6 4 ptscomplete the following reaction and write the

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(6) (4 pts).Complete the following reaction and write the IUPAC name for the product. IUPAC name: BONUS QUESTION (7) (Bonus, 5 pts) The reaction of diethyl ether with hydrogen bromide (a strong acid) gives as a main product bromoethane. Write the detailed mechanism for this reaction. F 3 C S O O Cl + CH 3 CH 2 OH ? CH 3 OH
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CHM-1320 April 2001 page 9 of 15 Last name or student number: ..................................... (8) (7 pts) The reaction of 2-methylpropane with chlorine gives the products and yields indicated below. (a) (4 pts) Write a complete mechanism for the formation of the major product (B, formed in 63% yield) and identify the individual steps. (b) (2 pts) In no more than 50 words explain why the main product is the one involving breakage of the stronger C-H bond. Note: Primary C-H ~ 98 kcal/mol Tertiary C-H ~ 91 kcal/mol (c) (1 pt) Write the correct IUPAC names for both products. H 3 C C H CH 3 CH 3 Cl 2 , light H 3 C C CH 3 CH 3 H 3 C C H CH 2 Cl CH 3 + Cl A: 37% yield B: 63% yield
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CHM-1320 April 2001 page 10 of 15 Last name or student number: ..................................... (9) (6 pts) Each of the following reactions shows some products. For each product indicate if it is correct or incorrect and add the structure of any missing organic product. Missing main products can be totally different from those given, isomers or enantiomers. Either no product is missing, or only one is missing in each reaction (that is, do not write more than one missing product!). You can simply cross out clearly any incorrect product. If no statement is made about one of the products, markers will assume that your answer is that it is a correct product . Example: (a) (b) (c) CH 3 Br CH 3 OH CH 3 OH CH 3 CH 2 OH Br CH 3 Question Answer CH 3 Br CH 3 OH CH 3 OH CH 3 CH 2 OH Br CH 3 OH CH 3 CH 3 missing CH 3 1) BH 3 2) H 2 O 2 /HO CH 3 H CH 3 OH H OH H H H 3 C CH 3 1) MnO 4 , HO , heat 2) H + CH 3 CH 2 COOH CH 2 H 3 C H 3 C HBr H 3 C CH 3 Br CH 3 H CH 3 CH 2 Br CH 3
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CHM-1320 April 2001 page 11 of 15 Last name or student number: ..................................... (10) (10 pts including 4 bonus for part b) (a) Using Grignard chemistry show how you could convert acetone into 2- methyl-2-butanol. Introduce any reagents that may be needed. (b) (4 Bonus points) Using a combination of nucleophilic substitution and Grignard chemistry convert the product of part (a) into 2,2-dimethylbutanoic acid. Show clearly all reagents needed. Suggestion: Do this at the end. Do not waste valuable time on these bonus points unless you have a good idea of how to do it.
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