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Problem Conversions Solutions

1 Howcouldyoucovertbutanoicacidintothefollowingcompounds?Morethanonestepmaybe
required.
(a)Butan1ol


(b)1bromobutane


(c)pentanoicacid


(d)but1ene


2 Howcouldyouconverteachofthefollowingcompoundsintobutanoicacid?Morethanonestep
mayberequired.
(a)Butan1ol


(b)1bromobutane


(c)but1ene


(d)1bromopropane


3 Predicttheproductofthereactionofpmethylbenzoicacidwitheachofthefollowing:
(a)CH3MgBrinether,thenH3O+


+
(b)KMnO4,H3O


+
(c)LiAlH4,thenH3O


4 Identifythemissingreagentsaeinthefollowingscheme:
a b c
OH Br CO2H

d e
OH O

+
(a)H ,H2O
(b)PBr3
(c)Mg(0),ether,thenCO2
(d)LiAlH4
(e)DessMartinperiodinane

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