Week 6-Case Study

pdf

School

Rutgers University *

*We aren’t endorsed by this school

Course

123

Subject

Chemistry

Date

Jan 9, 2024

Type

pdf

Pages

3

Uploaded by ChefStar7503

Report
Week 6 Case Study: Chemical Structure of Neurotransmitters Acetylcholine is a neurotransmitter of the autonomic nervous system which sends information through the neurons to target organs. by 1. (1 pt) Identify the circled functional group. HC v H,! _12 '\‘ —N—C—C -, 3 Functional group: Ealec Ha(:'SC/ H, .. CHs 2. (1 pt) Calculate the formal charge on the nitrogen of this structure. Show your work. ik \ ¢ o0 bonds -~ corced eeChans 5= x| 3. (5 pt) Draw the Newman projections for the different conformations obtained through 60° bond rotations around the CH2-CH2 bond of this molecule. Abbreviate the two functional groups as -OAc and -NMes. Me;N o Goudine HG Ac ' Ho A NMes ACH1 g 0 IH H \ 4 H H H H 4. (1 pt) Identify which conformation(s) are gauche (circle): 1 @ @ @ 5 5. (1 pt) Identify which conformation is anti (circle one): 1 . 4 @ 6. (1 pt) Identify which conformation(s) are eclipsed (circle): 1 @ @ @ 5 7. (1 pt) Identify the most stable conformation(circle one): 1 2 3 4 @ /11 pt
Acetylcholine has several possible conformations. Scientists wanted to know which conformation bound to the receptor at the synapse. So, they synthesized the two molecules shown below. 8. (2 pt) Convert these two compounds to Newman Projections: Isomer 1 Isomer 2 9. (1 pt) Which of the conformatlons of acetylcholme matches the structure of Isomer 1? (circleone): 1/ 2 Jie B8 e # . /&‘flc) pasd! €l (2 b0 10. (1 pt) Which of the conformations of acetylcholine match‘és the structure of Isomer 2? (circle one): @ 2 5 4 5 [ Onc \@"’3" fiee eleipLo w4 The scientists then tested to see which of these compounds would react with the receptor in the synapse producing a cholinomimetic response: Isomer 1 had about the same activity as acetylcholine Isomer 2 had about no appreciable activity. 11. (1 pt) Which conformation of acetylcholine is most likely to bind to the receptor (The isomer that binds the receptor will be the conformation that most resembles the isomer with the most activity.) Asv B «pesents (circle one): 1 2 QQY“ A eg\\ps-e, DB ) . ¢
The scientists tried the same experiment with another set of compounds. 12. (4 pt) For each of these four structures above, convert the wedge-and-dash structure to the chair structure by adding the acetyl (-OAc) and the trimethylammonium group (- NMes) to the right positions. NMes A “OAc NMes Oi):o sanacs Isomer B i Ofc_ | somer C OAc OAC / {NMej Nive3 (:O o Isomer D "OAc GAc 13. (2 pt) What is the relationship between Isomer A and Isomer B? Ditstereomavs (LR(ES) 14. (2 pt) What is the relationship between Isomer A and Isomer C? (0—;‘73 £S ‘53 ' \ ® 3 Olocer isomos DU- nok Su(erimpaale MOV g gox Isomer A had the most activity of these four structures. S T T Va7 15.(1 ?t) Which conformation of acetylcholine most resembles Isomer A? This will indicate which conformation of acetylcholine is most likely to bind to the receptor. 153 (circle one): 1 2 3 4 @ g 2 | \* N My 3 /9 pt | 6} AO
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
  • Access to all documents
  • Unlimited textbook solutions
  • 24/7 expert homework help