Alcohols and Phenols

(1)

O O H H R R H H O O H H .. . . .. Hydrogen bonding Hydrogen bonding CH CH₂₂ OHOH CH CH₃₃ CHCH₃₃ CCH H OOHH C C OHOH CH CH₃₃ CH CH₃₃ CH CH₃₃ CH CH₃₃ ethanol ethanol (primary) (primary) 2-propanol 2-propanol (secondary) (secondary) 2-methyl-2-propanol 2-methyl-2-propanol (tertiary) (tertiary)

ALCOHOLS & PHENOLS

An important portion of this corse is the reco!nition of or!anic chemistry fnctional !rops" An important portion of this corse is the reco!nition of or!anic chemistry fnctional !rops" #hese are parts

#hese are parts of a molecle$ %itof a molecle$ %ith a specific strcth a specific strctre that fnctions re that fnctions in a certain %ay" in a certain %ay" Not onlyNot only are yo to learn to reco!nie the fnctional !rops (a listin! can 'e fond in yor tet'oo or on are yo to learn to reco!nie the fnctional !rops (a listin! can 'e fond in yor tet'oo or on the 'ac co*er of this la'oratory manal)$ 't yo are also to learn the physical and chemical the 'ac co*er of this la'oratory manal)$ 't yo are also to learn the physical and chemical properties

properties of of each each of of the the fnctional fnctional !rops !rops stdied stdied in in the the corse" corse" #his #his la'oratory la'oratory eercise eercise %ill%ill introdce yo to t%o of these fnctional !rops$ alcohols and phenols$ as %ell as some of their introdce yo to t%o of these fnctional !rops$ alcohols and phenols$ as %ell as some of their physical and chemical properties"

physical and chemical properties"

Alcohols Alcohols

Altho!h yo may 'e familiar %ith +alcohol, as a 'e*era!e$ the %ord actally represents an Altho!h yo may 'e familiar %ith +alcohol, as a 'e*era!e$ the %ord actally represents an entir

entire classife classificatication of or!anic molion of or!anic molecles and not secles and not st one s'stat one s'stance" nce" AlcohoAlcohols contails contain then the

−

OH (hydroyl) fnctiOH (hydroyl) fnctional !rop attached to onal !rop attached to a satrated car'on" a satrated car'on" Notice that %e Notice that %e diddid not not call this call this

the hydroide ion$ 'ecase this !rop does

the hydroide ion$ 'ecase this !rop does not not act as an ionic s'stance" act as an ionic s'stance"

Alcohols are classified into three cate!ories. primary (/0)$ secondary (20) and tertiary (10)" #his Alcohols are classified into three cate!ories. primary (/0)$ secondary (20) and tertiary (10)" #his cla

classissificficatiation on is is 'as'ased ed on on the the nmnm'er 'er of of carcar'on-'on-contcontainainin! in! !ro!rops ps ( (

−

for an alyl or an for an alyl or an

aromatic !rop) attached to the car'on 'earin! the hydroyl !rop" 3f the car'on 'earin! the aromatic !rop) attached to the car'on 'earin! the hydroyl !rop" 3f the car'on 'earin! the

−

OH has one  OH has one 

−

!rop$ the molecle is a primary alcohol" 3f t%o  !rop$ the molecle is a primary alcohol" 3f t%o 

−

!rops are attached$ it is a !rops are attached$ it is a

secondary alcohol" 3f three 

−

!rops are attached$ the alcohol !rops are attached$ the alcohol is tertiary"is tertiary"

3"

3" PhyPhysisicacal Prol Propepertrtieies of Als of Alcohcohololss #he hydro

#he hydroyl !rop presenyl !rop present t in all in all alcalcoholohols s is a is a polpolarar fn

fnctictional !roonal !rop" p" #he pol#he polariarity of this !roty of this !rop allo%p allo%ss alcoho

alcohols to form hydrls to form hydro!en 'onds" o!en 'onds" SmalSmall chain alcoholl chain alcoholss are a'le to mi %ith %ater 'ecase of the hydro!en are a'le to mi %ith %ater 'ecase of the hydro!en 'ondin!

'ondin! interactions interactions that that %ill %ill occr occr 'et%een 'et%een thethe hydroyl fnctional

hydroyl fnctional !rop and the !rop and the %ater" %ater" 3f the 3f the -!rop-!rop of the alcohol 'ecomes too lar!e ho%e*er$ the sol'ility of the alcohol 'ecomes too lar!e ho%e*er$ the sol'ility of the alcohol %ill decrease"

(2)

4nCl 4nCl₂₂

Procedure: Procedure:

/"

/" PlaPlace ce /5 drops of /5 drops of eaceach h alcalcohoohol l (et(ethanhanol$ /-'tol$ /-'tanolanol$ $ 2-'2-'tatanolnol$ $ 2-m2-methethylyl-2-p-2-propropanolanol and /-octanol) into

and /-octanol) into its o%n its o%n test t'e" test t'e" Add /-2 mAdd /-2 ml of %ater l of %ater to each t'e" to each t'e" ecord yorecord yor o'ser*ations on the data sheet"

o'ser*ations on the data sheet" 2"

2" Place aPlace another nother /5 dr/5 drops of ops of each of each of the a'the a'o*e alo*e alcohols cohols into into its oits o%n te%n test t'st t'e" e" Add /-Add /-22 ml of dichl

ml of dichloromethane" oromethane" ecord yor o'ser*ations ecord yor o'ser*ations on the data son the data sheet"heet"

66

66CACA7#7#3O3ON6N666 8383CHCHLOLOOO9E9E#H#HANANE 3S E 3S :L:LA9A99A9A;L;LE" <EE" <EEP EP ALALL L :L:LA9A9ESES A=A>"

A=A>" A?O38 ;EA#A?O38 ;EA#H3N@ :79ES" H3N@ :79ES" =O< =O< 3N #HE 3N #HE HOO8 ASHOO8 AS 97CH AS POSS3;LE

97CH AS POSS3;LE" " =EA SA:E#> @LA=EA SA:E#> @LASSES 3N #HESSES 3N #HE LA;OA#O> A# ALL #39ES6

LA;OA#O> A# ALL #39ES6

33"

33" ChemChemicaical Propl Properterties of Alies of Alcohocoholsls

#he classification of an alcohol as primary$ secondary or tertiary (see a'o*e) affects the chemical #he classification of an alcohol as primary$ secondary or tertiary (see a'o*e) affects the chemical properties

properties of of the the alcohols" alcohols" #his #his difference difference in in chemical chemical properties properties can can 'e 'e sed sed as as a a means means ofof ide

identintificficatiation" on" #he Lcas tes#he Lcas test t and the chromand the chromic acid test are ic acid test are t%o commt%o common methodon methods s sesed d toto distin!ish amon! primary$ secondary and tertiary alcohols"

distin!ish amon! primary$ secondary and tertiary alcohols" A"

A" LLcacas #s #esest.t.

#he Lcas rea!ent contains inc chloride and hydrochloric acid" =hen the Lcas rea!ent is #he Lcas rea!ent contains inc chloride and hydrochloric acid" =hen the Lcas rea!ent is allo%ed to react %ith an alcohol$ an alyl halide is formed" #his alyl halide %ill not 'e allo%ed to react %ith an alcohol$ an alyl halide is formed" #his alyl halide %ill not 'e sol'le in %ater$ ths clodiness or a second layer of droplets %ill form if the test is positi*e" sol'le in %ater$ ths clodiness or a second layer of droplets %ill form if the test is positi*e" =ith this rea!ent$ tertiary alcohols react immediately$ secondary alcohols in 1 to /5 mintes$ =ith this rea!ent$ tertiary alcohols react immediately$ secondary alcohols in 1 to /5 mintes$ and primary alcohols may tae an hor or lon!er$ or may ne*er react"

and primary alcohols may tae an hor or lon!er$ or may ne*er react"

-OH  HCl -OH  HCl -Cl  H-Cl  H22OO (insol'le) (insol'le) Procedure: Procedure: 1"

1" Place 2 mPlace 2 mL of the LL of the Lcas reacas rea!ent in a t!ent in a test test t'e" Add B dr'e" Add B drops of eops of ethanolthanol" Shae t" Shae the t'ehe t'e to mi the materials and note the time reired for the mitre to 'ecome clody or to to mi the materials and note the time reired for the mitre to 'ecome clody or to separate into t%o layers" ecord yor o'ser*ations" epeat this procedre for separate into t%o layers" ecord yor o'ser*ations" epeat this procedre for /- 'tanol$ 2-'tanol$ and 2-methyl-2-propanol"

(3)

  C C OOHH O O   C C   O O C C     OH OH   66

66CACA7#7#3O3ON6N666 HyHydrdrochochloloriric c acacid id is is *e*ery ry cocorrrrososi*i*e" e" AnAny y spspilill l shsholold d 'e 'e imimmemedidiatatelelyy flshed %ith %ater"

flshed %ith %ater" =ear safety !lasses =ear safety !lasses in the la'oratory at all in the la'oratory at all times"times"

;"

;" ChChroromimic Acc Acid id #e#estst..

Chromic acid (acidified dichromate$ an oidiin! a!ent) can also 'e sed to distin!ish Chromic acid (acidified dichromate$ an oidiin! a!ent) can also 'e sed to distin!ish 'et%een

'et%een types types of of alcohols alcohols 'y 'y oidiin! oidiin! the the alcohol" alcohol" Primary Primary alcohols alcohols are are oidied oidied toto car'oylic acidsD secondary alcohols are oidied to etonesD and tertiary alcohols are not car'oylic acidsD secondary alcohols are oidied to etonesD and tertiary alcohols are not oidi

oidied" ed" 8rin8rin! the oidation$ the oran!e-! the oidation$ the oran!e-red color of the chromic acid chan!es to a 'le-red color of the chromic acid chan!es to a 'le-!reen soltion"

!reen soltion"



 HH22CrOCrOBB     Cr Cr 22(SO(SOBB))11   HH22OO (pr

(primaimaryry) ) (re(red-od-oranran!e) !e) (car'o(car'oyylic lic aciacid) d) ('l('le-e-!re!reen)en)



 HH22CrOCrOBB     Cr Cr 22(SO(SOBB))11   HH22OO (

(sseeccoonnddaarryy) ) ((rreedd--oorraann!!ee)) ((eettoonnee) ) ((''llee--!!rreeeenn))



 HH22CrOCrOBB   No No eactioneaction

(tertiary) (tertiary)

B"

B" PlPlace /5 droace /5 drops of aceps of acetotone in a ne in a tetest tst t'e'e" Add F " Add F drdropops of ethas of ethanonol and 2 l and 2 drdropops ofs of chrom

chromic acid to ic acid to the t'e" Note and record the color of the t'e" Note and record the color of the soltithe soltion on on on the data sheet"the data sheet" epeat this procedre for /-'tanol$ 2-'tanol$ and

epeat this procedre for /-'tanol$ 2-'tanol$ and 2-methyl-2-propanol"2-methyl-2-propanol"

66

66CACA7#7#3O3ON6N666 ChChroromimic ac acicid id is *s *erery cy cororrorosisi*e*e" " AnAny y spspilill sl shoholld 'd 'e ie immmmedediaiatetelyly flshed %ith %ater"

CH CH₂₂ OHOH   CH CH     OH OH

(4)

Phenols Phenols

Phenols are closely related to alcohols 'ecase of the presence of the hydroyl (

−

OH) OH) !rop" !rop" 3n3n

phenols$ ho%e*er$

phenols$ ho%e*er$ the hydroyl the hydroyl !rop is !rop is directly 'onded directly 'onded to an to an aromatic !rop$ aromatic !rop$ sch as sch as 'enene"'enene" Phenol componds often ha*e crios 't sefl properties" Some are fond in preser*ati*es or Phenol componds often ha*e crios 't sefl properties" Some are fond in preser*ati*es or medications

medications.. #he chemistry of phenols is different than that of alcohols" Concentrated soltions #he chemistry of phenols is different than that of alcohols" Concentrated soltions of the compond phenol are ite toic and can case se*ere 'rns"

of the compond phenol are ite toic and can case se*ere 'rns" In this In this experiment, we experiment, we areare using an aqueous solution of phenol.

using an aqueous solution of phenol.

66

66CACA7#7#3O3ON6N666 PhPhenoenol l is is totoiic c anand d %i%ill ll cacasse e 'r'rns ns to to ssinin" " E*E*en en ththo!o!h h %e %e arare e ssinin!! an aeos soltion of phenol$ any contact shold 'e thoro!hly %ashed an aeos soltion of phenol$ any contact shold 'e thoro!hly %ashed %ith lar!e antities of

%ith lar!e antities of %ater" %ater" =ear safety !lasses =ear safety !lasses at all times iat all times in then the la'oratory"

la'oratory" eport all eport all accidents to accidents to the instrthe instrctor"ctor"

333"

333" PhysiPhysical Propertcal Properties of Phenolsies of Phenols

F"

F" PlaPlace /5 dropce /5 drops of phens of phenol solol soltition inton into a test to a test t'e" 'e" Add /-Add /-2 ml of dic2 ml of dichlohloromromethethaneane"" ecord the o'ser*ations for sol'ility on the data sheet"

ecord the o'ser*ations for sol'ility on the data sheet"

3?"

3?" ChemicChemical Propertial Properties of es of PhenolPhenolss Phenol

Phenols react diffes react differentlrently than alcohols" y than alcohols" #his is %hy they are !i*en their o%n fnct#his is %hy they are !i*en their o%n fnctional !ropional !rop and are not technic

and are not technically Galcoally Galcohols", hols", =e %ill see thi=e %ill see this differes difference in the chromic acince in the chromic acid test and thed test and the ferric chloride test"

ferric chloride test" A"

A" ChChroromimic Acc Acid id #e#estst

Phenols can 'e oidied %ith chromic acid$ 't they !i*e different types of prodcts than Phenols can 'e oidied %ith chromic acid$ 't they !i*e different types of prodcts than those formed from alcohols" #he chromic acid test is descri'ed a'o*e$ and the same reslts those formed from alcohols" #he chromic acid test is descri'ed a'o*e$ and the same reslts are epected for a positi*e test (a 'le-!reen soltion is formed)"

are epected for a positi*e test (a 'le-!reen soltion is formed)"



"" Place /5 drops of acetone in a test t'e" Add F drops of phenol and 2 drops ofPlace /5 drops of acetone in a test t'e" Add F drops of phenol and 2 drops of chromic acid to the t'e" Note and record the color of the soltion on the data sheet" chromic acid to the t'e" Note and record the color of the soltion on the data sheet"

(5)

No

Notete.. 3n 3n ththe e inintetererest st of of titimeme$ $ ththis is phphenoenol l epepererimimenent t cacan n 'e 'e cacarrrrieied d ot ot at at ththe e sasameme time as the alcohol eperim

time as the alcohol eperiments" ents" Conslt instrctor if Conslt instrctor if there is a pro'lem"there is a pro'lem"

66

66CACA7#7#3O3ON6N666 ChChroromimic ac acicid id is *s *erery cy cororrorosisi*e*e" " AnAny y spspilill sl shoholld 'd 'e ie immmmedediaiatetelyly flshed %ith %ater"

;"

;" :e:errrric Chic Chloloriride tede testst Addition of aeos ferri

Addition of aeos ferric chloride to a c chloride to a phenol creates a colored phenol creates a colored soltion" soltion" 8ependin! pon8ependin! pon the strctre of the phenol$ the color can *ary from !reen to prple"

the strctre of the phenol$ the color can *ary from !reen to prple"

I"

I" Place 2Place 25 drop5 drops of s of the fthe ferric erric chlorichloride solde soltion tion into into a test a test t'e" t'e" Add F Add F drops drops of pheof phenolnol soltion"

soltion" Note and record any Note and record any o'ser*ations on the o'ser*ations on the data sheet"data sheet" 3t is clear that som

3t is clear that some of e of the procedthe procedres %ill reres %ill reire some timire some time to e to o'sero'ser*e the reslts*e the reslts" " #he %ell-#he %ell- prepared

prepared stdent$ stdent$ %ho %ho has has read read the the la'oratory la'oratory eercise eercise in in ad*ance$ ad*ance$ may may realie realie that that the the phenolphenol test

tests can 'e carried ot at the sams can 'e carried ot at the same time some of the othe time some of the other tests arer tests are 'ein! done" e 'ein! done" #hese it#hese itemsems need not 'e tested seentially

need not 'e tested seentially" " As the instrctor iAs the instrctor if yo need help"f yo need help"

UNKNOWN UNKNOWN

O'tain an nno%n sample %hich is one of the follo%in!. /-'tanol$ 2-'tanol$ O'tain an nno%n sample %hich is one of the follo%in!. /-'tanol$ 2-'tanol$ 2-methyl-2- propanol

propanol or or aeos aeos phenol" phenol" 7sin! 7sin! the the information information and and no%led!e no%led!e !ained !ained drin! drin! thisthis la'oratory$ and 'y tiliin! yor critical thinin! sills$ determine the identity of this nno%n" la'oratory$ and 'y tiliin! yor critical thinin! sills$ determine the identity of this nno%n" >o can assme that if a test %as not performed on a s'stance$ the s'stance did not react %ith >o can assme that if a test %as not performed on a s'stance$ the s'stance did not react %ith the rea!ent"

the rea!ent"

>or report mst inclde completion of the second data sheet %hich otlines the procedre for >or report mst inclde completion of the second data sheet %hich otlines the procedre for de

detetermrminininin! ! ththe e nnnno%o%n" n" >o sho>o shold ld mamae e a a hyhypotpothehesisis s anand d ththen en desdesi!i!n n or or seselelect ct anan eperi

eperiment %hich %ilment %hich %ill spport or in*alil spport or in*alidate yor hypothesdate yor hypothesis" is" #o *erify the concl#o *erify the conclsion of yorsion of yor n

nno%nno%n$ $ yo yo msmst t ha*ha*e e at at lealeast st thrthree ee epeperierimenments ts desdesi!ni!ned ed to to chechec c andandJor *erifJor *erify y yoyorr hypotheses"

hypotheses" Please 'e 'rief 't Please 'e 'rief 't clear and complete %ith clear and complete %ith yor hypotheses$ planned iyor hypotheses$ planned in*esti!ations$n*esti!ations$ and conclsion"

(6)

DATA SHEET I DATA SHEET I

8ate Name

A

Allccoohhoolls s & & PPhheennoollss PPaarrttnneerrss

Solubility: Solubility:

Eperiment

Eperiment eetthhaannooll //--''ttaannooll 22--''ttaannooll 2-methyl-2- 2-methyl-2- propanol

propanol //--ooccttaannooll pphheennooll

Sol'ility in Sol'ility in H H22OO   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le Sol'ility in Sol'ility in CH CH22ClCl22   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le   CompComp letely letely Sol'le Sol'le   PartiaPartia lly Sol'le lly Sol'le   3nsol3nsol 'le 'le Chemical Properties: Chemical Properties: E

Eppeerriimmeenntt eetthhaannooll //--''ttaannooll 22--''ttaannooll 2-methyl- 2-methyl-2-propanol

2-propanol phenol phenol

Lcas Lcas #est #est Chromic Acid Chromic Acid #est #est :erric :erric Chloride #est Chloride #est

(7)

8A#A SHEE# 33 8A#A SHEE# 33

8

8aatteeKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKK NNaammeeKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKK K A

Allccoohhoolls s & & PPhheennoollss PPaarrttnneerrKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKK K

UNKNOWN #

UNKNOWN # KKKKKKKKKK KKKKKKKKKK



;e sre to record the nm'er of yor nno%n here6;e sre to record the nm'er of yor nno%n here6 /

/"" AA" " HHyyppootthheessiiss..

;" Planned 3n*esti!ation. ;" Planned 3n*esti!ation. C" O'ser*ations (data). C" O'ser*ations (data). 8" Conclsion. 8" Conclsion. 2

2"" AA" " HHyyppootthheessiiss..

;" Planned 3n*esti!ation. ;" Planned 3n*esti!ation. C" O'ser*ations (data). C" O'ser*ations (data). 8" Conclsion. 8" Conclsion. 1

1"" AA" " HHyyppootthheessiiss..

;" Planned 3n*esti!ation. ;" Planned 3n*esti!ation. C" O'ser*ations (data). C" O'ser*ations (data). 8" Conclsion. 8" Conclsion. B

B"" AA" " HHyyppootthheessiiss..

;" Planned 3n*esti!ation. ;" Planned 3n*esti!ation. C" O'ser*ations (data). C" O'ser*ations (data). 8" Conclsion. 8" Conclsion.

(8)

salicylic acid salicylic acid OH OH C C O O OH OH EPO# SHEE# EPO# SHEE# 8ateKKKKKKKKKKKKKKKKKK NameKKKKKKKKKKKKKKKKKKKKKKKKK 8ateKKKKKKKKKKKKKKKKKK NameKKKKKKKKKKKKKKKKKKKKKKKKK A

Allccoohhoolls s & & PPhheennoolls s PPaarrttnneerrKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKK K Ans%er the follo%in! estions.

Ans%er the follo%in! estions. /"

/" 9y 9y 7nno%n 7nno%n (KKKKKK) (KKKKKK) %as. %as. (circle (circle all all that that apply)apply) /-;7#ANOL 2-;7

/-;7#ANOL 2-;7#ANOL #ANOL 2-9E#H>2-9E#H>L-2-POPANOL L-2-POPANOL PHENOLPHENOL 2"

2" SalSalicyicylic acilic acid$ sho%d$ sho%n 'elon 'elo%$ col%$ cold 'e ('td 'e ('t$ it %asn$ it %asnMt) Mt) sed as an nsed as an nno%nno%n" " 8es8escricri'e %ha'e %hatt yo

yo %o%old ld seeseeJleJlearn as arn as yo Ganalyyo Ganalyed, this s'sted, this s'stancance e if it if it %er%ere e yoyor r nnno%n in no%n in thethe follo%in!.

follo%in!.

Sol'ility in %ater. Sol'ility in %ater.

:eCl

:eCl11 #est. #est.

1"

1" =hat res=hat reslts %olts %old yo epld yo epect froect from the reacm the reaction of /-tion of /-propanopropanol %ith eal %ith each of the foch of the follo%illo%in!n! Lcas rea!ent.

Lcas rea!ent.

Chromic acid rea!ent. Chromic acid rea!ent.

B"

B" AlcoholAlcohols are s are more more sol'sol'le ile in %atn %ater ther than hyan hydrocardrocar'ons a'ons are ire in %atn %ater" er" =hy=hy

F"

F" =hy does t=hy does the rle fohe rle for solr sol'ilit'ility for alcy for alcohols depohols depend pon thend pon their moleir moleclar seclar sieie

"

" 9o9ost st pepeopople le fifindnd$ $ in in ththis is eepeperirimementnt$ $ ththat at ththe e reresslt lt fofor r ththe e sosoll'i'ilility ty of of phphenenol ol inin dichlo

dichlorometromethane is that it is insol'hane is that it is insol'le" le" #his does not seem to mae sens#his does not seem to mae sense to s$ as e to s$ as 'oth are'oth are or!ani

or!anic and it c and it shold 'e sol'lshold 'e sol'le" e" (e*i(e*ie% yor reslte% yor reslts for alcohols in dichlos for alcohols in dichlorometromethane")hane") Eplain %hy it appears to 'e insol'le"