Alkohol (Repaired)

8/9/2019 Alkohol (Repaired)

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I EXPERIMENT TITTLE : Alcohol and Phenol

II EXPERIMENT DATE : April, 24th 2015 at 1!00 p!"

III END #$ EXPERIMENT : April, 24th 2015 at 1%!00 p!"

I& EXPERIMENT P'RP#(E : Di)tin*+i)h propertie) o penol and alcohol

'nder)tandin* an- reaction and rea*ent that can

.e +)ed to di)tin*+i)h phenol and alcohol

co"po+nd

& /A(I TE#R

Alcohol

In chemistry, an alcohol is any organic compound in which the hydroxyl

functional group (-O H) is bound to a saturated carbon atom. The term alcohol

originally referred to the primary alcohol ethyl alcohol (ethanol), the predominant

alcohol in alcoholic beerages.!lcohols, the general formula for which is "nH#n$%OH.

Ph-)ical and che"ical propertie)

!lcohols hae an odor that is often described as &biting' and as &hanging' in

the nasal passages. thanol has a slightly sweeter (or more fruit-lie) odor than the

other alcohols.

In general, the hydroxyl group maes the alcohol molecule polar . Those

groups can form hydrogen bonds to one another and to other compounds (except in

certain large molecules where the hydroxyl is protected by steric hindrance of

ad*acent group). This hydrogen bonding means that alcohols can be used as protic

solents. Two opposing solubility trends in alcohols are+ the tendency of the polar OH

to promote solubility in water, and the tendency of the carbon chain to resist it. Thus,

methanol, ethanol, and propanol are miscible in water because the hydroxyl group

wins out oer the short carbon chain. utanol, with a four-carbon chain, is moderately

soluble because of a balance between the two trends. !lcohols of fie or more carbons

http://en.wikipedia.org/wiki/Chemistryhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Hydrogenhttp://en.wikipedia.org/wiki/Saturation_(chemistry)http://en.wikipedia.org/wiki/Carbonhttp://en.wikipedia.org/wiki/Ethyl_alcoholhttp://en.wikipedia.org/wiki/Alcoholic_beverageshttp://en.wikipedia.org/wiki/Hydroxyl_grouphttp://en.wikipedia.org/wiki/Polar_moleculehttp://en.wikipedia.org/wiki/Hydrogen_bondhttp://en.wikipedia.org/wiki/2,2,4,4-tetramethyl-3-t-butyl-pentane-3-olhttp://en.wikipedia.org/wiki/Steric_hindrancehttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Misciblehttp://en.wikipedia.org/wiki/N-Butanolhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Hydrogenhttp://en.wikipedia.org/wiki/Saturation_(chemistry)http://en.wikipedia.org/wiki/Carbonhttp://en.wikipedia.org/wiki/Ethyl_alcoholhttp://en.wikipedia.org/wiki/Alcoholic_beverageshttp://en.wikipedia.org/wiki/Hydroxyl_grouphttp://en.wikipedia.org/wiki/Polar_moleculehttp://en.wikipedia.org/wiki/Hydrogen_bondhttp://en.wikipedia.org/wiki/2,2,4,4-tetramethyl-3-t-butyl-pentane-3-olhttp://en.wikipedia.org/wiki/Steric_hindrancehttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Misciblehttp://en.wikipedia.org/wiki/N-Butanolhttp://en.wikipedia.org/wiki/Chemistry


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such as pentanol and higher are effectiely insoluble in water because of the

hydrocarbon chains dominance. !ll simple alcohols are miscible in organic solents.

!lcohols, lie water, can show either acidic or basic properties at the -OH

group. ith a p/ a of around %0-%1, they are, in general, slightly weaer acids than

water , but they are still able to react with strong bases such as sodium hydride or

reactie metals such as sodium. The salts that result are called al3oide), with the

general formula 2 O3 4$.

la))iication o Alcohol)

In a primary (%5) alcohol, the carbon atom attached to the 6OH group is bonded to one

other carbon atom. In a secondary (#5) alcohol, it is attached to two carbon atoms and

in a tertiary (75) alcohol to three carbon atoms.

Phenol

8"arbolic acid8 redirects here. It is not to be confused with carbonic acid.

Phenol, also nown as car.olic acid, is an aromatic organic compound with

the molecular formula "0H9OH. It is a white crystalline solid that is olatile. The

molecule consists of a phenyl group (-"0H9) bonded to a hydroxyl group (-OH). It is

mildly acidic and re:uires careful handling due to its propensity to cause chemical

burns.

!lthough similar to alcohols, phenols hae uni:ue distinguishing properties.;nlie in alcohols where the hydroxyl group is bound to a saturated carbon atom, in

phenols the hydroxyl group is attached to an unsaturated aromatic (alternating double

and single bond) hydrocarbon ring such as ben


3/38

Propertie)

=henol is appreciably soluble in water, with about >?.# g dissoling in

%@@@ mA (@.>> 4). Homogeneous mixtures of phenol and water at phenol to water

mass ratios of B#.0 and higher are also possible. The sodium salt of phenol, sodium

phenoxide, is far more water soluble.

2eactions

=henol is highly reactie toward electrophilic aromatic substitution as the

oxygen atoms pi electrons donate electron density into the ring. y this general

approach, many groups can be appended to the ring, ia halogenation, acylation,

sulfonation, and other processes. Howeer, phenols ring is so strongly actiatedC

second only to aniline Cthat bromination or chlorination of phenol leads to

substitution on all carbons ortho and para to the hydroxy group, not only on one

carbon. =henol reacts with dilute nitric acid at room temperature to gie a mixture of

#-nitrophenol and ?-nitrophenol while with concentrated nitric acid, more nitro groups

get substituted on the ring to gie #,?,0-trinitrophenol which is nown as picric acid.

!:ueous solution of phenol is wealy acidic and turns blue litmus slightly to

red. =henol is easily neutrali


4/38

#. Iron(III) "hloride Test.

!ddition of iron(III) chloride dissoled in chloroform (trichloromethane) to a

phenol dissoled in chloroform, gies a colored solution upon addition of

pyridine. Gepending on the structure of the phenol the color of the product can be

most anything from red to iolet. !lcohols do not gie this test.

&I MATERIAL( AND E'IPMENT

A MATERIAL(

% thanol

# %-=ropanol

7 #-=ropanol

? D-utyl alcohol

9 ec-utyl alcohol

0 Tert-utyl alcohol

iclohexanol

> tilen glicol

1 =henol

%@ 2esorsinol

%% O-/resol

%# #-Dapthol

%7 DaOH %@J solution

%? Datrium

%9 == indicator

%0 Aucas reagent

% rom in water

/ E'IPMENT

% Test Tube

# patula7 Grops pippete

"


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@,9 mA or @,#-@,9 gram of ethanol

!dd # mA of water

hae

2ecord the obseration

olubility

@,9 mA or @,#-@,9 gram of n-butyl alcohol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of tert-butyl alcohol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of cyclohexanol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of etyleglicole

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of phenol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram n-butyl alcohol

!dd 9 mA DaOH %@ J solution

hae


olubility

@,9 mA or @,#-@,9 gram cyclohexanol


hae


olubility@,9 mA or @,#-@,9 gram phenol


hae2ecord the obseration

olubility

@,9 mA or @,#-@,9 gram naphtol


hae


olubility

&II EXPERIMENT PR#ED'RE

D E Solubility

$

6

I

J K Reaction with Alkali

L

M

N

#P


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# mA of ethanol

!dd a piece of sodium

!dd == indicator

2esult

# mA of %-propanol


!dd == indicator

2esult

# mA of #- propanol


!dd == indicator

2esult

# mA of o-cresole


!dd == indicator

2esult

# mA of Aucas reagent

!dd 9 drops of !lcohol (%-butanol)

2esult


!dd 9 drops of !lcohol (#-butanol)

2esult


!dd 9 drops of "yclohexanol

2esult


!dd 9 drops of tert-butyl alcohol

2esult

R

(

T

'

&7

X

8

AA

AB ACReaction with Sodium

AD

AE

A$

A6

A

AIA9

A

AL

AM

AN

A#

AP AQLucas Test

AR

A( T+.e 1 T+.e 2

AT

A'

A& T+.e T+.e 4

A7

AXA


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#9 gram chromate !nhydride ("rO7) #9 mA sulfuric acid concentrated

Gilute with 9 mA distilled water

2eagent olution

T+.e I

;Te)t o /+tanol<

=ut in reaction tube

!dd % drop of alcohol solution (%-butanol)hae it until the solution become clear

!dd % drop reagent solution

"olorless

% mA acetone % mA acetone


!dd % drop of alcohol solution (#-butanol)hae it until the solution become clear


"olorless


!dd % drop of alcohol solution (tert-butyl)hae it until the solution become clear


"olorless

% mA acetone

T+.e II

;Te)t o 2=/+tanol<

T+.e III

;Te)t o Tert /+t-l<

% mA acetone


!dd % drop of alcohol solution (tryfenyl carbinol)

hae it until the solution become clear


"olorless

% mA acetone % mA acetone


!dd % drop of alcohol solution (resolsinol)

hae it until the solution become clear


"olorless

% mA acetone

T+.e I&

;Te)t o Tr-phen-l ar.inol<T+.e &

;Te)t o Re)ol)inol<

A8

/A

//

/

BD BE !idation with Ch"omic Acid/$ Rea*ent /ord>ell=7el"an

/6

/

/I

/9


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Gissole in 7 mA of water

!dd bromine solution until the yellow color not change

2ecord the result of obseration

2esult

@.% gram phenol

T+.e I

% or # crystal K % or # solution of phenol

!dd 9 mA water

!dd % or # drop solution of iron (III) chloride

hae it

2ecord the result

2esult

T+.e II

%K# crystal or %K# solution of resolsinol

!dd 9 mA water


hae it

2ecord the result

2esult

T+.e III

%K# crystal or %K# solution #-propanol

!dd 9 mA water

!dd % or # drop solution of iron (III) chlorid

hae it

2ecord the result

2esult

/

/L

/M

/N

/#

/P/

/R

/(

/T

/'

B# B$ Reaction with Phenol and B"omine $ate"

/X

/

/8A

/

D

E

$

6

C% C& Reaction with Phenol and &"on'&&&( Chlo"ide

9

L

M

N

#

P

R

(

T

'


9/38

&III RE('LT #$ EXPERIMENT

&

CW RESULT OF THE EXPERIMENT

4elting =oint (@")J rendemen Gar =urple "rystal


10/38

@,9 mA or @,#-@,9 gram of n-butyl alcohol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of ethanol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of tert-butyl alcohol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of cyclohexanol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of phenol

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram of etyleglicole

!dd # mA of water

hae


olubility

@,9 mA or @,#-@,9 gram cyclohexanol


hae


olubility

@,9 mA or @,#-@,9 gram n-butyl alcohol


hae


olubility

@,9 mA or @,#-@,9 gram naftol


hae


olubility

@,9 mA or @,#-@,9 gram phenol


hae


olubility

% mA acetone

Gissole in 7 mA of water

!dd bromine solution until the yellow color not change

2ecord the result of obseration

2esult

@.% gram phenolT+.e III

%K# crystal or %K# solution #-propanol

!dd 9 mA water


hae it

2ecord the result

2esult

! T"eatment " Result G Reaction Con

clus

ion

H

BI A)te

"

A 4 ol+.ilit-

D

O

=

L

2

T

;

M

N

* thanol

colorless

solution* D-butyl

colorless

solution

* "yclohexana

colorless

solution

* =henol

brown

solution

* !:uadest

colorless

P

F

*

* thanol $ water

colorless soluble

* D-butyl $ water

solorless partial

soluble

* "yclohexanol $

water colorless

not soluble

* thylene gliol $

water colorless

soluble

* =henol $ water

turbid solution (#

layers) not

soluble

!!

!Te)t T+.e I

!"

(a:) $ H#O(l)

→

(a:) $ H#O(l)

!GTe)t T+.e II

!

(a:) $ H#O(l)

→

(a:) $H#O(l)

!Q Te)t T+.e

III

!R (a

:) $ H#O(l)

→

(a:

) $ H#O(l)

!HTe)t t+.e I&

!M-

tha

nol

is

solu

ble

in

wate

r

!

- n-

uty

l is

solu

ble

in

wate

r

!N-

"ycl

ohex

anol

is

not

solu

ble

in $ Hr(a:)

,

* Add . mL wate"* Add , o" + d"o/

solution o) i"on

'&&&( chlo"ide

* eResult

* Add . mL wate"* Add , o" + d"o/

solution o) i"on

'&&&( chlo"ide

Result


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"P

IX EXPLANATI#N

CZ Experiment 1

G! The purpose of first experiment is testing the solubility betweenalcohol and phenol. Qirst we prepare fie test tube. In the first test tube add @.9 mA

colorless ethanol solution and # mA of water. The ethanol solution soluble in water.

The reaction is

D/ (a:) $ H#O(l) →

(a:) $

H#O(l)

G" In the second test tube add @.9 mA colorless n-butyl alcohol solution

and add # mA of water. D-butyl alcohol partial soluble in water. The reaction is

DD (a:) $ H#O(l)→

(a:) $ H#O(l)

G In the third test tube add @.9 mA colorless cyclohexanol solution and

add # mA of water. "yclohexanol not soluble in water. It proing by there is two layer

in the test tube. ;pper layer colorless thic solution and bottom layer colorless

solution. The reaction is

D$ (a:) $ H#O(l)

→

(a:) $ H#O(l)

GR In the fourth test tube add @.9 mA etylenglicol and add # mA water.

tylen glicol soluble in water. The reaction is

GH (a:) $ H#O(l)

→

(a:)

GI In the fifth test tube ad @.9 mA brown phenol solution and add # mA

water. =henol not soluble in water. It proing by there is two layer in the solution.

;pper layer is colorless and bottom layer orange solution.

GS The presence of an electronegatie oxygen atom between a carbon and

hydrogen atom creates a permanent dipole in the alcohol and phenol structure. The

negatie inductie effect of the electronegatie oxygen creates a partial negatie

charge on oxygen and partial positie charges on the carbon atom and hydrogen atom


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attached to oxygen. Gue to the presence of this dipole, alcohols and phenols are

considered to be relatiely polar organic compounds. ecause of the presence of a

dipole, alcohols and phenols can participate in intermolecular hydrogen-bonding (H-

bonding). Intermolecular H-bonding also is a critical determinant of alcohol and

phenol solubility.

G/

GA !lcohol more soluble than phenol. The relatie solubility of alcohols is

dependent on the si


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GO

G= Qrom the explanation aboe, we can concluded that etylen glicol is

most soluble in water because it is alcohol and hae two -OH group. o, it is easily

soluble in water. The arrangement of solubility is etylen glicol, ethanol, n-butanol,

cyclohexanol and phenol. thanol, n-butanol and cyclohexanol has more alyl so it isless solublen than etylen. =henol not soluble in water because the oxygen s electrons

in the p orbital delocalise into the ring, this reduces the phenols ability to mae

hydrogen bonds, which is what solubility in water is about the oxygen uses lone pairs

to mae H bond.

DQ Experiment 2

G2 The purpose of the second experiment is understanding reaction

between alcohol and phenol with alaly. Qirst we prepare four test tube. In the first

test tube add @.9 mA colorless n-butyl alcohol solution and add 9 mA of DaOH %@J

solution. The mixture form two layer solution. ;pper layer is purple solution and

bottom solution is colorless solution. n- butanol not react with DaOH

G (a:) $ DaOH (a:)

↛

GT In the second test tube add @.9 mA colorless cyclohexanol solution and

add 9 mA DaOH %@J solution. The mixture form two layer. ;pper layer is colorlesssolution and bottom layer is colorless. "yclohexanol not react with DaOH

G; (a:) $ DaOH(a:)

↛


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GM In the third test tube add @.9 mA brown phenol solution and add 9 mA

of DaOH %@J solution. The solution become clear yellow thic solution. the reaction

is

G (a:) $ DaOH (a:)

→

$ H#O

GN In the fourth tube add @.9 mA colorless naphtol solution. !nd add 9 mA

DaOH %@J solution. The mixture become dar brown solution and there is blac

sediment. The reaction is

GP (a:) $ DaOH(a:)

→

(a:)

GF The principle of this experiment is solubility of phenol and alcohol in

DaOH solution. One ma*or difference is that phenols are typically about a million

times more acidic than alcohols. !ddition of sufficient a:ueous sodium hydroxide to a

phenol will cause the -OH group of most of the molecules present to be deprotonatedthis will not happen to an alcohol. 4ost phenols are weaer acids than carboxylic

acids and stronger acids than alcohols. hen phenols react with a base the phenol is

conerted into a phenoxide anion (see reactions below). The phenoxide anion is more

soluble in water than the corresponding phenol. "onse:uently, if a water-insoluble

phenol is treated with an a:ueous solution of a base that is strong enough to conert

most of the phenol to the phenoxide anion, that phenol will dissole in the a:ueous

base (as the phenoxide salt).

!

" Qrom the explanation aboe we get the conclusion that phenol and

napthol can react with DaOH solution. ecause phenol is wealy acidic. =henol can

lose a hydrogen ion because the phenoxide ion formed is stabilised to some extent.The negatie charge on the oxygen atom is delocalised around the ring. !lcohol


15/38

which is n-butanol and cyclohexanol can no react with DaOH because there are not

acidic and not base solution.

ED Experiment 3

The purpose of third experiment is understanding reaction between

alcohol and phenol with sodium. e prepare three test tube. In the first test tube add #

mA ethanol and add a piece of sodium metal. The gas release. Then add pp indicator.

The color of solution change from colorless become purple. The function of adding pp

is to now the color changing when the condition of solution change. It is indicated

that the solution become base after adding sodium. The solution become hot. It

indicated that the reaction occur is exotermic. The reaction is

Q # (a:) $ #Da(s)→

# (a:) $

H#(g)

R In the second test tube add # mA %-propanol and a piece of sodium.

The gas release. Then add pp indicator. The color of solution become purple. It is

indicated that the solution become base after adding sodium. The solution become

hot. It indicated that the reaction occur is exotermic.The reaction is

H # (a:) $ #Da(s)→

# (a:)

$ H#(g)

I In the third test tube add # mA of #-propanol and a piece of sodium.

The gas release. Then add pp indicator. The color of solution become purple. It is

indicated that the solution become base after adding sodium. The solution become

hot. It indicated that the reaction occur is exotermic.The reaction is

S # (a:) $ #Da(s)

→

# (a:) $H#(g)

/ If a small piece of sodium is dropped into some ethanol, it reacts

steadily to gie off bubbles of hydrogen gas and leaes a colorless solution of sodium

ethoxide. Qrom the experiment we now that the gas that produce by ethanol is most

than the other. e can write the gas release ethanol U %-propanol U #-propanol.

=rimary alcohol more easily react with sodium than secondary and tertiary. The

arrangement of reactiity is ethanol, %-propanol, #-propanol.


16/38

A !lcohols are only slightly weaer acids than water, with a / a alue of

approximately % V %@ 3%0. The reaction of ethanol with sodium metal (a base) produces

sodium ethoxide and hydrogen gas.

4

D This reaction is identical to the reaction of sodium metal with water.

O

= Howeer, the latter reaction occurs faster because of the increased acidity of

water (/ a alue of % V %@3%9). Aiewise, similar reactions occur with potassium

metal.

L The acidity of alcohols decreases while going from primary to secondary to

tertiary. This decrease in acidity is due to two factors+ an increase of electron density

on the oxygen atom of the more highly0substituted alcohol, and steric hindrance

(because of the alyl groups, which inhibit solation of the resulting aloxide ion).

oth of these situations increase the actiation energy for proton remoal. The

basicity of aloxide ions increases while going from primary to tertiary. This increasein basicity occurs because the con*ugate base of a wea acid is strong. The weaer the

acid, the stronger the con*ugate base. Qrom the explanation aboe we now that the

arrangement of base is #-propanol, %-propanol, ethanol.

ER

ES Experiment 4

T The fourth experiment is to distinguish among primary, secondary, and

tertiary water soluble alcohols with Aucas test. Aucas reagent is a mixture of

concentrated hydrochloric acid and


17/38


!dd 9 drops of "yclohexanol

2esult


!dd 9 drops of tert-butyl alcohol

2esult

M !nd the solution is colorless, means that not react much at all. This indicate

that %-butanol is a primary alcohol. ecause primary alcohols will not react much at

all, since a primary carbocation is so unstable so it will not react with Aucas reagent.

In second tube is filled with % mA Aucas reagent, colorless and added

with 9 drops #-butanol solution, colorless. There is reaction that happen, because it

form two layer colorless solution. The reaction is

N "H7"H(OH)"H#"H7 $ H"lZnCl

2

→ "H7"H("l)"H#"H7

$H#O

P The solution is has two layersKcloudiness in % minute. This indicate that #-

butanol is a secondary alcohol. ecause secondary alcohols will react slowly with

Aucas reagent. econdary alcohols react a bit slower as their carbocations (# degree)

are not as stable as tertiary alcohol.

F In third tube is filled with % mA Aucas reagent, colorless and added

with 9 drops cyclohexanol solution, colorless. There is reaction that happen, because

it form two layer colorless solution. The reaction is

Q!

OH

$ H"l

ZnCl2

→

Cl

$ H#O(l)

Q The solution is has two layersKcloudiness in # minutes after

cyclohexanol added. This indicate that cyclohexanol is a secondary alcohol. ecause

secondary alcohols will react slowly with Aucas reagent. econdary alcohols react a

bit slower as their carbocations (# degree) are not as stable as tertiary alcohol. oth

secondary alcohol in test tube II and test tube III, In the case of secondary alcohols, it

is often the case that the chlorine is attached to the carbon that held the hydroxyl, but

rearrangements are possible. !lso The chlorinated product is usually insoluble in

water(the solent in this reaction), whereas the initial alcohol is usually soluble in

water because of its 6OH group. "loudiness appearing in the reaction mixture is taen

as eidence of a positie reaction.

Q" The tertiary alcohol undergoes the most stable reaction and the primary

alcohol undergoes the least stable reaction. The reaction which normally occurs is a

D% nucleophilic substitution which is a two steps reaction. !lcohols which hae a


18/38

capability to form carbocation intermediates exhibit this reaction. Only econdary and

Tertiary alcohols exhibit D% nucleophilic mechanism.

QG

Q

QQ

QR

QH The two steps which are generally followed in this reaction+

%. In the first step the proton (Fn#$) from Fn"l# will protonate the OH- group of the

alcohol. ater (H#O) attached to the carbon is a weaer nucleophile than "l

("hloride). Thus nucleophile "l- replaces the H#O group forming a carbocation

as its present in excess.#. In the second step the "l- attacs the carbocation and thus forms alyl chloride.

QI Here the first step is generally the slowest step and is the rate

determining step. !s the tertiary carbocation is much stabili


19/38

this reaction is that the polarity significantly enhances the stability of the reaction

intermediate and increases the oerall rate of the reaction. !dditional catalysts are not

necessary. !romatic compounds without the phenol functional group react with

bromine through this mechanism.

QD

QO

Q=

QL

Q2

FS Experiment 7

QT The seenth experiment is reaction of phenol and Qe"l7. This

experiment is to detect the presence of phenolic compounds(phenol). The first tube is

filled with # drops of phenol, brown orange. !nd added with 9 mA of water. !fter that

added by ferric chloride # drops, yellow solution. There is reaction that happen,

because it changing color purple solution. The reaction is

Q;

OH

$ Qe"l7

O Fe

Cl

Cl

QM The solution changing become color purple solution, this indicate that

there is presence of phenolic compounds in phenol. =henol is acidic, and can form the

phenoxide ion. This ion can complex with iron(III) and form a coloured substance.

The complex reaction is

Q 0"0H9OH $ Qe"l7 → WQe(O"0H9)0X7- $ 0H$ $ 7"l- or

QN

QP The second tube is filled with # drops of resorcinol, brown. !nd added

with 9 mA of water. !fter that added by ferric chloride # drops, yellow solution. There

is reaction that happen, because there is changing color from orange solution, after

resorcinol added by water to brown clear solution after added by ferric chloride. The

reaction is

QF


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R!

R

R"

RG The changing color of this reaction, indicate that there is presence of

phenolic compounds in resorcinol. 2esorcinol can form the phenoxide ion. This ion

can complex with iron(III) and form a colored substance.

R The third tube is filled with # drops of #-propanol, colorless. !nd

added with 9 mA of water. !fter that added by ferric chloride # drops, yellow solution.

There is no reaction that happen, because there is no changing color from colorless

solution, after #-propanol added by water to colorless solution after added by ferric

chloride.

RQ

RR

RH $

Qe"l7 →

RI

RS The no changing color of this reaction, indicate that there is no

presence of phenolic compounds in #-propanol. ecause #-propanol is alcohol

compound, alcohol are much less liely to form ions, meaning alcohols cannot

complex the iron(III) ion and therefore cannot form coloured compounds.

R/ The reason use Qerric "hloride (Qe"l7) in the lab to test for the

presence (or in some case absence) of phenols, although some -enols will also yield

positie results. The OH (hydroxy group) which is attached directly to an aromatic

nucleus (en


21/38

but phenol more soluble in strong base lie DaOH. =henol is more acidic

than alcohol so it is react with metallic sodium.

# To distinguish between alcohol and phenol we can use oxidation reaction

with reagent cromate acid also using lucas test with lucas reagent, bromine

water and Qe"l7. =henol with react with three of reagent but alcohol is not

reacted.

R4

XI 'E(TI#N AND AN(7ER

6N+e)tion

% hat conclusions can be drawn regarding alcohol solubility in water, based on

the results of the aboe experimentsY hich of the %-pentanol and %-Heptanol

are more soluble in waterY

2 rite a balanced e:uation showing the solubility of phenol in %@J sodium

hydroxide solutionZ

Qrom the aboe experimental results, which is more acidic, n-hexanol or

phenolY xplain the reasonZ

4 rite the e:uation for the reaction between ethanol and sodiumZ !re the

instructions saying the results of this reactionY

5 ased on the aboe experimental results, how can distinguish between

cyclohexanol and phenolY

% How would the effects of lucas reagent to each of the following compounds+ %-

butanol, cyclohexanol and tert-butyl alcoholY? !mong the following compounds+ %-butanol, triphenyl carbinol, resorcinol,

which one does not undergo oxidation in testing ordwell-ellmanY

@ rite the e:uation of the reaction between phenol and bromine waterZ Dame

the type of reaction that occursZ

6# An)>er

1! horter the chain " is the more easily soluble in water because the hydroxyl

group can form hydrogen bonds with water molecules.

R= hich is difficult soluble in water is %- Heptanol, because %- Heptanol

" group containing as many as 0 so that the chain is getting long and poorly

insoluble in water. ecause more chain can distrupt the hydrogen bond

between alcohol and water

#.

RL + NaOH ⟶ + H 2O

R2

7. =henol is more acidic than n-hexanol, because phenol has a -OH group

attached to the aromatic cyclic chain. o readily reacts with a strong base

O ONa


22/38

DaOH. "yclic aromatic acid chain more than cyclic chain aliphatic alcohols as

can resonate so it is more stable than aliphatic alcohols.

?.2C

2 H

5OH +2 Na⟶2C H

3CH

2ONa+ H

2

R hen drops of == indicator solution turn pin, there are bubbles in the

tube, and the tube was hot.

9. It can distinguish between =henol and !lcohol(cyclohexanol) using bromine

water . It always gies precipitate whiteKyellowKorange with =henols whereas it

does not form any precipitate with alcohols.

0. Aucas reagent toward %-butanol, there is no reaction occur, that[s mean %-

butanol is primary alcohol. Then Aucas reagent toward cyclohexanol, is form

two layer in 9-0 minutes, that[s mean cyclohexanol is secondary alcohol. !nd

Aucas reagent toward ter-butyl , form two layer in less timeKfaster than

cyclohexanol that[s mean ter-butyl is tertiary alcohol.

. =rimary and secondary alcohols can be easily oxidi


23/38

6&RE$ERENE(

R

RN !nonim. #@%9. alcohols and sodium (online)

http+KKwww.chemguide.co.uKorganicpropsKalcoholsKsodium.html (accessed!pril #9th, at #@.@@)

RP !nonim. #@%9. Sodium metal as a reagent in organic chemistry — Master

Organic Chemistry (online)

http+KKwww.masterorganicchemistry.comK#@%%K%@K@Kreagent-friday-sodium-naK

(accessed !pril #9th, at #@.@@)

RF !nonim. #@%9. The Reaction Between Alcohols and Sodium – Chemwiki

(online)

http+KKchemwii.ucdais.eduKOrganic\"hemistryK!lcoholsK2eactions\of\!lcoh

olsKThe\2eaction\etween\!lcohols\and\odium (accessed !pril #9th, at

#@.@@)

H! !nonim. #@%9. Reactions of Alcohols (online)

http+KKwww.cliffsnotes.comKsciencesKchemistryKorganic-chemistry-iiKalcohols-

and-ethersKreactions-of-alcohols (accessed !pril #9th, at #@.@@)

H !nonim. #@%9. the acidity of phenol (online)

http+KKwww.chemguide.co.uKorganicpropsKphenolKacidity.html (accessed !pril

#9th, at #@.@@)H" Qessenden and Qessenden. %1>0. imia Organik! "disi etigas. Ter*emahan

!loysius Hadyana =ud*aatmaa =h. G.. Saarta+ rlangga

HG Tim Gosen /imia Organi. #@%9. #enuntun #raktikum imia Organik $ .

urabaya+;nipress

H

http://www.chemguide.co.uk/organicprops/alcohols/sodium.htmlhttp://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Reactions_of_Alcohols/The_Reaction_Between_Alcohols_and_Sodiumhttp://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Reactions_of_Alcohols/The_Reaction_Between_Alcohols_and_Sodiumhttp://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/alcohols-and-ethers/reactions-of-alcoholshttp://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/alcohols-and-ethers/reactions-of-alcoholshttp://www.chemguide.co.uk/organicprops/phenol/acidity.htmlhttp://www.chemguide.co.uk/organicprops/alcohols/sodium.htmlhttp://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Reactions_of_Alcohols/The_Reaction_Between_Alcohols_and_Sodiumhttp://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Reactions_of_Alcohols/The_Reaction_Between_Alcohols_and_Sodiumhttp://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/alcohols-and-ethers/reactions-of-alcoholshttp://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/alcohols-and-ethers/reactions-of-alcoholshttp://www.chemguide.co.uk/organicprops/phenol/acidity.html


24/38

$ATTAMENT

HG Solubility

HI Tu

HS

H/

=oured @.9 mAcyclohexanol into

test tube III

=oured @.9 mA n- butyl alcohol into

test tube II

=oured @.9 mA

ethanol into test tube

I colourless


25/38

HA

H4

HD

HO

!dded # mA of

water in each test

tube

=oured @.9 mA

phenol into test

tube M brownsolution

=oured @.9 mA

ethyleneglicol into

test tube IM colourless solution


26/38

H=

HL

H2

hae each test tube thanol $ water

colorless solution

(soluble)

n-butyl alcohol $

water colourless

solution (partial


27/38

H

HT

H;

HM

H

HN

HP

HF Reaction with l!ali

phenol $ water

turbid solution (not

soluble two la er

thylene glycol $

water colorless

solution soluble

"yclohexanol $

water colorless

solution not soluble

=rority of solubility of soluble insoble is

ethylene glycol U ethanol U n-butanol U

U


28/38

I!

I

I"

IG

=oured @.9 mA

cyclohexanol into

test tube II

=oured @.9 mA

phenol into test

tube III brown

=oured @.9 mA n-

butyl alcohol into

test tube I


29/38

I

IQ

IR

n-butyl alcohol $

DaOH %@J $

shae colorless

=oured 9 mA DaOH

%@J into each test

tube

=ut @.9 mA naphtol

into test tube IM

bac powder


30/38

IH

II

IS

I/

IA

I4

ID Reaction with "o#iu$

naphtol$ DaOH

%@J $ shae

brownish solution

phenol $ DaOH

%@J $ shae

light yellow thic

cyclohexanol $

DaOH %@J $ shae

colorless solution

n- butyl alcohol and cyclohexanol not react with

DaOH. =henol and na htol react with DaOH


31/38

IO

I=

IL

I2

=oured # mA #-

propanol into test tube

=oured # mA %-

propanol into test tube

=oured # mA ethanol

into test tube I

thanol $ metallic

Da $ phenolptalein

$ shae pin

!dded

phenolptalein

indicator and shae

!dded a small

metallic Da

yellowish colorless $


32/38

I

IT

I;

IM

I

IN

IP

IFS!

S

%C Luca" Te"t

#-propanol $

metallic Da $

phenolptalein $

%-propanol $

metallic Da $

phenolptalein $

2eact arrangement

thanol U %-

propanol U #-


33/38

SG

S

SQ

SR

=oured % mA lucas

reagent $ %-butanol

into test tube I

colourless solution

=oured % mA lucas

reagent into each test

tube colourless

solution

=oured % mA lucas

reagent $ #-butanol

into test tube II

two layers


34/38

SH

SI

SS

%&

%L

%M

%N

%O %P Reaction with Phenol with '(o$ine Wate(

=oured % mA lucas

reagent $

cyclohexanol into test

tube III two layer

"yclohexanol and #-butanol (secondary

alcohol) can react with Aucas reagent proen by

two la ers in solution


35/38

%)

S2

S

ST

S;

SM

SSN

=oured @.9 mA

phenol $ 7 mA of

water $ brominewater into test tube

=oured @.9 mA

phenol $ 7 mA of

water into test

=oured @.9 mA

phenol into test tube

brown solution

phenol $ 7 mA of

water $ bromine

water into test tube upper is colourless,

-


36/38

%*

%+

&

&'

&CReaction with ,henol with I(on -III. Chlo(i#e

&/

/

/Q

=oured # drops of

#-propanol into test

tube III

=oured # drops pf

resolsinol into test

tube II blacish

=oured # drops of

phenol into test tube

I brown solution


37/38

/R

/H

/I

/S

//

/A

/4

/D

/O

Tube I+ # drops of

phenol $ 9 mA of

water $ # drops of

Qe"l7 purple

!dded # drops of

Qe"l7 in each test

tube

!dded 9 mA of

water in each test

tube


38/38

P

/L Tube II+ # drops of

resorsinol $ 9 mA of

water $ # drops of Qe"l7 clear brown

solution

Tube I+ # drops of

#-propanol $ 9 mA

of water $ # dropsof Qe"l7

colorless solution

=henol and

resorsinol react

with Qe"l7 but #-

Alkohol (Repaired)

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