Search for question
Question

Test 5 - ORG II (Lecture 5 - ORGII / Module 5 - ORGII): 5 points 1. Please predict the products for each of the following reactions using benzophenone. (2 points = 0.1 points each reaction x 20): Hint: 8, 10, 14, 16 (Grignard); 9, 19 (Wittig); 12 (hydrazone then Wolf-Kishner); 15 (Baeyer- Villiger); 20 (Corey-Chaykovsky); 6, 17 (reduction); 4 (imine); 5, 11 (enamine); 1, 7 (ketal); 2 (thioketal); 13 (oxime); 18 (hydrazone); 3 (thioketal then reduction) Me2S- SCH₂ Ph3P-CH2 NH,NH, [H+], Dean-Stark NaBH4 HOCH2CH2OH [H+], Dean-Stark 19 20 20 1 HSCH2CH2CH2SH له 2 [H+] 1. HSCH2CH2SH, [H*]¸ 3 4 2. H2, Raney Ni CH36 MeOH 18 1. MgBr 17 2. H₂O 16 МСРВА 15 14 1. i-PrMgBr 13 12 11 10 7 CH3NH2 [H+], Dean-Stark (CH3)2NH [H+], Dean-Stark 1. LiAlH4 2. H₂O CH3OH [H+], Dean-Stark 2. H₂O 1. CH3MgBr NH [H+], Dean-Stark 2. H₂O NH₂OH [H+], Dean-Stark 1. NH2NH2, H3O* 2. КОН-Н2О 150°C 1. PhMgCl 2. H₂O PPh3 COOEt 1 2. Name each chemical reaction below (Grignard Reaction; Friedel-Crafts Acylation; Baeyer-Villiger Reaction; Wittig Reaction; Corey- Chaykovsky Epoxidation; Clemmensen or Wolf-Kishner Reduction): (1 point): (a) (0.2 points) DOI: 10.1021/acs.orglett.5b02851 from https://www.organic-chemistry.org/ EDG EDG HFIP, r.t., 2 h n: 1, 2, 3 Answer: (b) (0.2 points) DOI: 10.1021/ol050337b Me .OMe 2 M Ph P=CH₂R': Ph.P=CH R' N HCI OMe R 'N' .R' 2.1 eq. Buli (2.5 M in hex.) .R' + THF Me -78°C r.t., 20 h 2.2 eq. Br Ph₂P-CH₂R' THF, -15°C, 30 min Answer: (c) (0.2 points) DOI: 10.1002/1521-3773(20020315)41:6<1057::AID-ANIE1057>3.0.CO;2-H R 1.3 eq. PhMgCl + (2 M in THF) 1.3 eq. (-)sparteine toluene, -78°C, 24 h 0 R Ph OH Answer: (d) (0.2 points) DOI: 10.5012/jkcs.2002.46.5.479 R H 0.1 eq. BF3⚫OEt₂ 1 eq. MCPBA benzene, r.t., 1-3h R' R" R OH "R" n: 0,1 Answer: (e) (0.2 points) DOI: 10.1021/j00479260 0.2 eq. S + 2 eq. BnBr Ar Answer: 0.2 eq. BuчNHS04 2 eq. NaOH, r.t., 1-2 d MeCN/H₂O (9:1) Ar Ph Ar Ph 2 3. Complete synthetic transformations (0.2 each reaction x 10 = 2 points): H3CO Na2Cr2O7, H2SO4, H2O H-N→ OH CrO3Cl Ph3P conditions? + Me2S-CH2 PCC MgBr 1. 2. H₂O [H+] Dean-Stark Hint: cyclohexyl migration rate is similar to t-Bu (3° alkyl) 1) LiAlH 4 (excess) 2) H₂O BONUS Na2Cr2O7, H2SO4, H2O CI 3 -0 H 4. BONUS QUESTION: Propose chemical structure for C10H12O (1 point): FTIR: TRANSMITTANCEI%! LOD D 4000 3000 1H NMR: Hint: Sextet at 1.8 ppm. 2000 1500 1000 500 HAVENUMBERI -11 11 10 9 8 7 6 5 4 3 HSP-01-476 ppm N 1 4 13C NMR: Hint: 4 aromatic 13C signals (140 - 120 ppm) 200 180 160 140 120 100 80 CDS-04-618 ppm Answer: 60 60 40 20 SDBSWeb: https://sdbs.db.aist.go.jp (National Institute of Advanced Industrial Science and Technology, 1/22/2022)