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Chirality and Stereochemistry Practice Quiz

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Chirality and Stereochemistry R S Enantiomers Diastereomers Meso Tutorial SeriesThe key to mastering chirality and stereochemistry is through practice, practice, and more practice. But where do you get all those practice problems?

After reviewing the videos in my Chirality and Stereochemistry series, and working through the simple questions in each, see how well you’ve mastered the material by trying my Stereochemistry Practice Quiz below.

The questions range from medium to tricky to ENSURE you are comfortable looking out for those tricks. Be sure to review the videos first and follow along with the Stereochemistry Cheat Sheet.

(scroll down for the PDF solutions)

Stereochemistry Practice Part 1

Determine if the following molecules are optically active (chiral) or optically inactive (achiral)

Stereochemistry Practice Questions Chiral Achiral

Stereochemistry Practice Part 2

Rank each set of substituents from high to low priority using Cahn-Ingold-Prelog ranking rules.
Hint: Need help ranking? See Chirality video 2

Stereochemistry Practice Cahn Ingol Prelog Ranking Rules

Stereochemistry Practice Part 3

Label every chiral carbon on the following molecules

Stereochemistry Practice Quiz Chiral Centers

Stereochemistry Practice Part 4

Name the following compounds. Be sure to include Absolute Configuration (R/S) as applicable

Hint: Need a review on naming? See the Naming Organic Compounds video series

Stereochemistry Practice finding R and S configuration(1)

Stereochemistry Practice Part 5

Draw the enantiomer for each of the following chiral molecules

Stereochemistry Practice quiz finding R and S

Stereochemistry Practice Part 6

Draw the following molecules clearly indicating every chiral center

  1. (S)-3-phenylpentanoic acid
  2. (R)-3,3-dimethyl-2-butanol
  3. (3R,4R)-3,4-dihydroxy-2-pentanone

Stereochemistry Practice Part 7

Find the absolute Configuration (R/S) for the following chiral compounds

Hint: Need a review on finding R and S? See videos 2-4 in the Chirality Series

Stereochemistry Practice finding R and S chirality

Stereochemistry Practice Part 8

Find the relationship between each molecule pair. Choose from:

  • Identical / same compound
  • Constitutional isomers
  • Enantiomers
  • Diastereomers
  • Meso compounds
  • Completely unrelated

Stereochemistry Practice Chirality R and S a

Stereochemistry Practice Chirality R and S b

Stereochemistry Practice Chirality R and S c

Stereochemistry Practice Chirality R and S d

Stereochemistry Practice Chirality R and S e

Stereochemistry Practice Chirality R and S f

Stereochemistry Practice Chirality R and S g

Stereochemistry Practice Chirality R and S h

Stereochemistry Practice Chirality R and S i

Stereochemistry Practice Part 9

Find the absolute configuration (R/S) for each chiral center on the following molecules. Hint: There may be more than 1 chiral carbon per molecule.

 

Stereochemistry Practice Chirality R S aStereochemistry Practice Chirality R S bhttps://leah4sci.com/r-and-s-configuration-using-cahn-ingold-prelog-priority-rules/Stereochemistry Practice Chirality R S d Stereochemistry Practice Chirality R S eStereochemistry Practice Chirality R S fStereochemistry Practice Chirality R S gStereochemistry Practice Chirality R S hStereochemistry Practice Chirality R S i

 

Stereochemistry Practice Part 10

Draw all possible stereoisomers for each of the following:

  1. 1,3-dibromocyclopentane
  2. 3,4,5-trimethyl-2-hexanone
  3. 3-isopropyl-4-methyl-2-pentanol
  4. 4-ethyl-3-methylhexanoic acid

Ready to see how you did? Grab the PDF solutions below

Send Me The solutions >>

Comments

  4. Thanks for your resources they’re great! I’m confused about 1 thing… when do we use the swapping (ie. 2 swaps = same molecule) to determine R/S and when would we use just the switching to the opposite configuration when the lowest priority group is in the front??

    Reply

    • One swap is the opposite. Two swaps gives you the same chirality.
      If you do one swap, you have to remember to switch S to R or R to S. Sometimes I will forget that I only made one swap, therefore to avoid mistakes, I always do two so the chirality is the same.

      Reply

  5. why is (part 1 / a)) achiral? it has an H, ethyl, isobutyl and the Et (i don’t know what that means my the way :D), maybe it got something to do with that, because I am form Germany.

    Reply

    • The ethyl group thats visible and the Et that is branched are actually both ethyl groups. That means this molecule only has three unique substituents making it achiral. I purposefully drew it this way so that you are not fooled when your professors try to pretend you have four unique groups but there are actually only three, like in this question.

      Reply

  9. *sad* can’t get the PDF solution coz I live in Africa. Pleasssssee Leah is it possible to send it to my email. Your site is the bomb!!! telling all my friends about it.

    Reply

    • You should be able to get the PDF anywhere in the world unless your computer is blocking the email Jaey

      Reply

  13. these are awesome problems!! they have so much diversity and cover all aspects of all possible “tricky”questions. Please put up the solutions

    Reply

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