18. Draw the structures of Compound 18a. and 18b. (18 pts), clearly indicate your assignments of...

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18. Draw the structures of Compound 18a. and 18b. (18 pts), clearly indicate your assignments of all proton resonances (8 pts

30 200 Unsat. Index = (2C+2-H-X+Ny2 = e = 2.00 ppm, 25 20 f = 1.27 ppm, 4.90 singlet, 2H 720 Compound 18a: C,H,O, triplet, 3H

Characteristic IR Stretching Frequencies 요 C-OR in cm1 (1150-1300) =0 broad N-H O-H (3000-3500) 3000 CEN (2200-2400) 2000 RC-

(4.6-5.0) O -H RCHCN RNCH O CH CCH ROH (25-3.3) (2.1-2.6) (0.8-1.7) =CHR COH (10-13) CH (9.1-10) FCH (4.2-4.8) (6.0-9.5) (5.2

-N:CEN KMnO, H,SO Fe, HCI KMnO,, NaOH, H2O, cold 00 (CH3),COCOCOC(CH), Ag(NH3)2, H,0 KMnO, NaOH, H,0, heat AICI LiAIH LiHAI(0

O NK H2SO4,SO, CH,COOH CH,ONa CISO,OH PPhy SOCI 1-BuOK, heat Zn(Hg), HCI Zn, H0 HAI(i-Bu), (DIBAL) HCN, NaCN HNO, HNO, H,SO H

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