Question

2. Draw the structure of the major organic product that is formed from the following reaction. Draw this structure in the box at the bottom of the next page. Then use letters to label all the sets of chemically equivalent carbons in this structure. The broadband proton-decoupled 13C NMR spectrum of the product is shown below. DEPT 90 and DEPT 135 data are included in the table on the following page. Use this spectroscopic data to make clear assignments of all the resonances and determine the identity of the product. t, use the curved-arrow notation to draw the mechanism by which the product is formed. Show all lone pairs, nonzero formal charges, countercharges, and reversibility or irreversibility. Analyze this mechanism to predict whether or not the product is optically active. Then suggest a diastereomer that theoretically could Next been formed. Finally, refer to the mechanism to explain in detail why the reaction forms the observed product with complete diastereoselectivity See bttp:/lwww.csun.cdu-hechm007./333 comc.pdí for a l3C NMR correlation table. CHy CH212 H,C CH Zn/Cu 13.0 30.8 25.7 23.5 14.7 11.6 9.1 47.1 S0 45 40 3530 25 20 1 105 PPM

Answer 1

This is a simmon smith reaction, where alkenes reacted with CH₂X₂ in the presence of Cu and Zn. in the first step Zn reacted with CH₂ present in CH₂Cl₂ form a intermediate product then cyclopropane was formed.

In DEPT spectra ,

DEPT 90 gives signal for CH group, DEPT 135 gives signal for CH, CH₃ as positive peak and for CH₂gives negative peak. Hence from the given DEPT data there is three type of CH₂ present, two type of CH₃ present and three type of CH present. So the final product cyclo propane was mentioned above. Here stereochemistry plays the important role, the reactant was trans isomer so attack must be done on the same side where the substituents was present. so final product also trans.