CHEM 372-Problem Set 13 - Ester and amide hydrolysis 4. Esters undergo hydrolysis to the corresponding alcohol and carboxylate: ethyl acetate is hydrolyzed to ethanol and acetate. However, amides are surprisingly stable under strong base. Draw the first intermediate in the hydrolysis of the amide. Is a good leaving group present? Continue with the mechanism and prove to yourself that the basic hydrolysis of an amide is more difficult than ester hydrolysis. NaOH H3C CH3 H3C OH Na CH3 heat H3C NH CH3 NaOH heat

A synthesis of the anti-tumor agent tamoxifen is shown below. In the following questions, you will fill in the missing reagents and structures for this synthesis. First, you can try starting with the given starting material then synthesizing tamoxifen using any reagents you wish. Then, you can go back and complete the multiple choice questions. of Synthesis of A tamoxifen OH Step 1 H tamoxifen Step 1A B Step 2A Mg Step 2 Step 4 A Step 3 НО 1) A 2) H3O+

In the following reactions substituent X was varied between electron donating and electron withdrawing. If you use the usual o values, do you expect a positive or negative p value for each equilibrium? Should each reaction be more sensitive or less sensitive to the X substituent than benzoic acid? Explain your reasoning for each answer. NaOEt H X HOET

Draw the structure of the major product formed by the reaction below: امله 2 NH, The mechanism for the following reaction occurs in a stepwise fashion. еля Draw the correct mechanism in the space below. Be sure to add lone pairs and charges to structures as needed. е H,C Draw the structure of the major organic product for the following reaction. OH CH,OH H.SO

The reaction scheme below, proposed by students, will not work. Why not? HO -Br OH Mg HO -MgBr ether 1. cyclohexanone 2. mild H3O+ HO O The Grignard reagent will immediately react with the phenolic OH group, destroying the Grignard reagent before it can react with cyclohexanone. O The H30+ in the second step will destroy the erignard Reagent. O The H3O+ in the second step needs to be strong acid, because the Grignard reagent is a strong base. O Cyclohexanone is too sterically congested.

I need 4 and 3 please

Payalben

Can you explain the mechanism? Can you provide a shortcut?

Please provide a mechanism for these simple reactions below!

Can you help me get the major products of the following reaction please