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CHEM 205 Worksheet (WS4) (64 points total)
Copyright protected – Do Not Post to third-party websites (Chegg, Course Hero, or similar website
– will result in zero on assignment and “F” for the course).
Key Topics: Configurational isomers, Chirality, Absolute Configuration, Isomer Relationships
1. (16pts) Determine if each compound below is optically active or optically inactive. Include
drawings/illustrations that justify each choice.
2. (18pts) (a) Draw bond-line structures and include appropriate wedge and dash notation for the following
compounds. (b) Identify each pair that would be optically inactive as a 50/50 mixture. (c) Identify pair of
compounds that represent diastereomers.
3. (i) (6pts) Draw an arrow pointing to each carbon that is considered a stereocenter in the structures below.
There will be a 1pt per occurrence deduction for each carbon that is mislabeled as a stereocenter.
(ii) (12pts) Label the absolute configuration at each carbon stereocenter as either (R) or (S).
Copyright ©, 2023, Doane OLA, All rights reserved.
4. (12pts) A research study published in The Journal of Biological Chemistry (2020) and mentioned in
Science Daily (2020) discusses a drug that has been used in the treatment of SARS and MERS type
coronaviruses. Recent clinical trials were conducted by the NIH at the University of Nebraska Medical
Center (UNMC), which is about 80 miles northeast of Doane University, to test for its effectiveness towards
combating the novel coronavirus COVID-19. Refer to the articles posted in module 4 and other resources
you have at your disposal to answer the following questions.
Answer each part below accordingly:
(a) (1pt) What is the name of the drug discussed? _________________________________________
(b) (i) (1pt) Look up (ie. google) and draw the structure of this drug. (ii) (1pt) How many carbon atoms in
this structure are considered chiral?
(c) (i) (1pt) What is the configuration of the chiral carbon which is not part of a ring? Circle the correct
label (R or S) below. (ii) Using the structure drawn above, label the priorities according to Cahn-Ingold-
Prelog rules. (1pt)
R or S
(d) (i) (1pt) How many additional stereoisomers does this compound have? (Note, the phosphorous in
this structure is also a stereocenter). (ii) (2pts) Propose a reason why the stereochemistry of this drug is
important.
(e) (2pt) What biochemical enzyme has this drug been shown to inhibit and why is this important?
(f) (2pt) Draw the structure and provide a name of the RNA nucleotide that this drug most closely resembles
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