Question

7. (8 pts) A student carried out the following reaction sequence. Given the data below. provide structures for compounds A through D. Do this neatly by drawing the structures in the appropriate box below. 1) KMnO,/NaOH + 1) SOCI, D) DIBAL- H D 2) 1, 0 2 ) CH,OH2 ) H0 Compound A has 8 carbons and Compound D was found to be C&H,O, by mass spectrometry and had the following spectral data: 'H NMR: 9.87 ppm 8 (IH, s), 7.82 ppm 8 (2H, d), 7.01 ppm 8 (2H, d), 3.83 ppm 0 (3H, s); "C NMR: 191, 165, 132, 130, 115, 56 ppm 8; IR: 3061, 2990, 2792, 2702, 1707, 1599 cm. Compound B Compound A Compound D Compound C

Answer 1

[Answer 2 2 Compound D fH NMR data miF - Compound D = 484802 DU= 2C+2-H = 218 )+2-8-5 2 Compound D have 5-degree of unsaturation. This indicate Compound 0 have benzenering in its structure. a) Inmrdata 9.87 ppm (141, ) 7- H 7-82 ppm ( 24, d), para disubshtested benzenety 7oolppm ( 26, d) I present. 3.83 ppm ( 34, 5) 3 -OCHy gooup. b) IBC NMR data 1912pmg - H. 165 ppm a sp²c (=d) 132 ppm =) sp²c (=(-) 130ppm = sp²c(=(-1) 115 ppm = sp²c (=CH) S6 epm = -ост, 15990 g (=c in benzine oing es IR data 3061cm -c-4 2990 cm =(-4 2792 cm, 270 2 cm ( 1707 cm

on the basis of Compound D is IH NMR 13C NMR R, the structere ok ha OYH< OTH T H - 9.87(s) 7.82ld] Tool(d) H ock - 3.83(s) # e by by DIBAL-H reduction - Thi DIBAL-H reduction. This indicate acis ester. Esler con seduchoo coith DIBACH to The acyl chloride prepared boom D is obtained from Corpound c is ester: Estero gives aldehyde. D. # The esker E is obtamed som Quyl chloride and roethanol Chlooide prepared soom cachosuyllic acid B com reachoo with socle. They compound B is neid. The Bis obtained by kmnou ceidahen ols A methyl benzime dewatnes which om csudahom coith Kmnare gives B - Structure of A, B, C&D com km nou cridahen ols A. This A is ayol to Imhou Ingoy SoCl2 DIBALŲ 4 2. tho 2' reall . 2. tho ocus