21.96 A student treated methyl 2-methylpropanoate with sodium methoxide dissolved in methanol. After the solution was refluxed for 2 hours, the mixture was analyzed by NMR, IR, and mass spectrometry. Those spectra are shown below. (a) Draw the mechanism of the reaction the student was expecting and draw the expected product. (b) What do the spectra suggest occurred? (c) Explain these results. 100- 80- 60 40- 20 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 4000 3500 3000 2500 2000 1500 1000 500 Chemical shift (ppm) Wavenumbers (cm-1) 100 80 60 40 20 0+ 10 20 30 40 50 60 70 80 90 100 110 120 mlz Relative intensity % Transmittance

+ hv H.2 + Propose a mechanism for the reaction that fully accounts for the formation of both products.

Predict the nucleophilic substitution product.

5) Provide the products necessary to complete the synthesis below. Indicate what mechanism was used for each product. OH PB13 Но heat

GIVE A COMPLETE MECHANISM FOR THE FOLLOWING REACTION

3. What product would you get from the reaction between 2,4-dimethyl benzaldehyde with propylamine in the presence of H+? Establish the reaction and propose a reaction mechanism

Predict the product of the following reactions

Subject: chemistry

Predict the product(s) of the following reactions, including stereochemistry when necessary and identify the mechanism of each substitution reaction (SN1 vs SN2). Draw the reaction mechanism (reaction arrows) for any one of the reactions to show how the product is formed.

What would be a proposed mechanism to get from cyclohexanol to cis-2-methoxycyclohexanol?  I know how to get from cyclohexanol to trans-2-methoxycyclohexanol would be to go through acid-catalyzed dehydration via H2SO4, then epoxide ring formation via mCPBA and then alcohol-catalyzed opening, but don't know how to do for the cis version, if possible.