8. What products would be formed from the reaction of isobutyl bromide, (CH3)2CHCH2Br, with each of the following reagents? a. NaOH b. NaOCH3 c. NaCN d. KOt-Bu/tBuOH e. NaOAc (NaOOCCH3) HCCH-CH2-A H3
Solution
(a)
(CH 3 ) 2 CHCH 2 Br + NaOH --------> (CH 3 ) 2 CHCH 2 OH + NaBr
(b)
(CH 3 ) 2 CHCH 2 Br +NaOCH3 ---------> (CH 3 ) 2 CHCH 2 OCH 3 + NaBr
(c)
(CH 3 ) 2 CHCH 2 Br + NaCN --------> (CH 3 ) 2 CHCH 2 CN + NaBr
(d)
(CH 3 ) 2 CHCH 2 Br --- KOt-Bu / tBuOH --------> (CH 3 ) 2 C=CH 2
(e)
(CH 3 ) 2 CHCH 2 Br --- NaOAc -----> (CH 3 ) 2 C=CH 2
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