Alcohols, Phenols and Ethers

Alcohols, Phenols and Ethers

Department of Chemical Engineering, University of the Philippines, Diliman, Quezon City  Date Performed: February 27, 2015 Date Submitted: March 4, 2015

Answers to Questions

1.) Gie the ba!a"ce# ba!a"ce# e$uatio"# for for a!! the reactio"#. reactio"#. %. &u &uca ca# # 'e#t e#t (tha"o!  *+!, "+! 2 +*-+*2*  *+! / "o reactio" #oroy! a!coho!  *+!, "+! 2 +*-)2+**  *+! / +*-)2+*+!  *2  'ert3buta"o!  'ert3buta"o!  *+!, "+!2 +*-)-+*  *+! / +*-)-++!  *2 e"y! a!coho!  *+!, "+! 2 +6*5+*2*  *+! / "o reactio" . idat idatio" io" of %!coho %!coho!# !# (tha"o!  8M" 4 +*-+*2*  8M"4 / +*-+*  *2  M"2  8  #oroy! a!coho!  8M" 4 2 +*-)2+**  8M"4 / 2 +*-)2+  2 *2  M"2  8   'ert3buta"o!  'ert3buta"o!  8M"4 +*-)-+*  8M"4 / "o reactio" e"y! a!coho!  8M" 4 +6*5+*2*  8M"4 / +6*5+*  2 *2  M"2  8  Diethy! ether  8M"4 +6*5+*2*  8M"4 / "o reactio" +. 9eactio eactio" " of of Phe" Phe"o!# o!# Phe"o!  r 2 +6*5 *  -  r2 / +6*5*r-  - * *rr r r i" orth ortho o a"d ar ara o#itio"#) Phe"o!  8M"4 +6*5*  8M"4 / +6*42  *2  M"2  8  oye" i" ara o#itio") Phe"o!  Fe+! 6 +6*5*  Fe+!- / ;Fe+6*5)6<-3  - *+! = > "ahtho!  Fe+! - +6*5?-  Fe+!- / Fe+ 6*5?-)-  - *+! •

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?itrohe"o!  Fe+! - r+6*5*  Fe+!- / Fer+6*5)-  - *+! romohe"o!  Fe+! - +10*7*  Fe+!- / Fe+10*7)-  - *+!

2.) (!ai" @hy the &uca# te#t i# a!icab!e o"!y to a!coho!# co"tai"i" 5 or !e## carbo"#. t i# o"!y a!icab!e to a!coho!# @ith 5 or !e## carbo"# for the#e comou"d# are #o!ub!e i" the &uca#A reae"t becau#e of their abi!ity to form *3bo"d#. +omou"d# @ith more tha" 5 carbo"# are too !are to be #o!ub!e i" the reae"t a"d therefore @i!! "ot react @ith it. -.) (!ai" @hy tertiary a!coho!# a"d ether# ca""ot u"dero oidatio" uo" reactio" @ith ota##ium erma"a"ate. B"der #tro" reactio" co"ditio"# #uch a# #tro" oidii" ae"t# 8M"4) a"d e!eated temerature#, c!eaae of +3+ bo"d# taCe# !ace a"d a miture of carboy!ic acid# co"tai"i" !e##er "umber of carbo"# i# formed. 4.) +orre!ate the #tructure of the he"o!ic comou"d# @ith the mea#ured * a!ue#.  'he hydroy! rou i" he"o! i# direct!y attached to the # 2 hybridied carbo" of be"e"e ri" @hich act a# a" e!ectro" @ithdra@i" rou. Due to thi#, the chare di#tributio" i" he"o! mo!ecu!e, a# deicted i" it# re#o"a"ce #tructure#, cau#e# the oye" of the hydroy! rou to be o#itie.  'he re#e"ce of e!ectro" @ithdra@i" rou# #uch a# "itro rou# e"ha"ce# the acidic #tre"th of he"o!. 'he eect i# more ro"ou"ced @he" #uch a rou i# re#e"t i" ortho a"d ara o#itio"# due to de!oca!iatio" of  the "eatie chare i" he"oide io". 9efere"ce# 1. +arey F%. 2010. Organic Chemistry 8 th ed. McGra@ *i!!. ?e@ EorC. 2. McMurry, (. 2007. Organic Chemistry  th ed. rooC#3+o!e, ?e@ EorC.