
    • Heating the mixture harder
LightMySky · lightmysky.comW1-mt_E3lmwAFuIO-s1

Answer key

For grown-ups. Fold this page away before handing over the rest.

Small amines, big activation W1-mt_E3lmwAFuIO-s1

  1. It makes it more electrophilic · Iminium activation targets the beta carbon as an electrophile.
  2. The alpha carbon as a nucleophile · The enamine makes the alpha carbon nucleophilic.
  3. True · Release without change is what makes it a catalyst.
  4. Release of the catalyst after the step · Fast binding with slow cycling points at sluggish release.
  5. The open bottom face · The blocked face is shut, so attack lands on the open one.
  6. The small-amine organocatalytic route · The amine route leaves no metal behind by construction.
  7. It shielded neither face · No enrichment means neither face was effectively blocked.
  8. React through the open face · The sense of induction follows the open face, not the shielded one.
Worksheet · LightMySky