8487-Q-02B-KEY - Friday, January 21, 2011 Please PRINT Last...

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Friday, January 21, 2011 CHM 2211-8487 Quiz #02 Form B Page 1 of 1 Please Last PRINT name: First name: UFID: ______ /20 pts. Put your answers in the spaces, or check R or insert your answer Graded by Caroline 1. ( 6 pts ) See problem 16.19 (a) and (c) Suggest two combinations of aldehydes and Grignard reagents that might be used to prepare the same 2° alcohol – after work-up as detailed in (b). (b) For work-up, provide suitable reagents that convert the first-formed alkoxide (not to be shown) into the final product, the 2° alcohol as shown. O PhCH 2 H (a) Grignard reagent Et 2 O H HO CH 2 Ph CH 2 CH 3 CH 3 CH 2 MgBr O CH 3 CH 2 H (b) Work-up reagents H 2 O HCl (c) Grignard reagent Et 2 O PhCH 2 MgBr Work-up reagents are the same as in (b) (a) Aldehyde (c) Aldehyde _____ 2. ( 8 pts ) See problems 16.23, 16.24 . Show how a Wittig reaction can bring about the conversion of acetaldehyde into ( E )-2-butene. (a) Draw the structure of the bromoalkane that reacts with triphenylphosphine to form the corresponding (b) phosphonium salt ; draw the structure (recall: salts come with
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