Experiment 8 - Organohalides

Classification Tests for Organic Halides

Arnau, C. L., Capunitan, V. N., Cerezo, O. U. , Claudio, E. C., Co, M. A., Cortes, M. V. 2D-PH, Group 2, Department of Pharma!, "ault! of Pharma!, #ni$ersit! of %anto &omas Espa'a (oule$ard, )*)+ Manila, Philippines

Abstract rani halides are orani ompounds in hih one or more h!droen atoms ha$e /een su/stituted /! a haloen atom. Most of these ompounds are s!ntheti and flame retardant. 0n this e1periment, e1periment, different different tests ere made to differenti differentiate ate primar! primar!,, seondar! seondar!,, and tertiar! tertiar! orani halides /ased on their %N ati$it! and to mae a distintion /eteen their %N) and %N2 mehanisms. %ample ompounds of n-/ut!l hloride, se-/ut!l hloride, tert-/ut!l hloride and hloro/en3ene ere su/4eted throuh the (eilstein test, %N) 5eati$it! &est 6aloholi AN78 and %N2 5eati$it! &est 6Na0 in aetone8. All ompound samples produed a positi$e result ith (eilstein test /! impartin a ree flame, affirmin the presene of hlorine. 0n %N) 5eati$it! test the ompounds ere made to reat ith 29 ethanoli AN7 to o/ser$e %N) 5eati$it!, all samples produed a hite preipitate ith $ar!in times of formation here tert-/ut!l hloride e1hi/ited the fastest and n-/ut!l hloride as the sloest. Chloro/en3ene as o/ser$ed to e1hi/it no reation in the %N) 5eati$it! test. :hile in the %N2 reati$it! test usin Na0 in Aetone as the reaent, it as o/ser$ed that all ha$e samples e1hi/ited the formation of a hite preipitate e1ept for hloro/en3ene; hloro/en3ene; hereas hereas n-/ut!l n-/ut!l hloride hloride e1hi/ited the fastest fastest time of formation formation and tert-/ut!l hloride as the sloest.

Introduction In the labor laborator atory y and in indust industry ry,, alkyl halides are used as solvents for relatively non-polar compounds, and they are used as the starting materials for the synthesis of many compou pounds. Alkyl halides are are classied as primary (1o), seco second ndar ary y (o), or tertiary (! o) according to the number of carbon atoms directly bon bonded to the carbon bearing halogen. "omp "ompou ound nds s in #hic #hich h a halo haloge gen n atom is bonded to a sp-hybridi$ed carbon are called vinylic halides or phenyl phenyl halide halides. s. %inyl %inylic ic halide halide is a general term that refers to a

comp compou ound nd in #hic #hich h a halo haloge gen n is attached to a carbon atom that is also forming a doub ouble bond to another carbon atom. &henyl halides are compounds in #hich a halogen is attached to a ben$ene ring ring.. &h &hen enyl yl hali halide des s belo belong ng to a larger larger group group of compoun compounds ds called called aryl aryl halide halides. s. 'ogethe ogetherr #ith #ith alkyl alkyl halides, these compounds comprise a larger group of   compounds kno#n simply as organi organic c halide halides s or organo organohal haloge ogen n compounds. 1 *rganic halides are organic compoun compounds ds contai containin ning g a haloge halogen n atom atom bond bonded ed to a carb carbon on atom atom..

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 'he said halogen atom can either be chlori chlorine, ne, +uorin +uorine, e, bromi bromine, ne, or iodine. 'hese compounds are are consid consider ered ed to be +ame +ame retar retardan dantt and and most most of them them are are sy synt nthe heti tic. c.  'he halogen atom of an alkyl halide is attached to a sp!-hybridi$ed carbon. 'he arrangement of groups around the carbon atom, therefore, is gener generall ally y tetrah tetrahedr edral. al. ecause ecause halogen atoms are more electr electrone onegat gative ive than than carbon carbon,, the carb arbon-halogen bond of alkyl halides is polari$ed. alogen atom si$e increases as #e go do#n the peri period odic ic tabl table e #her #herea eas s +uor +uorin ine e Methodology

Samples &he samples used in the e1periment e1periment ere n /ut!l hloride,  sec-/ut!l  sec-/ut!l hloride, tert -/ut!l -/ut!l hloride and hloro/en3ene.  Reagents &he reaents used in the e1periment ere 29 ethan ethanol oli i AN N7 and )+9 Na0 in anh!drous aetone.  Beilstein Test: Test: Copper Halide Test  Test  &he test as onduted /! preparin one opper ire for eah sample to /e used. n one end of eah opper ire a small loop as made. &he loop as then heated diretl! in the the o1id o1idi3i i3in n 3one 3one of a non-l non-lum umin inous ous flame enerated /! a (unsen /urner. 0t as ontin ontinuou uousl! sl! heated heated until until the reen reen olor  olor 

atoms are the smallest and iodine atoms atoms the larges largest. t. "onse "onseuen uently tly,, the the carb carbon on-h -hal alog ogen en bond bond leng length th increases and carbon-halogen bond strength decreases as #e go do#n the periodic table.   'he ob/ectives of this e0periment e0periment are are (1) (1) to di2e di2errenti entiate ate prim primar ary, y, seco second ndar ary, y, and and tert tertia iary ry orga organi nic c halides based on their 34 reactivity, () () and to di2e di2errenti entiat ate e bet# bet#ee een n 341 an d 34 as reactive mechanisms #ith organic halides.

until the o1ide adhered to the loop. &he loop as as then then then then ool ooled ed sli sliht htl! l! and and as as dipped into the li?

A primar! iodo ompound produes a preipitate