CHEM333 Exam1 review and practice(1)

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University of South Carolina *

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333

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Chemistry

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Dec 6, 2023

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Uploaded by JudgeLightning1063

9/7/2021 1 CHEM333 Fall 2021 Exam 1 September 14, 2021 during lecture On paper. 75 minutes. Exam ends at end of lecture. Don’t be late. No notes. Work alone. You may use your model kit. No sharing of model kits. There are more than 50 practice problems in this document. Pace yourself; be sure you can answer each question in 2-3 minutes. No, there won’t be 50 questions on the exam. Use the objectives for chapter 1-3 (and general chemistry prerequisite list) on the course syllabus as a checklist while you study. Use these practice questions to help in your preparation for the exam. This is NOT a “practice exam.” Do not memorize these questions as the questions on your exam will be different. Disclaimer There are an infinite number of combinations and questions about the ways the concepts in organic chemistry are related. These pages are not intended to be a definitive or closed list of exam questions; they are presented as a sample of the level of critical thinking combined with memorization needed to succeed on the course assessments. Consider this compound to answer this set of short answer questions 1. Number of hydrogens _____ 2. Formula _______________ 3. Number of sigma (σ) bonds _____ 4. Number of pi (π) bonds _____ 5. Number of lone pairs of electrons _____ 6. Add any formal charges 7. How many carbon atoms are sp 3 hybridized? ___ 8. Which other atoms are sp 3 hybridized? ___ 9. How many carbon atoms are sp 2 hybridized? ___ 10. What other atoms are sp 2 hybridized? ___ 11. Draw a bond to H to show a proton with p K a about 45. H 2 N O Answer these questions about the indicated structure 12. How many carbons? _____ 13. How many hydrogens? _____ 14. How many lone pairs of electrons? _____ 15. How many sp 2 carbons? _____ sp 3 carbons? _____ sp carbons? _____ Answer these questions about the indicated structure 16. Indicate the hybridization of every atom. 17. Draw on the lone pairs of electrons. 18. How many total hydrogens? _____ 19. How many total σ (sigma) bonds? _____ 20. How many total (π) pi bonds? _____

9/7/2021 2 21. Draw valid resonance structures (and the hybrid resonance structure) for this compound. O 22. Choose the invalid resonance structure. 23. Assuming all the C, N, and O atoms have a full octet, add all lone pairs of electrons and formal charges to creatine (shown). O O N NH 2 H 2 N 24. Which atoms in the molecule shown are sp 3 hybridized?

9/7/2021 3 25. Draw the structure of isooctane, the definition of 100 octane in gasoline, which can be written as (CH 3 ) 3 CCH 2 CH(CH 3 ) 2 26. Circle and label all functional groups in the structure of aspartame. 27. Circle the compound(s) which contain(s) an amine functional group? 28. How many total atoms are connected to the indicated carbon atom? 29. How many lone pairs of electrons are on the indicated carbon atom? 30. What is the hybridization of the indicated carbon atom?

9/7/2021 4 31. In the following structure, all of the nonbonding electrons are shown, but the formal charges (F.C.) are missing: Which is true of this molecular representation? A. An atom with a F.C. of 0 is closest to the viewer B. An atom with a F.C. of +1 is closest to the viewer C. An atom with a F.C. of –1 is closest to the viewer D. An atom with a F.C. of –2 is closest to the viewer E. None of these 32. Circle the compounds that have +1 as a formal charge on the nitrogen atom. 33. How many lone pairs of electrons are on the oxygen atom? 34. In the progesterone molecule shown, how many hydrogens are cis to the two methyl groups?

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