Question

6. (Bpts) For each example below, draw a structure that is consistent with the formula and H NMR spectrum provided. In some cases, additional IR spectral information is provided. Assign each peak to the appropriate hydrogen atoms in the structure by using the labeling convention discussed in class

Any work or explanation would be much appreciated. Thank you!

Answer 1

a) Cg Hro 02 : Jegree unsaturation 20 10 2 means there mud h -5. bengen g 441 67cm ndicades - oup Conjugated uil Analysis of H NMR , 69 There no any exchangeable peaka. So, J thore ho -oH gou Thus he Aruune is is(onj'ugafrof wi ph ing 2-6 , 3H This carbanypo HG (Hз0) 7 3-8 (3,3h) 7-,24) 63(d, 2) 6 C5 HIO02 - Degree ounsaturahion= 12-(0 means a doulle bond

14 Cm rdicales here mus e an ester beccuse hormek haY mas -gous hare 1700 Analysis « A NMR 2.2 (4) 3.6 S:3. ptm () -0-CH3 -8 ppm 6Ppmsenta and 2-2) indicales H 6(extetj / 0-8(A, 3H) 2.A) Thus can e given as s1ruclurre 16 (Bexfef, 2H A) CH2 CH3 (8) T 2.2, 2 A) T 0-1,3H) 36(A, 3 H)

CHIO 02 t5omen ocamourd ohfained in (6) Degae unaturation 2-0 2 double = I means hond group Analysis oH NMR sextel 5- 1-7 ( * ) 21 (8 ), 40-4-1() 0-9 4.0-41 (4)15- 1. (scafet) and o-9 Indicales -o- CH2-CH2-Ct3 Thus dutiore (an be given y 40-4 , 2) CH2 Н 1 15-1(Aeutet, 3H) 2/3, 3 H)