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  1. Practice problems
  2. Orgo 1
  3. Stereocenters and configuration
  4. Assigning the drawn acid

Organic Chemistry 1 · Stereocenters and configuration

Assigning the drawn acid

Interpret the evidence · Application

Conditions: Fischer convention: horizontal bonds point toward the viewer; vertical bonds point away. Condensed terminal groups retain the indicated connectivity.

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← All Stereocenters and configuration problemsNext problem: R or S for L-alanine from its Fischer projection →

The question

Assign the configuration at the central carbon in the displayed lactic-acid projection.

Reveal the answer and explanation

Answer and explanation

  1. Correct answer S.

    OH > CO₂H > CH₃ > H; the clockwise page order is inverted because H points toward the viewer.

  2. Not this one R.

    This is the uncorrected page result; priority 4 is horizontal rather than pointing away.

  3. Not this one No descriptor is possible because CO₂H and CH₃ both start with carbon.

    Their next-atom lists distinguish the carbon ligands.

Worked solution

O in OH gives priority 1. The carboxyl carbon compares as [O,O,O], beating methyl [H,H,H], giving priorities 2 and 3. H is priority 4. Since H is horizontal, invert the clockwise page trace to obtain S.

What you'll practice

Use the Fischer viewing convention to obtain an absolute descriptor.

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Tags

  • #FischerProjections
  • #RSConfiguration

More Stereocenters and configuration problems

  • Repairing a projection argument
  • Ranking isotopically labeled ligands
  • First-point-of-difference comparison
  • Assigning a substituted alkene
  • Comparing two directions around a ring
  • Choosing a legal Fischer manipulation
  • A descriptor after rotating the molecule
  • Checking whether E/Z is defined

Keep practicing

  • Stereocenters and configuration: practice problems
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