Question

AT&T O D Jul 13% 18:43 PM Х HW 4.pdf Using the HNMR spectrum and molecular formula for the product, determine the structure. Complete the synthesis using an organometallic reagent and an aldehyde or ketone (Full: correct synthesis and HNMR assignment, partial correct NMR assignments) CHO Reagents for Synthesis 5 4 3 2 1 PPM 4.2 ppm, 1H, s 3.2 ppm, 1H,1 1.92 ppm, 2H, m 0.98 ppm, 12H, d 2. Using the HNMR data and molecular formulas, determine the reactant and the product. (Full: Both reactant and product are correct with NMR assignment, partial reactant or product with correct NMR assignment) 1 1. | .| CLO 2.13 ppm, GH, CH 5.00 ppm, 1H, S 1.80 ppm, 3H, s 1.16 ppm, 6H, s 3. Draw the mechanism for the previous 2 reactions. Remember arrows should go from nucleophile to electrophile (Full both mechanisms correct with no more than 1 minor error, partial: one mechanism correct with no more than 1 minor error OR both correct with no more than 3 minor errors) 4. Draw the product of the following reaction. (Full: correct product, partial: correct connectivity but functional group error) 5. Draw the intermediates and final product for the following synthesis (Full: all products correct with no more than 1 minor error, partial: 3 out of 4 correct with no more than 1 minor error) Mg. Eto 1.co, 2.H, H2O SOCI NH O

Answer 1

The first question given is actually wrong, and the product's m.f will be C7H16O and not C7H14O, which is depicted according to the given nmr details, the mechanism of the first two reactions are given in the following picture, and nmr predictions also,

Br 1 OH "Cea Hibos" and not C₂H 40 Reagent for Synthesis : d 1. mg, THE 2. d H d Н.) H н CH3 + c 3. 0 H Н. a a = 4.2 ppm ,11,5 b = = 3.2 ppm, 1H,t c = 1.92 ppm, 2H, m d = 0.98 8 ppm, 12H, d. C

. 애 2 . 대3 CH3 병 2. H, H20 상 cho" с 3 쓰 CC) 50098m A1.. 르 6H, singlet and S= 2.13ppm 71 19 (M) 6H,S "Pentant? S : 1.16ppm Reactant" CH 0 product 3개, s, S 1-30ppm

3. Mechanen for a : Mg Br Br Mg, THE (1) Sy (+) mgbr Ooh omg Br СН3 Сн, Н х 3 с не сня CH₂ си, 13 - Mg Brolt ой с. не с. . 댕 с неб Mechanism for 2: (10) го т сн. C3 С Но 1, H₂O of C
The fourth reaction is the condensation reaction, the products of the reaction will be given as follows,

O 4. 8옷 -N I
The intermediates and the final products of the fifth question is given as follows, it contains grignard, carboxylation, chlorination, and amination occurs.

Mg. - 5. ang Be Br | Etzo U02 .ل 2. H1,H20 . 애 نازان socz N Hz cl با هم مالهما 00: