TheIodoformReaction TheIodoformReaction

Iodoform Iodoform Tri Tri iodomethane iodomethane iodomethane CHI 3

CCEAMODULE2 CCEAMODULE2
2.6.11 2.6.11

Prepareiodoformandknowitsuseto distinguishbetweenalcohols containingCH CH(OH)andother 3 alcoholswithspecificreferenceto recrystallisationandmeltingpoints. recrystallisationandmeltingpoints.

IodoformReaction IodoformReaction
Thereactionoccursonlywithalcohols

containingthegroup. CH CH(R)OH CH(R)OH 3 Worksforallsecondaryalcoholsand Worksforallsecondaryalcoholsand ethanol. ethanol. Orcarbonylcompoundscontainingthe Orcarbonylcompoundscontainingthe CH CO CO group group 2

IodoformasaTestforSecondary Alcohols Alcohols

Addasolutionof Addasolutionofiodineinpotassiumiodidetoan iodineinpotassiumiodidetoan

appropriateamountofalcohol. appropriateamountofalcohol. Followed Followedbysodiumhydroxide bysodiumhydroxidesolutionand bysodiumhydroxide solutionand sodiumhypochloritesolution. sodium hypochloritesolution. hypochloritesolution.
AlcoholswiththegroupCH CH(R)OH 3

willformayellowprecipitatewithanantiseptic smelloftri smelloftri iodomethaneCHI iodomethaneCHI . 3 Theprecipitateisfilteredundersuction. Theprecipitateisfilteredundersuction.

 Carbonylcompoundswiththegroup

CH CH CO(e.g.propanoneCH COCH 2 3 3 usedin thepracticalinthevideo)willalsoforma yellowprecipitatewithanantisepticsmellof tri tri iodomethaneCHI iodomethaneCHI . 3 Theprecipitateisfilteredundersuction. Theprecipitateisfilteredundersuction.

SuctionFiltration
Setupthefilterpump(forsuctionfiltration)andcollecttheyellowcrystals. Setupthefilterpump(forsuctionfiltration)andcollecttheyellowcrystals.

NB:thatsuctionfiltrationisusedbecauseitisquicker thatsuctionfiltrationisusedbecauseitisquicker

SuctionFiltration SuctionFiltration

Dissolve the crude product in a minimum amount of hot solvent to form a hot saturatedsolution saturated solution. . Let the hot saturated solution cool slowly slowly. . Crystalswill Crystals willform form. . Filter off the crystals using suction filtrationin filtration ina aBuchner Buchner funnel. Buchnerfunnel Buchner .

Recrystallisation PurificationofaSolid P urificationofaSolid

Dryinginadessicator Dryinginadessicator

Allowthecrystalstodryinadessicator Allowthecrystalstodryinadessicator

Recordingthemass Recordingthemass
RecordthemassofthecollectedIodoform

crystalsandusetheequationbelowtowork outthepercentageyield. outthepercentageyield.

Percentageyield= Percentageyield=actualmass actualmassx100 actualmass x100

theoreticalmass Referringtopracticalandtheoretical considerations,whyisthe%yieldnot considerations,whyisthe%yieldnot 100%?

WhyisthePercentageYield not100%? not100%?

Practical:

Lossduringtransfer Lossduringfiltrationand recrystallisation recrystallisation Theoretical Theoretical Sidereactions Reactionmaynotgoto completion. completion.

TestingPurity TestingPurity
The melting point of a solid is a good

guide to its purity and may be used for identifyingthe identifying thesolid solid. . Usually a pure substance substance will melt over a a o range of 1 C i. .e e. . it has a sharp melting point. point . Pure Iodoform has a sharp melting melting o pointat point at119 119 C. C .

TakingMeltingPoint TakingMeltingPoint
Ameltingpoint Amelting pointtube tubeis is sealedat issealed is atone oneend end. . The substance is crushed with the sealed endof end ofa amelting melting point pointtube point tubeon ona afilter filterpaper paper orwith or witha apestle pestlein ina aclean clean mortar. cleanmortar clean . The crushed solid is placed to a depth of about2 about 2cm cmin ina amelting meltingpoint melting pointtube tubeclosed closedat at oneend one end. .

The tubeis Thetube isthen thenplaced placedin placed inthe themelting meltingpoint point apparatusand apparatus andheated heated. heated. heated The temperature is recorded when the crystalscollapse crystals collapseto toa a a clear clearliquid liquid. . A pure solid gives gives a a SHARP MELTING POINT. POINT . Impurities Impuritieslower lowerthe themelting the meltingpoint point. .

Testingthemeltingpoint Testingthemeltingpoint