O,SCH, cis and trans H3C 2. excess NH, NH,CI NH2 a = Proton transfer d= Radical chain addition g= E2 Elimination h = Syl Nucleophilic substitution i = Sx2 Nucleophilic substitution b=Lewis acid base e = Electrophilic addition f=El Elimination c= Radical chain substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. Submit Answer Try Another Version 1 item attempt remaining 1.

Which of the following (A or B) is the major product of the reaction below. Explain your answer in terms of the reaction mechanism. + HBr A Br B

3) Fill in the red box(es) with the missing reactant(s), reagent(s), product(s), solvent, and/or conditions and write a reasonable mechanism for the reaction. Not every box needs to be used and not every box necessarily corresponds to only a single species. If no reaction occurs OR no reagents exist to perform the reaction state, “NOT POSSIBLE” AND explain why. HO OH dil. H₂SO4

The reaction between isocyanide 1 and ketone 2 occurs only after a base (t-BuOK) is added to a solution of the reactants in ethanol and CH2Cl2. The final product is nitrile 4, which is believed to arise from ethanolysis of intermediate 3 under the reaction conditions. Draw a plausible reaction mechanism to describe the formation of 4 from 1 and 2. Draw all intermediates and show all electron-pushing. You are not expected to know if your proposed mechanism is the actual mechanism supported by experimental evidence, but it must be reasonable, and the electron pushing should be correct. Hint: start by deprotonating 1 and forming the first bond, then label and map the atoms onto the intermediate. Ts Ts = ONS=O N=C= t-BuO K H -- EtOH, CH2Cl2 2 3 NEC

It has been observed that the reaction of B to produce Product D proceeds 10,000X faster than the reaction of A to produce Product C. Provide a brief explanation for the difference in observed rates.

Name the product of reaction with mechanism also.

The epoxide shown below can form two different products depending on which reaction condition is used. What are the products of each of these reactions? BRIEFLY explain why you get different products depending on the reaction conditions. By far, the easiest way to do this is to show the mechanism for the key step in each reaction and clearly explain this step. HCH₂CH3 CH3 D н’ CH3OH