Substrate Control of Stereochemistry: Models for Facial Selectivity · seed 1 · A4, ink-friendly. The answer key prints on its own page for grown-ups.

Which face gets attacked

Science · Chemistry · ages 22-23
Name ______________________   Date ____________
  1. What does a chelating metal do to the substrate shape?

    • It destroys the stereocentre
    • It locks the new shape
    • It removes the carbonyl
  2. What does the standard open-chain model assume about the biggest neighbour?

    • It sits away from the carbonyl
    • It sits on top of the carbonyl
    • It bonds to the reagent
  3. On a rigid ring, attack direction is predicted from axial and equatorial approach arguments.

    Circle one:   True   False

  4. Adding a chelating metal flips the major product. What happened?

    • The reagent changed its charge
    • The other face opened
    • The stereocentre was erased
  5. An alpha-substituted aldehyde meets hydride with no metal present. Which product dominates?

    • The one from attack on the more blocked face
    • An equal mix of both diastereomers
    • The one from attack on the less blocked face
  6. A rigid cyclic ketone can be attacked from above or below the ring. How do you choose?

    • Always pick attack from above
    • Flip a coin, both are equal
    • The less clashed path
  7. A student applies the open-chain model to a chelated substrate and is surprised. What is the error?

    • Using a model the conditions break
    • Drawing the carbonyl at the wrong angle
    • Forgetting to stir
  8. Two models predict opposite faces. Which experiment distinguishes them?

    • Add or omit the metal
    • Run it twice as long
    • Use twice as much reagent
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Answer key

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

Which face gets attacked W1-mt_qLBmyLq2ZU-s1

  1. It locks the new shape · Gripping both oxygens freezes a different conformation.
  2. It sits away from the carbonyl · The model lines the biggest group away, leaving one face open.
  3. True · Rings cannot rearrange, so the approach path decides.
  4. The other face opened · Chelation freezes a new conformation with the other face open.
  5. The one from attack on the less blocked face · The open-chain model sends attack to the accessible face.
  6. The less clashed path · Axial and equatorial approach arguments name the clearer path.
  7. Using a model the conditions break · Each model rests on an assumption, and chelation breaks the open-chain one.
  8. Add or omit the metal · The models disagree exactly where chelation matters, so that comparison decides.
Worksheet · LightMySky