Microsoft Word - CHEM212MechansismsAssignment.docx CHEM212/BCHM212 Assignment for Introduction to Organic Reaction Mechanisms Prof. A. J. Fairbanks Important information This assignment will...

Hi, I needed help with my Chemistry assignment, it is organic chemistry.


Microsoft Word - CHEM212MechansismsAssignment.docx CHEM212/BCHM212 Assignment for Introduction to Organic Reaction Mechanisms Prof. A. J. Fairbanks Important information This assignment will contribute 10% to your overall mark for the CHEM212/BCHM212 course. The deadline for handing in your work is 5pm Friday of Week 7 (25th May). Written work, which should be clearly marked with your name and the course code and have a completed assignment cover-sheet attached, must be handed in to the slots outside the Chemistry general Office (room 532) on Level 5 of West (formerly the Rutherford Building). Late work WILL NOT be accepted for marking. Be aware of the University rules on plagiarism/copying - you must do the assignment on your own. For this assignment copied and/or plagiarized work will initiate academic disciplinary action. Note that it is very easy to spot copied errors in reaction mechanisms. ANSWER ALL FIVE QUESTIONS 1) The following chemical reaction actually gives a mixture of three products. Predict the structure of the three compounds that are formed, and provide mechanisms for their formation, classifying them as appropriate (e.g. as SN1, SN2, E1, E2 or other ...). [6] 2) Predict, with reasoning, the major alkene product that is formed in each of the following elimination reactions. Draw a curly arrow mechanism to explain your answer. [3 x 4] Br EtOH heat + Product 1 Product 2 C9H16O Product 3 C9H16O + C7H10 Ph Ph Me Br ButOK (i) (ii) Ph OMe NO2 NaOMe MeOH benzene Ph S Ph O heat(iii) 3) Give mechanisms for the following synthetic transformations, and explain why the molecule drawn is the major reaction product. [3 x 4] 4) The following type of SN2 reaction is not a good way to make amines. a) Draw the structures of other products that would be formed in this case, and explain why their formation cannot be stopped. [3] b) Suggest an alternative two-step method for converting 1-bromopropane into propylamine. [2] 5) Give a mechanism for the following reaction. Explain why this reaction pathway, rather than any alternative processes, is followed. [5] Total Mark / 40 NaOH aq.Cl HMe OH Me Me single enantiomer (i) single enantiomer OH HMe OH Me Me Br O NMe2 Br 2 equivalents NaNH2 NH3(l) (ii) (iii) (i) MeI (ii) NaOH O Br NH3 K2CO3 H2N 1-bromopropane propylamine HO Me Me OH H+ OMe Me