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CHM 1321 Supplemental Exam - Organic Chemistry, Study notes of Chemical Processes

Bryn Athyn College of the New ChurchChemical Processes

A supplemental exam for CHM 1321 Organic Chemistry class. The exam consists of 26 questions, each with a specific number of points. The questions cover various topics such as predicting products, drawing mechanisms, determining formal charges, and drawing structures. Students are required to read instructions carefully and follow regulations during the exam. The document does not include answers.

What you will learn

  • What is the expected major product for the following reaction sequence? Specify whether enantiomers may be formed.
  • a) b) answers.
  • Which alkyne would produce the products below upon ozonolysis?
  • Draw the major product of the reaction below
  • Determine the formal charges on each atom except hydrogen.
  • Draw the Fischer projection of the following compound

Typology: Study notes

2021/2022

Uploaded on 09/12/2022

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Supplemental Exam – CHM 1321 – B Prof. Sandro Gambarotta
Date: July 2019 Length: 3 hours
Last Name: _______________________ First Name:__________________
Student #_______________ Seat #
Instructions:
- Calculator permitted (Faculty approved or non-programmable)
- Closed book
- Molecular model allowed
- Periodic Table allowed
Read carefully:
Cellular'phones,' unauthorized' electronic' devices'or'course'notes'(unless'an'
open-book'exam)'are'not'allowed'during'this'exam.''Phones'and'devices'must'
be'turned'off'and'put'away'in'your'bag.''Do'not'keep'them'in'your'possession,'
such' as' in' your' pockets.' ' If' caught' with' such' a' device' or' document,' the'
following' may' occur:' ' academic' fraud' allegations' will' be' filed' which' may'
result'in'your'obtaining'a'0'(zero)'for'the'exam.'
By signing below, you acknowledge that you have read and ensured that you are
complying with the above statement.
Signature:________________________________
"
"
Please"put"your"INITIALS"IN"THE"BOX"when"you"have"verified"that"there"are"11"pages"
in"this"exam."
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Download CHM 1321 Supplemental Exam - Organic Chemistry and more Study notes Chemical Processes in PDF only on Docsity!

Supplemental Exam – CHM 1321 – B Prof. Sandro Gambarotta Date: July 2019 Length: 3 hours Last Name: _______________________ First Name: __________________ Student # _______________ Seat # Instructions:

  • Calculator permitted (Faculty approved or non-programmable)
  • Closed book
  • Molecular model allowed
  • Periodic Table allowed Read carefully: Cellular phones, unauthorized electronic devices or course notes (unless an open-book exam) are not allowed during this exam. Phones and devices must be turned off and put away in your bag. Do not keep them in your possession, such as in your pockets. If caught with such a device or document, the following may occur: academic fraud allegations will be filed which may result in your obtaining a 0 (zero) for the exam. By signing below, you acknowledge that you have read and ensured that you are complying with the above statement. Signature:________________________________ Please put your INITIALS IN THE BOX when you have verified that there are 11 pages in this exam.

question 11 ../2 22. ../ 2 1 ../ 4 12 ../ 4 23 ../ 2 2 ../1 13 ../ 3 24 ../ 5 3 ../ 3 14 ../ 2 25 ../ 3 4 ../ 4 15 ../ 2 26 ../ 5 ../ 1 16 ../ 3 6 ../ 1 17 ../

  1. ../1 18 ../
  2. ../ 2 19 ../
  3. ../ 2 20 ../ 2
  4. ../1 21 ../ 3 Total ../ 61 Total. ../ 1. ( 4 point) Predict the product for the following reaction and draw the complete mechanism. Answ: see slideshow for mechanism 2. (1 point) Which of the following is the weakest acid? Ans: IV

5. (1 point) Determine the formal charges on each atom except hydrogen. Ans: 6. (1 point) Which of the following is a correct resonance structure for compound A? Ans: IV 7. (1 point) What is the IUPAC name of the following compound? Answ. 4-ethyl-3,6-dimethyloctane 8. (2 points) Draw a Newman projection for the following compound as viewed down the indicated bond and in the conformation shown. C S C N H H H C S C N H H H

  • 1 0 - 1 0 N^ NH^ NH NH N A I II III (^) IV

Answ

9. (2 points) Draw the most stable chair conformation of the following cyclohexane Answ 10. (1 point) Are the two substituents cis or trans? Answ. trans 11. (2 points) What is the relationship of the following two structures? Answ. Diastereomers 12. ( 4 points) Draw the meso isomer of the following compound. O (^) O HO OH HO O (^) O HO OH HO

15. (2 points) Draw the expected major product(s) of the following reaction: Answ. . 16. (3 points) Draw the major product of the reaction below Ans: 17. (2 points) What is the expected major product for the following reaction? Answ. 18. (2 points) What is the expected major product for the following reaction sequence? HBr ? Br

  1. Hg(OAc) 2 , H 2 O
  2. NaBH 4 , NaOH
  • enantiomer OH

Answ 19. (1 point) Identify the expected major organic product resulting from the following reaction sequence. Answ 20. (2 points) What is the expected major product of the reaction sequence shown below? A) I B) II C) III D) IV E) V Ans: A 21. (3 points) Which alkyne would produce the products below upon ozonolysis?

  1. BH 3 • THF
  2. H 2 O 2 , NaOH
  • enantiomer OH CH 3 1.^ O^3
  1. Zn/H 2 O ? H 3 C O H 3 C O H O H O CH^3 H O H O H O OH O CH 3 O O I II III IV V

24. (5 points) a) b) answ.

25. (3 points) Predict the product formed when cyclopentanone is treated according to the sequence below. Write the mechanism answ.

26. (3 points) Predict the major product for the following reaction. Answ: