Experiment 17 alcohol.docx

7/25/2019 Experiment 17 alcohol.docx

1/23

Experiment 7

Title:Properties of Alcohol

Name:Chong Zheng Yee ( P1 )

ID No.:1404800

Subject:UDEC 1224 CHEM!"#Y $A%A"Y

Name of Partner:"'n Herh $i !i' "ing *'i

Date:+ ,U$Y 201-

Lecturer:Dr. Moh''/ Ain''n


2/23

Objectives :

(i) "o st/ the phsic'l 'n/ cheic'l properties of 'lcohols.

(ii) "o i/entif the t3o nno3n li5i/s fro their e6perient'l o7ser'tions.

(iii) "o st/ the /ifference 7et3een pri'r 'lcohols secon/'r 'lcohols 'n/

terti'r 'lcohols.

Introuction :

Alcohols occr 3i/el in n'tre 'n/ h'e 'n in/stri'l 'n/ ph'r'cetic'l

'pplic'tions. n in/str 'lcohol is se/ 7oth 's ' solent 'n/ 's ' st'rting 'teri'l for

pro/ction of c'r7onl copon/ 'n/ c'r7o6lic 'ci/ (,ohn E. McMrr 2012).

#etriee/ fro 9 ,ohn E. McMrr (2012). Organic Chemistry, Eighth Edition, International

Edition,pp.:28

Alcohols occp ' centr'l position in org'nic cheistr. "he c'n 7e prep're/ in'rios 3's sch 's h/r'tion of 'lene h/ro6l'tion of 'lene re/ction of c'r7onl

copon/ re/ction of c'r7o6lic 'ci/ or ester 'n/ ;rign'r/ re'ction. Ho3eer 'nother

etho/ is se/ for the snthesis of eth'nol (CH


3/23

Alcohols 're org'nic copon/s th't cont'in one or ore h/ro6l (#>&H)

fnction'l grop 7on/e/ to ' c'r7on 'to th't is not 7on/e/ to ' c'r7onl c'r7on (C?&). f

the h/ro6l grop is 7on/e/ to ' 7enene ring it is cl'ssifie/ 's phenol 3hich 3ill h'e

/ifferent properties cop're to 'lcohols. At sch phenols is not sit'7le to 7e se/ in this

e6perient. n '//ition 'lcohols c'n 7e cl'ssifie/ into three s7cl'sses 3hich 're pri'r

(1@) 'lcohol secon/'r (2@) 'lcohol 'n/ terti'r (&H) grop 'tt'che/.

#etrie/ fro 9

http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_iological_Em

phasis/Chapter_!"#$%_Chapter_"#$%_Introduction_to_organic_structure_and_&onding_I

/'ection_".(#$%_)unctional_groups_and_organic_nomenclature

Bor'll 'lcohol 're colorless li5i/ in roo teper'tre. "heir elting point 'n/7oiling point 're higher th'n siil'r sie of 'l'ne 'lene 'n/ 'lne /e to its '7lit to for

h/rogen 7on/ 3ith &H grop. "he o6gen ten/ to pll the electron fro the h/rogen

en'7les the for'tion of tepor'r /ipole/ipole inter'ction. %esi/es th't the '7ilit to for

h/rogen 7on/ 'lso 'es lo3er ol'r 'ss of 'lcohol sol7le in 3'ter. As the &H grop

of 'lcohol c'n for interolecl'r h/rogen 7on/ 3ith 3'ter olecles. Ho3eer 3hen the

length of the h/roc'r7on ch'in of 'lcohol incre'se/ the sol7ilit of 'lcohol in 3'ter

/ecre'se/. "his is 7ec'se 3hen the sie of the h/ropho7ic h/roc'r7on ch'in (nonpol'r

p'rt) incre'ses the pol'rit of &H grop 3ill 7e c'ncelle/ ot.

"here 're soe cheic'l tests to /istingish 7et3een 1o 2o'n/


4/23

'n'ltic'l etho/s h'e repl'ce/ it. $c's re'gent is ' soltion of 'nh/ros inc chlori/e

($e3is 'ci/) in concentr'te/ h/rochloric 'ci/. t is se/ 's ' re'gent to test 'lcohols 'n/

cl'ssif the 'ccor/ing to their re'ctiit. "he re'ction is ' s7stittion re'ction 3here the

chlori/e of the inc chlori/e 3ill 7e repl'ce/ 7 the h/ro6l grop of the 'lcohol. "he

re'ctiit of the 'lcohol 3ith $c's #e'gent is e'sre/ 7 the /egree of tr7i/it 3hich

' 'r fro colorless to tr7i/ (M'/hli' Ach'r' 2012). "he positie reslt (for'tion

of tr7i/ soltion) h'ppens /e to the for'tion of chloro'l'ne 3hich is 'n insol7le soli/.

Bor'll terti'r 'lcohol 3ill fors the precipit'te f'ster th'n secon/'r 'lcohol 3here's '

pri'r 'lcohol /oes not for precipit'te. "he 'lcohol st'rting 'teri'l st 7e sfficientl

sol7le in '5eos enironents of the $c's re'gent for the re'ction to t'e pl'ce. "hs

onl 3'tersol7le 'lcohols of lo3 olecl'r 3eight 3ol/ proi/e positie reslts in this

test

!ii" #$romic aci test

Chroic 'ci/ test is 'lso no3n 's ,ones &6i/'tion. Historic'll 't 14


5/23

!iii" %eaction &it$ metallic soium

Alcohols is ' 3e' 'ci/s 3hich 3ill re'ct 3ith et'llic so/i. "he h/ro6l grop

'cts 's ' proton /onor 'n/ rele'se electron to for 'n 'lo6i/e ion. Alo6i/e ions 3ill then

re'cts 3ith et'llic so/i to for so/i 'lo6i/e. "he 'lo6i/e ions th't /issole/ in 'n

'lcohol is ' strong 7'se 3hich s'e 's h/ro6i/e ion in 3'ter."his re'ction 3ill c'li7r'te

h/rogen g's. "he pri'r 'lcohol 3ill h'e the f'stest r'te of c'li7r'tion of h/rogen g's

follo3e/ 7 secon/'r 'n/ terti'r 'lcohol.

n this e6perient the pri'r 'lcohol se/ is eth'nol secon/'r 'lcohol is isopropl

'lcohol 3hile terti'r 'lcohol is t7tl 'lcohol. "heir strctre is sho3n 7elo39

Eth'nol sopropl 'lcohol t7tl 'lcohol

#$emicals :

eth'nol (C2H-&H) isopropl 'lcohol (C


6/23

Proceures :

!(" Solubilit) of (lco$ols

1. n three sep'r'te /r test t7es '7ot 1 $ of e'ch of the follo3ing9 eth'nol isopropl

'lcohol 'n/ t7tl 'lcohol 3's pl'ce/.

2. A7ot 2 $ of 3'ter 3's '//e/ to e'ch t7e i6e/ 'n/ o7sere/.


7/23

%esults :

!(" Solubilit) of alco$ols

H/roc'r7on &7ser'tion Conclsion

Eth'nol !ol7le in 3'ter 'n/ for

colorless soltion

!ol7le in 3'ter

sopropl 'lcohol !ol7le in 3'ter 'n/ for

colorless soltion

!ol7le in 3'ter

t7tl 'lcohol !ol7le in 3'ter 'n/ for

colorless soltion

!ol7le in 3'ter

Unno3n A !ol7le in 3'ter 'n/ for

colorless soltion

!ol7le in 3'ter

Unno3n % !ol7le in 3'ter 'n/ forcolorless soltion

!ol7le in 3'ter

!*" Lucas test

H/roc'r7on &7ser'tion #e'ction e5'tion Conclsion

Eth'nol "he colorless soltion

re'ins nch'nge/ 'fter

he'ting.

Bo re'ction 7et3een

eth'nol 'n/ $c's

re'gent.

sopropl 'lcohol "he soltion trns clo/

'fter he'ting for -

intes.

C


8/23

'ci/ is '//e/. Cr&4= 10 H=

< CH


9/23

%77les of colorless g's

're pro/ce/.

2C2H-&B' = H2 h/rogen g's is

rele'se/ fro the

re'ction 7et3een

eth'nol 'n/ so/i.

#'te of re'ction is f'st

sopropl 'lcohol "he re'ction is o/er'te.

%77les of colorless g's

're pro/ce/.

2C


10/23

'lcohol to /issole in 3'ter interolecl'r h/rogen 7on/ing 7et3een 3'ter olecles 3ill

first 7e 7roen /o3n to 'e ' l'rge sp'ce for the long h/roc'r7on ch'in 'lcohols.

Ho3eer onl the &H grop of the 'lcohol 're '7le to for 7'c the interolecl'r

h/rogen 7on/ing 3ith 3'ter 3hile the h/roc'r7on ch'in of 'lcohols 3ill not for

h/rogen 7on/ing 3ith 3'ter olecles. Hence ' lot of origin'l h/rogen 7on/ings th't

3ere 7roen e'rlier /i/ not repl'ce/ 7 ne3 ones. nste'/ I'n /er *''ls forces 7et3een the

h/roc'r7on ch'in 'n/ the 3'ter olecles 3ol/ repl'ce the h/rogen 7on/ing. As ' reslt

not enogh h/rogen 7on/s 're refore/ to copens'te 7'c the energ for the h/rogen

7on/s th't h'/ 7een 7roen e'rlier. *hen this /isrption 7ec'e l'rge enogh the 3'ter

olecles 3ol/ repelle/ the 'lcohol olecles effectiel to refor the h/rogen 7on/ing.

"hs the 'lcohol 3ill not sol7le in 3'ter. "his e6pl'ine/ 3h the sol7ilit of 'lcohols

/ecre'se/ 3hen sie of the h/roc'r7on ch'in of 'lcohols incre'se. (Chegi/e.co. 201-).

%'se/ on the t'7le 7elo3 the 'lcohols 3hich cont'ins ore th'n 8 c'r7ons 're insol7le in

3'ter.

#etriee/ fro 9

http://chemed.chem.purdue.edu/genchem/topicreview/&p/*organic/alcohols.html

t7tl 'lcohol still c'n /issole/ e'sil in 3'ter 7ec'se it h's 7r'nche/ 'll grop.

"his fe'tre re/ces the srf'ce 're' of the h/ropho7ic p'rt 'n/ 'ing it sol7le in 3'ter.

Be6t eth'nol 'n/ isopropl 'lcohol 're sol7le in 3'ter 7ec'se the sie of their h/roc'r7on

ch'in is s'll enogh. %oth nno3n A 'n/ % 3ere sol7le in 3'ter 3hich e'ns th't the
http://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/alcohols.htmlhttp://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/alcohols.html


11/23

're 'lcohol 3hich consists of 8 or less c'r7on 'to. "he e6perient'l reslt 're sho3n

7elo39


12/23

"he e6perient'l reslts for p'rt A 're sho3n 7elo39.

Eth'nol sopropl

'lcohol

t7tl

'lcoho

l

Unno3n A Unno3n %


13/23

Gor p'rt % 3hen colorless t7tl 'lcohol is '//e/ 3ith $c's re'gent 'n inst'nt re'ction

occr 'n/ positie reslt 3's o7t'ine/ 3here tr7init fore/ 'n/ the soltion trns clo/

/e to the for'tion of chloro'l'ne 3hich is 'n insol7le soli/. Be6t3hen isopropl

'lcohol '//e/ 3ith $c's re'gent the soltion re'ins nch'nge/ 7efore he'ting 7t 'fter -

intes of he'ting positie reslt 3's o7t'ine/ 3here tr7init 3's fore/ 3hich trns the

soltion clo/ ."his e'ns th't the re'ction 7et3een secon/'r 'lcohol 'n/ $c's re'gent is

slo3er th'n terti'r 'lcohol 's it re5ire/ he't. Grtherore 3hen eth'nol is '//e/ 3ith

$c's re'gent the colorless soltion re'ins the s'e 7efore 'n/ 'fter - intes of he'ting.

"his is 7ec'se pri'r 'lcohol /o not re'ct 3ith $c's re'gent. Ap'rt fro th't nno3n A

h'/ siil'r o7ser'tion 's isopropl 'lcohol 3here's nno3n % h'/ siil'r o7ser'tion 's t

7tl 'lcohol.

"he e6perient'l reslt for p'rt % !before $eatin+"'re sho3n 7elo3 9


14/23

"he e6perient'l reslt for p'rt % !after $eatin+"'re sho3n 7elo3 9

Eth'nol

negative

test

sopropl

'lcohol

positive

test

t7tl

'lcohol

positive

test

Unno3n A

positive test

Unno3n %

positive test

$c's re'gent is 7'sic'll ' soltion 3hich is fore/ 7 the co7in'tion of HCl 'n/ ZnCl2.

n this c'se inc chlori/e 'cts 's c't'lst. Bor'll 'lcohol 'n/ $c's re'gent re'cts 's follo3s 9

Eth'nol sopropl

'lcohol

t7tl

'lcoho

l

Unno3n A Unno3n %


15/23

#etriee/ fro 9http://academics.wellesley.edu/Chemistry/chem*""la&/Orgo_+a&_anual/%ppendi-/Classii

cationests/alcohol.html

"he cheic'l re'ctions for eth'nol isopropl 'lcohol 'n/ t7tl 'lcohol 3ith $c's

re'gent is 's follo3s 9

"he gener'l ech'nis for this re'ction is 9

Eth'nol

Isoprop

yl

t-butyl

alcohol
http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/ClassificationTests/alcohol.htmlhttp://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/ClassificationTests/alcohol.htmlhttp://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/ClassificationTests/alcohol.htmlhttp://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/ClassificationTests/alcohol.html


16/23

#etriee/ fro 9 http://organicchem.org/oc*we&/la&/e-p/o-id/lucas.pd

#e'ction for $c's test is ' !B1ncleophilic s7stittion. n the first step the proton

(H=) fro H/rochloric 'ci/ (HCl) 3ill proton'te the &H grop of the 'lcohol foring the

o6oni ions 3hich is nst'7le. "hen &H2='ccept 'n electron 'n/ le'e the grop to for

3'ter olecle. n ne6t step c'r7oc'tion fore/ 3ol/ re'ct 3ith Cl

to for the 'llpro/ct. "he re'ctiit of 'lcohols in $c's test is /eterine/ 7 the st'7ilities of the

c'r7oc'tion intere/i'tes.

"he c'r7oc'tion st'7ilit of 'lcohols 're 'rr'nge/ in /ecre'sing or/er 's follo3s9

Higher st'7ilit of c'r7oc'tion 3hich h'e higher re'ctiit to3'r/ $c's re'gent.

!ince terti'r c'r7oc'tion is ore st'7le the 3ill n/ergo re'ction 'n/ for tr7i/ soltion

f'ster cop're to secon/'r c'r7oc'tion. Pri'r 'lcohol /o not re'ct 3ith $c's re'gent

7ec'se pri'r c'r7oc'tion is the nst'7le. "hs the cl'sses of 'lcohol for nno3n A 'n/

nno3n % col/ 7e /eterine 3ith this infor'tion. Unno3n A 3hich re5ire he'ting to

for 'll chlori/e is ' secon/'r 'lcohol 3hile nno3n % 3hich for 'll chlori/e

ie/i'tel is ' terti'r 'lcohol.
http://organicchem.org/oc2web/lab/exp/oxid/lucas.pdfhttp://organicchem.org/oc2web/lab/exp/oxid/lucas.pdf


17/23

Gor p'rt C 3hen t7tl 'lcohol 3's tre'te/ 3ith chroic 'ci/ the soltion trns

fro colorless to or'nge /e to presence of Cr:=ions 3hich sho3s ' neg'tie reslt. Be6t

3hen isopropl 'lcohol 3's '//e/ 3ith chroic 'ci/ t3o l'ers soltion fore/ 3ith

greenish soltion on top 'n/ /'r color on 7otto in/ic'ting ' positie reslt. Moreoer

3hen eth'nol 3's '//e/ 3ith chroic 'ci/ the soltion trne/ fro colorless color to '

7l'c l'er. "he 7l'c l'er is 'ct'll the /'r green color it is h'r/ to /ifferenti'te

7ec'se the light is not enogh in the l'7or'tor. "hs it is 'ct'll sho3ing ' positie reslt.

Ap'rt fro th't nno3n A sho3s the positie reslt 3ith green color soltion fore/ in

chroic test 3hile nno3n % sho3s neg'tie reslt.

n the re'ction 7et3een 'lcohol 'n/ chroic 'ci/ ' positie reslt 3ill gies ' green

color ch'nge 7ec'se the or'nge color of Cr:=

ions in i6tre 're re/ce/ to green colorCr


18/23

Ho3eer chroic test c'n onl /ifferenti'te ' terti'r 'lcohol 3ith pri'r or

secon/'r 'lcohol 7ec'se 7oth pri'r 'n/ secon/'r 'lcohol c'n 7e o6i/ise/ 7 Cr:=ions.

Hence fro this test 3e c'n i/entif nno3n % 's terti'r 'lcohol 3here's nno3n A is

pri'r or secon/'r 'lcohol.

"he re'ction of pri'r 'lcohol 3ith chroic 'ci/ is sho3n 7elo3 9

"he re'ction of secon/'r 'lcohol 3ith chroic 'ci/ is sho3n 7elo3 9

#etriee/ fro 9 http://www.harpercollege.edu/tm-

ps/chm/100/dgodambe/thedisk/qual/chromic.htm

"he cheic'l re'ction 7et3een eth'nol 'n/ chroic 'ci/ 9
http://www.harpercollege.edu/tm-ps/chm/100/dgodambe/thedisk/qual/chromic.htmhttp://www.harpercollege.edu/tm-ps/chm/100/dgodambe/thedisk/qual/chromic.htmhttp://www.harpercollege.edu/tm-ps/chm/100/dgodambe/thedisk/qual/chromic.htmhttp://www.harpercollege.edu/tm-ps/chm/100/dgodambe/thedisk/qual/chromic.htm


19/23

#etriee/ fro 9http://science.uvu.edu/ochem/inde-.php/alpha&etical/c0d/chromic0acid/

"he ech'nis of for'tion of chroic 'ci/ is sho3n 7elo3 9

#etrie/ fro 9http://www.name0reaction.com/1ones0o-idation

"he ech'nis of re'ction 7et3een secon/'r 'lchohol 'n/ chroic 'ci/ is sho3n 7elo39
http://science.uvu.edu/ochem/index.php/alphabetical/c-d/chromic-acid/http://www.name-reaction.com/jones-oxidationhttp://www.name-reaction.com/jones-oxidationhttp://science.uvu.edu/ochem/index.php/alphabetical/c-d/chromic-acid/http://www.name-reaction.com/jones-oxidation


20/23

#etriee/ fro 9 http://www.name0reaction.com/1ones0o-idation

Gor p'rt D 'll tpes of 'lcohol se/ in this e6perient 3ill re'cts 3ith et'llic

so/i to pro/ce h/rogen g's /e to the presence of &H grop.

Eth'nol isopropl 'lcohol t7tl 'lcohol

Unno3n A Unno3n %

Gor eth'nol 9 2C2H-&H = 2B'2C2H-&B' = H2

Gor isopropl 'lcohol 9 2C


21/23


22/23

%eference :

1. Ac'/eics.3ellesle.e/. 201-. ests or %lcohols. K&B$BEL A'il'7le

't9http9'c'/eics.3ellesle.e/Cheistrche211l'7&rgo$'7M'n'lAppen/i

6Cl'ssific'tion"ests'lcohol.htl. KAccesse/ 0+ Agst 1-L.

2. Chee/.che.pr/e.e/. 201-.%lcohols and Ethers. K&B$BEL A'il'7le

't9http9chee/.che.pr/e.e/genchetopicreie37p2org'nic'lcohols.htl.

KAccesse/ 0+ Agst 1-L.


23/23

12. 333.cheh'en.org. 201-.+a&oratory **: 2roperties o %lcohols. K&B$BEL

A'il'7le 't9http9333.cheh'en.orgche102l'7CHE102E22!11.p/f.

KAccesse/ 0+ Agst 1-L.

1

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