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Chirality and Stereochemistry Practice Quiz

August 28, 2022 By Leah4sci 78 Comments

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!

Filed Under: Organic Chemistry Practice Problems Tagged With: chirality, enantiomers, quiz, r and s, stereochemistry

Comments

  1. Ali says

    April 8, 2019 at 7:28 am

    In solution paper answer of 10(part-3and 4) is missing.

    Reply
  2. Peter wanjiru says

    November 25, 2018 at 8:44 am

    Hello .am great .the site is so resourceful.thankyou

    Reply
  3. eyob says

    November 16, 2018 at 4:22 pm

    i did not get the solution can you help me?

    Reply
  4. busiso says

    October 24, 2018 at 6:51 am

    sorry, i meant d part 8

    Reply
  5. busiso says

    October 24, 2018 at 6:49 am

    how did h on part 8 end to be identical. i keep getting diastereomers for my answer

    Reply
  6. Dilhani says

    August 3, 2018 at 2:15 pm

    Can I know why part 1 b is a chiral molecule. Do we just take the mirror image?

    Reply
  7. shanmuga niveditha says

    July 25, 2018 at 3:54 pm

    were do i get the answers?

    Reply
  8. Aniruddha says

    June 25, 2018 at 11:11 pm

    Great work dear.I will recommend this page to all my friends.

    Reply
  9. tami says

    June 1, 2018 at 5:06 pm

    Thanks for all your work – it’s really great! 🙂
    I’m confused about part 9 (d) – why is it R instead of S?
    Thanks

    Reply
  10. Sheida says

    April 14, 2018 at 12:37 pm

    Hi, Thank you so much for your amazing video, but where is the solution ? how I know if I am correct

    Reply
  11. leon says

    April 8, 2018 at 7:09 am

    how is 8(b) becoming diastereomers?

    Reply
  12. leon says

    April 8, 2018 at 6:47 am

    very helpful,but i dont get it on how you chose the relationship between molecules,,any further help????

    Reply
  13. Tara Donley says

    March 13, 2018 at 5:55 pm

    Why is (h.) in part 8 an enantiomer? There’s an ethyl group on one molecule and then a propyl group on the other. Can you explain please? Thank you so much!!

    Reply
  14. SARA says

    February 17, 2018 at 8:08 am

    i love u mam:)) becoz of u i was able to score good markss……

    Reply
  15. Julia Chahine says

    February 12, 2018 at 9:40 pm

    Why does NH2 have a higher priority than CN?

    Reply
  16. Brenda says

    January 25, 2018 at 7:44 pm

    Very helpful videos! Every explanation was very clear to follow, thanks a lot! Your swap method is awasome

    Reply
  17. Sania khan says

    January 13, 2018 at 1:08 am

    Best teacher ever

    Reply
  18. Pragati Pratishruti Swain says

    January 12, 2018 at 12:12 pm

    Thank you so much for the illusioning questions. Enjoyed doing them with mistakes! Please add question banks for reagents, structural elucidation, organic spectroscopy and name reactions also. Please, please , please!!!!

    Reply
  19. NAZ97 says

    December 26, 2017 at 4:45 am

    For some reason I can’t seem to find the solutions even after giving my email.

    Reply
  20. annabelle says

    December 13, 2017 at 5:03 am

    hi
    thank you so much! your a savior!

    about qu’ 1:
    why is a a-chiral??

    Reply
  21. Cris says

    November 28, 2017 at 3:37 pm

    Hi Leah. Thanks for the videos and material, they´re very helpful.
    I have a question in part 9 b). When I order the groups Nh3 is the #1, COO- is #2 and CH2OH is#3, but with this order gives me an R configuration and in the solutions is S. I watched again the video for “R and S configuration for Lengthy Complex Substituents” but i still don´t understand.
    Thanks again

    Reply
  22. Jayson Vega says

    November 26, 2017 at 2:36 am

    In part three problem one, why are there 3 chiral carbons if none of them have unique substituents?

    Reply
    • Jayson Vega says

      November 26, 2017 at 2:39 am

      my bad, I meant only one of them is chiral because it has unique substituents. The two other carbons that are not attached to the F do not have unique subtituents

      Reply
  23. Jane says

    November 23, 2017 at 6:21 pm

    Hi , i still havent receive my pdf solution , how ?

    Reply
  24. Salami Yusuff says

    November 14, 2017 at 1:13 pm

    I haven’t seen the solution PDFs since.

    Please, kindly help with the solution.

    Reply
  25. mame penda sarr says

    November 12, 2017 at 9:12 pm

    How is part 1 a) Achiral? If I try to flip it, it puts the ET in the back, so it doesn’t superimpose. Could you help me understand please?

    Reply
  26. lirim says

    November 6, 2017 at 6:59 am

    thank you so much Leah.I really found it helpful.Looking forward for new videos from you!

    Reply
  27. ian Koorsen says

    October 29, 2017 at 3:13 pm

    I already signed up and can’t get the solution… Why is everything and ad.

    Reply
  28. Zoë says

    October 10, 2017 at 4:12 pm

    I didn’t get the chirality cheat sheet when I gave my email. It just sent me the whole cheat sheet pdf, which doesn’t include chirality. Help please?

    Reply
  29. Jordan Jones says

    September 30, 2017 at 11:24 pm

    I don’t know if you are still active on this but i’m trying to get the pdf solutions but it won’t show up in any of my emails. Could you try sending it again?

    Reply
  30. Rachel Steger says

    September 24, 2017 at 10:33 am

    I am also having trouble with part 3, especially b and c. Could you please help me?

    Reply
  31. Rachel Steger says

    September 24, 2017 at 9:43 am

    I do not understand why 1e is achiral.. please help

    Reply
  32. junk says

    September 11, 2017 at 12:49 pm

    the solutions will never get emailed to you,dont waste ur time

    Reply
  33. Jyoti says

    September 3, 2017 at 5:13 am

    Vry nice mam..really helpful..gud job

    Reply
  34. Iris says

    August 16, 2017 at 3:46 pm

    Hey, love your website and the way you explai!

    I have a question to part 8 of the quize, question e). I am confused, if it’s just cis and trans, i should just flip the ring to get to the right konformation right? But everytime i flip the ring axial goes to equatorial. At the first Ring there is a and e but in the secon ring, they are both equatorial. How can that happen?

    Thank for your help.

    Reply
  35. Megan B says

    June 17, 2017 at 5:15 pm

    Using your rules, I got the opposite answers for 9b,d,i. All of these examples, H is going into page right?
    Also in 9h, what is the substituent group on the right that look like ]. Thanks in advance!

    Reply
  36. Akash Yadav says

    March 18, 2017 at 4:15 am

    Can you please explain the R,S configuration in part 4(b)?

    Reply
  37. Zoe says

    January 7, 2017 at 9:12 am

    Could you help me with why 9b is s not r, i have the substituents ranked n^+h3 > coo^- > ch2oh > h and because my h facing backwards this would give an r configuration, thanks

    Reply
  38. kurnish says

    January 4, 2017 at 10:39 am

    In part 4 question e, why did you name the compound N,N? And also in ques b of same part why is it 1R,2S? Isn’t it 1R,1S?

    Reply
  39. saumya says

    December 30, 2016 at 2:36 am

    Your videos are indeed a great help for those who want to master the topic.

    Reply
  40. Ronald DOnald says

    December 26, 2016 at 10:37 pm

    Part 9 Part b…. why is it not R configuration? NH3+ gets the #1 priority, COO- gets the number 2, and CH2OH gets the number 3 priority. Since H is on a dash, we can just go straight clockwise from 1 -> 2 -> 3

    Reply
  41. Taeyoung says

    December 12, 2016 at 4:35 am

    Having a lot of trouble seeing how part 5 c) works x_x

    Reply
    • Taeyoung says

      December 12, 2016 at 4:37 am

      How is the structure in the solution an enantiomer not a diastereomer?

      Reply
  42. Evelyn T says

    November 12, 2016 at 6:55 pm

    I’m sorry, the solutions for part one dont align when the answers I got on chirality. I dont understand what Im doing wrong.

    Reply
  43. ijaz says

    November 10, 2016 at 3:34 pm

    Which groups will be perpendicular to plan …horizontal or vertical???

    Reply
  44. Trisha says

    November 6, 2016 at 5:02 pm

    How come the newman projection is achiral? the front carbon is attached to three different things isn’t it?

    Reply
  45. chetan says

    November 1, 2016 at 2:13 am

    i love your work ….

    want to meet you…

    Reply
  46. Hannah Gyamfi says

    October 25, 2016 at 2:24 am

    This was very helpful. Is there a video made purposely for this quiz? I would love to see where and how I messed up on some questions.

    Reply
    • Leah4sci says

      December 29, 2016 at 5:34 pm

      Check out my Chirality and Stereochemistry Tutorial Video Series: https://leah4sci.com/chirality-stereochemistry-enantiomers-diastereomers-r-s-organic-chemistry-tutorial-series/

      Reply
  47. Zulqarnain Haider says

    September 1, 2016 at 3:25 pm

    practice was really helpful. Thanks a lot and really appreciate your work.

    Reply
    • Leah4sci says

      September 2, 2016 at 9:54 am

      Zularnain, so glad you found this helpful!

      Reply
  48. Betty says

    August 7, 2016 at 1:01 pm

    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
    • Leah4sci says

      August 12, 2016 at 10:53 am

      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
  49. Kim Kowalewski says

    July 28, 2016 at 7:46 am

    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
    • Kim Kowalewski says

      July 28, 2016 at 7:47 am

      or is Et a short term for ethyl? that this makes sence

      Reply
      • Kim Kowalewski says

        July 28, 2016 at 9:33 am

        you forgot to draw the two methyl groups at part 7, f).. otherwise there would be no chiral center

        Reply
        • Leah4sci says

          September 2, 2016 at 10:52 am

          7f only has one methyl group, or did you mean something else?

          Reply
          • Zarifa says

            October 26, 2016 at 6:45 pm

            I too was worried about this at first. In your practice problem there are no methyl groups in the first cyclopentane whereas in your answer sheet there are two methyl groups. When i did the problem without looking at the answer sheet, there wasn’t a chiral molecule. But in the answer sheet the C=O is S BECAUSE there are two methyl groups in the cyclopentane that wasn’t present in the practice problem.

    • Leah4sci says

      September 2, 2016 at 10:48 am

      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
  50. Arijit Das says

    April 25, 2016 at 4:42 pm

    Thanks for all this tutorials.it helped me lot .

    Reply
    • Leah4sci says

      May 3, 2016 at 8:46 am

      You’re welcome Arijit

      Reply
  51. israel boniface says

    April 20, 2016 at 3:50 am

    I like it. But no pdf notes?

    Reply
    • Leah4sci says

      April 20, 2016 at 8:44 pm

      Did you sign up for it Israel?

      Reply
  52. leyla says

    April 3, 2016 at 12:49 pm

    For Stereochemistry Practice Part 9 letter D:
    why is it not the S configuration? Cl gets the highest priority, afterwards the side closest to the double bond oxygen gets the next priority and then the side furthest from the double bond oxygen gets the 3rd priority and since H is in the back it makes a counterclockwise arrow and so should it not be S?
    I was running into the same problem with B as well.
    I’m not sure what I’m doing wrong, since my answers for B and D did not match the answer key.
    Also thank you for the amazing tutorials, I wish I found your site earlier!

    Reply
  53. Pamela Jane says

    March 14, 2016 at 1:09 pm

    Thank you so much! I am taking Orgo I right now and it helps me a lot. 🙂

    Reply
    • Leah4sci says

      April 4, 2016 at 5:47 pm

      Thanks Pamela, glad to help

      Reply
  54. jaey says

    March 2, 2016 at 2:44 am

    *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
    • Leah4sci says

      April 4, 2016 at 5:42 pm

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

      Reply
  55. busari says

    January 2, 2016 at 7:23 pm

    I love this…how I wished I had known this site before..ahhh

    Reply
    • Leah4sci says

      January 26, 2016 at 12:26 am

      Better late than never, right Busari? Share with your classmates so they don’t have similar regrets

      Reply
  56. chemistry1 says

    December 20, 2015 at 9:54 am

    THIS IS DIFFICULT !

    Reply
    • Leah4sci says

      January 2, 2016 at 6:45 pm

      That’s the point 😉

      Reply
  57. stephen says

    December 1, 2015 at 4:39 am

    you promised to send the pdf solution and its been a while since. Kindly please assist. thank you.

    Reply
    • Leah4sci says

      December 6, 2015 at 5:23 pm

      It should have arrived in your email inbox with 5 minutes. Check your spam box and junk folders

      Reply
  58. Denice says

    October 16, 2015 at 7:21 pm

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

    Reply
    • Leah4sci says

      October 31, 2015 at 6:28 pm

      haha thanks Denice. The solutions are linked at the end of the quiz

      Reply
  59. Amina Farha says

    October 16, 2015 at 10:28 am

    thanks
    your help it means a lot to me

    Reply
    • Leah4sci says

      October 25, 2015 at 1:53 am

      You’re very welcome Amina

      Reply

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