Question

Identify the appropriate reagents from the table to accomplish steps a-h. Select the reagents in the order that they are to be used; i.e. 382 means that step 'a' is PCC, step 'b' is NaNH2, and step 'c' is Br2, H2O.

CH2CH2Br CH2CH2Br Reagents 1. CH3)3CO 2. Bro, H20 3. PCC 4. Mg, ether 5. HaO 6. PPh 7. Br2, CH2Cl 8. NaNH CH CH2 CH CH2 OH CHCH2Br CCH2Br CECH

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Answer #1

The reagents are a = 1 , b = 2 , c= 3 , d= 1 , e = 7, f= 8, g = 8 and h = 5

a is used for eleimination to give alkene thus is t- butoxide

b used for addition of HObr, thus Br2/H2O

C used tooxidise OH to ketone, so it is PCC

d is again elimination by t- butoxide

f is elimination of two HBr to give alkyne , hence 2 equivalents of NaNH2

g is to get alkynide ion by using one equivalent of NaNH2

h is reaction of alkynide with a ketone followed by acidification to give a tertiary alcohol, thus h is H3O+

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