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Download BONUS 2 Organic chem 1 (Chem-40010) University of California (San Diego), Roman A Valiulin and more Exams Organic Chemistry in PDF only on Docsity!
| Portia) Question 1 UC (SanDiego) Organic chemistry 1 Exam help Course code-40010 solved Bonus Please name the following compounds. Make sure you spell each name correctly, leave no spaces since any variations in spelling will result in the loss of points. Example t: (12,3€,62)- 1,6,8,8-tetramethylcyclonona-1,3,6-triene Example. 2)-1,6,8,8-tetramethylcyclonon- 1-en-3-yne an | Structure 1 Cyclodecan-1,6-diyr 2 Structure 2. (12)-cyclodec-1-en- Structure 3. (1Z.6Z)-cyclodeca-1 a. Structure 4 (1E,6Z)-cyclodeca-1 0.3 / 0.5 pts UU 5. fe} Structure § (2EAZ72,9E)-6,6-d Answer 1: cyclodecan-1,4-diyne Answer 2: (1Z)-cyclodec-1-en-6-yne Correct! Answer 3: (1Z,6Z)-cyclodeca-1,6-diene Correct!” | Answer 4: (1E,62Z)-cyclodeca-1,6-diene Answer 5: (2E,4Z,7Z,9E)-6,6-dimethylcyclodeca-2,4,7,9-tetraen-1-one Question 2 0.1/0.1 pts ICS} CamScanner Question 3 Br. Br Br 1. Predict the correct product for this reaction. 0.1/0.1 pts 2. Choose ALL correct representations of the product using Newman projection. Br. H Br H Br. H Br H a | Question 4 0.1/0.1 pts ICS} CamScanner | Correct Question 5 | 0.1 / 0.1 pts Choose the correct representation of the structure using chair conformation. | Question 6 0.1/0.1 pts | H hye iM H All) B H a Cc dy ‘a Oo cl | (1 Ne roy H Ht Sy | i 4 H 7 . H A pn ae ce f\ 7+ Compound 1; humulone (a-lupulic acid) OH O Ho” 3a So ia Red center: S Green bond: neither Compound 2: Red center: | neither Compound 3: andrographolide Ho” HO Top Green bond: E | Bottom Green bond: neither Compound 4: Please determine the stereochemistry using the hint below and name this compound. Hint: Use the link and check Rule 5 and Fig. 18: hitp:/ursula.chemyale.edu/~ clem220/chem220}s/STUDYAIDS/Isomers/CIP%20rul Red center: neither Name: (26,5Z)-hepta-2.5-d | | Compound 5: sucrosé HO. Red center 1: § Red center 2: § Answer 1: Correct! Answer ?- Answer 9: Ss Correct! feartial Question 8 Please predict the outcome of each E2 elimination reaction: Hint: Assume it can only occur if the beta-hydrogen atom is anti-periplanar to the leaving group. Type you answer as a letter: A, B. ...., or F. Problem 1: Answer to Problem 1: © Hoe: ; CHs anti- ” ers ““c, —-E2 elimination Q CH; u u ou 0.5 / 0.6 pts CH; CH; Problem 2: Answer to Problem 2: © CH anti. o tine “cl E2 elimination a A B Cc CHs CH E F CHs aCHy Problem 5: Answer to Problem 5: 8 H3G Sr H. “a oD CH CH; H CH; CH; H CH3 bp” CH; anti- o eet E2 elimination a B CH; : D CH; E CH; H CH3 bY + CH; Dg CH3 Cc CH; H CH3 bY F CH; H CH; + CHy DA LCHs CH; CHs ne ep hor Problem 6: Answer to Problem 6: © H3C. s Mca Tae Hy Hs anti. bY E2 elimination ? A B CH; CH, H One D, ¢ »CHs D E CH; CH H CH3 Hy CH3 D*| bY + + CH; CH; H nyt oa. CH, H D CH; CH3 CH; CH; CH 0.1/0.4 pt: Question 9 Please predict the outcome of each reaction below: Type you answer as a letter: A, B, ...., or F. Problem 1: https://doi.org/10.1024 /ol101705j = Answer to Problem 1: © Hint 1. Assume the reaction can ONLY occur at the MOST ELECTRON RICH double bond. | Hint 2. Assume the reaction can ONLY occur from the least sterically hindered side of the molecule. Draw or build a 3-dimentional conformation to support your answer. | -———J | equivalent ) { m-CPBA a | Problem 2: https://doi.org/10.1016/S0040-4039(00)76159-4 B Answer to Problem 2:| © Hint. Assume the reaction can ONLY occur from the least sterically hindered side of the molecule. Draw or build a 3-dimentional conformation to support your answer. eee | on | 2D | ac HO" HO" Problem 3: https:/doi.org/10.1021/ja9093988 & Answer to Problem 3: © Hint. Assume the reaction can ONLY occur from the least sterically hindered side of the molecule. Draw or build a 3-dimentional conformation to support your answer. ICS} CamScanner 
