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E test Module 10 Organic chem 1(Chem-40010) University of California (San Diego), Exams of Organic Chemistry

Its a solved past E test of Module 10, fall 2024, University of California (San Diego) Organic chemistry 1 (Chem-40010) Instructor: Roman A. Valiulin

Typology: Exams

2023/2024

Available from 05/26/2025

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Question 1 Please predict the product tor each of the following reactions, Make sure to clearly Indicate the correct stereochemistry for each compound: w A oe c D 2, not "tug 7, OH oo Seen oe Ou A Correct! OH OEt be} CamScanner i Question 2 Please predict the product for each of the following reactions, Make sure to Clearly indicate the correct stereochemistry for each compound: Correct Answer is D: be} CamScanner ‘Question 4 be} CamScanner Question 5 i Please predict the product for each of the following reactions, Make sure to clearly indicate the correct stereochemistry for each compound: i \ | / ~~ - a ll. y ra ' A B be} CamScanner Question 7 Please predict. the product for each of the following reactions. Make sure to clearly indicate the correct stereochemistry for each compound: | | A 8B c D a 4 Br HO, 40H i of im ety oe one “A ak ca erly y be} CamScanner Question 8 Please predict the product for each of the following reactions. Make sure to clearly indicate the correct stereochemistry for each compound: be} CamScanner Question 10 Please predict the product for each of the following reactions, Make sure to clearly indicate the correct stereochemistry for each compound: be} CamScanner Question 11 if Propose best Williamson ether syntheses for the following compounds, Select all applicable options (multiple answers can be possible). Note: Some compounds cannot be made using Williamson synthesis reaction. ay, KH | Br 2 A: ~ OH bee “ Se ' = ’ ') Sy2 KH ; aa is B: Cyn oo eo— ‘OH 1 OK Syi €: Cannot be synthesized using Wiltiamson ether syntheses. DA Correct! KH 2@ © -on Se es ‘OK be} CamScanner i> Question 13 i Propose best Williamson ether syntheses for the following compounds. Select all applicable options (multiple answers can be possible). Note: Some compounds cannot be made using Williamson synthesis reaction. oD A: on a a abs a oe Opn 2 Os | C: Cannot be synthesized using Williamson ether syntheses. Correct Answer is C: Cannot be synthesized using Williamson ether syntheses. Question 14 Propose best Williamson ether syntheses for the following compounds. Select all applicable options (multiple answers can be possible). Note: Some compounds cannot be made using Williamson synthesis reaction. oS i KH e@ A: Lon COANE AIAN wa Lok — Sy2 Br FE NaH ee. Con ey se Su2 C: Cannot be synthesized using Williamson ether syntheses. Br NaH e@ crease ‘ONa —_! Te! Sy2 a Question 16 Predict the expected product for each reaction and provide IUPAC) name for the correct starting material to yield the desired epoxide: ‘4 i | mCPBA Q 4.NaSH NAME SAMIR UT | 2.H20 boa id A B c SH OH OH ME Box 1 (name); 2-¢thyl-1-butene Box 2: 8 | Answer 1: 2-ethyl-1-butene Answer 2; B | | Correct Answer: 2-ethyibutene 2-ethylbut-1-ene 2-ethyl-1-butene 3-methylenepentane bey 4. NaSH ies _mCPB. | —— ee ? D SH i be} CamScanner Question 17 Predict the expected product for each reaction and provide IUPAC name for the correct reagent used to yield the desired epoxide: A B c D a Br 2 Br : OH s OH Br OH OH Br Box 1 (name): 3 chloroperoxybeni Box 2: D Answer 1: 3-chloroperoxybenzoic acid Answer 2: mCPBA Oo HBr OH o- poral AS ae ta, m-CPBA 3-chloroperbenzoic acid meta-chloroperbenzoic acid m-chloroperbenzoic acid 3-chloroperoxybenzoic acid meta-chloroperoxybenzoic acid m-chloroperoxybenzoic acid e- oe be} CamScanner Question 19 Predict the expected product for each reaction and provide IUPAC name for the correct starting material to yield the desired epo» OH 0,90 paciiaieh cotneees 2 EtOH | D cl fe} H,S0, NAME _ ~ Tees A B c Eto, «, ,OH +, ,OEt HO, WOK BOT HOD Bro Xk Box 1 (name): 2"methyl-1-butene Box 2: © | it (ie pa Answer 1: f | Fit . 2-methyl-1-butene Hh | Answer 2: | if whl rail il | Correct Answer: a Ong? ,OEt be} CamScanner Question 20 Predict the expected product for each reaction and provide IUPAC name for the correct starting material to yield the desired epoxide: Posse feaitererbrna 14 | [2 | MCPBA ° 1, CH3CH,MgBr | NAME _—->+ A, — | | | “2.420 | 5 A B c D a a Gow aa ~S~on OH 6H i Box 1 (name): Propene Box 2: A Answer 1: propene Answer 2: A \ Correct Answer: =/ mores | A 1 Chee Haeaee 2 HO prop-t-ene Propene 1-propene