Strategy in Retrosynthesis: Strategic Bonds and Convergent Routes · seed 1 · A4, ink-friendly. The answer key prints on its own page for grown-ups.

Planning the way back

Science · Chemistry · ages 22-23
Name ______________________   Date ____________
  1. What does symmetry buy in a synthesis plan?

    • Fewer distinct steps
    • Larger reaction flasks
    • Faster stirring
  2. How should candidate disconnections be ranked?

    • By skeletal simplification
    • By how easy each is to draw
    • By how many steps each adds
  3. A convergent route joins fragments of similar size late in the synthesis.

    Circle one:   True   False

  4. A cut you want is blocked by the group sitting there. What opens it?

    • Heating the flask longer
    • Swap the group first
    • Adding more solvent
  5. Two steps run at 0.9 yield each. What is the overall yield?

    Answer: ______________

  6. Two routes use the same steps. One runs six steps in line, the other joins two three-step branches. Which gives more product?

    • The six-step line, it looks simpler
    • Both give exactly the same
    • The branched route
  7. Two branches are ready: one took two steps, the other took seven. What should you suspect?

    • The long branch sets the loss
    • The short branch must be wrong
    • Branch lengths never matter
  8. Handed a polycyclic target, a student cuts a side chain first. What is the strategic error?

    • Side chains are never cut
    • Almost no simplification
    • Rings must never be split
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Answer key

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

Planning the way back W1-mt_9ZRKVbdP72-s1

  1. Fewer distinct steps · One operation can install the same feature twice.
  2. By skeletal simplification · Strategy means cutting where the skeleton simplifies most.
  3. True · Balanced branches joined late keep the longest line short.
  4. Swap the group first · Swapping the group can unblock the disconnection.
  5. 0.81 · Multiply the step yields: 0.9 times 0.9 is 0.81.
  6. The branched route · Fewer multiplications on the longest line leave more product standing.
  7. The long branch sets the loss · Convergent routes win when branches stay balanced; a seven-step branch drags like a linear route.
  8. Almost no simplification · Strategic bonds are the ones that simplify the skeleton most.
Worksheet · LightMySky