laporan kimia organik ii baru

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EXPERIMENT REPORT

ORGANIC CHEMISRTY II

ALDEHYDE AND KETONE

BY :

META WIDYAS KARTIKA (083194003)

DEWI RACHMAWATI (083194012)

SE I DIAN S (083194024)

ASRO IYAH (08319403!)

PENDIDIKAN KIMIA PL"S 2008

#"R"SAN KIMIA

AK"LTAS MATEMATIKA DAN ILM" PENGETAH"AN ALAM

"NI$ERSITAS NEGERI S"RABAYA

2010



A% TITLE : A&' *' + A,' K -., + R / - .,+

B% OB#ECTI$ES :1. Know the principle reaction of carbonyl compounds2. Know the difference reaction to aldehydes and ketones

3. Know the type of simple chemical test to distinguish aldehydes and ketones

C% BASIC THEORY

The carbonyl group consists of a carbon atom bonded to an oxygen atom by a double

bond.Compounds containing a carbonyl group are called carbonyl compounds . This group

includes the aldehydes and ketones deninston! 2""3: 3#3$. %ldehydes and ketones are one of

the oxidation products of the alcohols. &ach of these compounds contain a carbonyl group a

carbon atom double bonded to an oxygen atom$.

'n /&' *' + the carbonyl group is always located at the end of the carbon chain

carbon(1$. 'n -., + the carbonyl group is located within the carbon chain of the molecule.

Thus! in ketones the carbonyl carbon is attached to two other carbon atoms. )owe*er! in

aldehydes the carbonyl carbon is attached to at least one hydrogen atom+ the second atom

attached to the carbonyl carbon of an aldehyde may be another hydrogen or a carbon atom.

The structure of aldehydes and ketones. a$ Thegeneral structure of an aldehydes and a ball(and(stick model of the aldehyde propanal. b$ Thegeneral structure of a ketone and a ball(and stick model of the ketone propanone.

A&' *' + and -., + are polar compounds because of the polar carbonyl group.

,ecause of the dipole(dipole attractions between molecules! they boil at higher temperatures

than hydrocarbons or ethers that ha*e the same number of carbon atoms or are of e-ui*alent

molecular weight. ,ecause they cannot form intermolecular hydrogen bonds! their boiling

points are lower than those of alcohols of comparable molecular weight.



The presence of hydrogen atoms! it makes aldehyde is easily oxidi ed or in other

words! the aldehyde is a strong reducing agent. ,ecause ketones do not ha*e this particular

hydrogen atom! it is *ery difficult to oxidi e ketones. /nly a *ery strong oxidi ing agent such

as a solution of potassium manganate 0''$ potassium permanganate solution$ that can

oxidi e ketones ( and e*en then with a mechanism that is not neat! with a break C(C bonds .sually aldehydes react faster than ketones toward a similar reagent. This is because

the atoms of the aldehyde carbonyl is more strongly protected than the atoms of the carbonyl

of ketones.to difference aldehyde and ketone was use :

T.&& ,+ / ,- (+ &5 6 . - +-)Tollens reagent containing! %g )3$ 24/). Tthis compound is made from a solution

of sil*er '$ nitrate. This compound formed by inserting a drop of solution of sodium

hydroxide to a solution of sil*er '$ nitrate produces a precipitate of sil*er '$ oxide! and then

add 5ust enough dilute ammonia solution to dissol*e the re(deposition.To perform the test with Tollens reagent! a few drops of aldehyde or ketone is inserted

into the newly created Tollens reagent! and heated slowly in a hot water bath for se*eral

minutes. %ldehyde gi*e a colorless solution produces a precipitate of sil*er gray! or a sil*er

mirror in the test tube and ketone is no change

%ldehyde reduct sil*er ion in %g )3$ 24/) to sil*er metal. ,ecause the solution is

alkaline! it is itself oxidi ed to aldehyde with a salt and form carboxylic acid.

)alf(reaction e-uation for the reduction of ion diamminperak '$ to sil*er are as

follows:

%nd the e-uation half(reaction of oxidation of an aldehyde in alkaline conditions! ie

6ith combining teo of them will produce a complete reaction e-uation:

T 7+ . & , +.&7- ., . B , ' - + +.&7- .,

7ehling solution and ,enedict8s solution is a *ariant of which is ensensial samesolution. ,oth contain copper ions ''$. 7ehling solution containing copper ions ''$

dicompleks with tartrate ions in the solution of sodium hydroxide. Complexing ion copper ''$

with tartrate ions to pre*ent the deposition of copper ''$ hydroxide.,enedict8s solution containing copper ions ''$ which form complexes with citrate ions

in a solution of sodium carbonate. %gain! Complexing the copper ions ''$ can pre*ent the

formation of a precipitate ( this time deposits of copper ''$ carbonate. 7ehling solution and

,enedict8s solution used in the same way. % few drops of aldehyde or ketone is added to the

reagent! and the mixture is heated slowly in a hot water bath for se*eral minutes. 9eaction

with aldehide form solution produced a dark red precipitate of copper '$ oxide! and ketone



was no change. This reaction because aldehyde reduction of copper ions ''$ to copper '$

oxide. ,ecause the solution is alkaline! it is itself oxidi ed to aldehyde with a salt of the

corresponding carboxylic acid. The e-uation of the reaction is:

%nd the e-uation for the oxidation of aldehydes in the alkaline condition

Combining two of them will get :

T +- , - , & ' /; ,Testing with this compound describes the reaction of aldehydes and ketones with 2! (

dinitrophenylhydra ine! ben adehida and sikfoheksanon as a test reaction to double bond C ;

/. )ere we also discuss briefly about some other similar reaction known as addition(

elimination reaction or condensation$.2! (dinitrophenylhydra ine often abbre*iated to 2! (< = or 2! (< =). 2! (

dinitrophenylhydra ine solution in a mixture of methanol and sulfuric acid reagent known as

,rady. 'n fenilhidra in! one hydrogen atom in the hydra ine was replaced by a phenyl group!

C>)?. 't is based on a ben ene ring.

R / - .,6ith enter a few drops of aldehyde or ketone! or it could be a solution of aldehyde or

ketone in methanol! into the reagent fenil hidra in. The formation of yellow or bright orange

precipitate indicated a C ; / double bond in an aldehyde or ketone.The reaction of this test is the simplest to an aldehyde or ketone %

C

H

N N

H

1(ben ylidene(2(phenylhydra ine

a-$

C

O

H

a-$

@ ) 2 N

H

a-$

,en aldehyde =henylhydra ine

C

H

N

H

@ )2/

l$

s$



C

H

N

Hs$

C

H

N

Ha-$

@ C) 3 /) a-$

C

H

N

Hs$

1(ben ylidene(2(phenylhidra ine

Aellow Crystal$



This reaction is known as the condensation reaction. Condensation reaction is a

reaction in which two molecules 5oin together accompanied by the loss of a small molecule in

the process. 'n this case! the small molecule is water. %ddition(elimination reaction of

aldehydes and ketones ha*e two uses in testing aldehydes and ketones.This reaction can be used to test the existence of double bond C ; /. C ; / double

bond in an aldehyde or ketone ha*e only orange or yellow sediment.1. This reaction can be used to help identify a particular aldehyde or ketone.2. The precipitate was filtered and washed with! for example! methanol and then

recrystalli ed from a suitable sol*ent! which sol*ent can calm *ary depending on the

nature of aldehydes and ketones. 7or example! we can merekristalisasi products small

aldehydes and ketones from a mixture of ethanol and water.The crystals that formed were dissol*ed in hot sol*ent with a minimum amount. 'f the

solution has cooled! the crystals precipitated again and can be filtered! washed with a little

sol*ent and dried. These crystals will be pure. 'f you know the melting point crystals! then

you can compare it with the theory.

H/&. . 6 R / - .,,romine and chlorine also reacts with methyl ketone produces bromoform and

chloroform its formation is not useful to test the reaction because of bromoform and

chloroform is a li-uid that is not ob*ious$. % general term to refer C)B3 is haloform

haloform reaction$ 7essenden! 1# 2$. 'odoform test is a typical test for methyl ketonecompounds. )ydrogen in alpha position is acidic and its use produces results enolate

anion. 7urther enolate anion can react with the halogen compound halokarbonil for iodine.

A&'.& .,' ,+/- .,

%ldol condensation is a fusion reaction in the atom or molecule in which different molecules

and form new compounds are more complex. 'n general! condensation reactions occur in the

liberation of water! alcohol! or other compounds that stabiol. Komndensasi aldol reaction

occurs in the aldehyde(aldehyde ha*ing an alpha ) atoms! namely ) atoms are bound by the

C atoms directly bonded to the carbonyl group! when reacted with dilute alkali a/)$ or

DnCl2. 'n compound 3(hydroxy butane there are two functional groups! namely group(C)/and(/) groups. Therefore! these compounds ha*e properties such as aldehydes and alcohols.

) 3C C

O

CH 3

propan(2(one

@ 3'2 @ 3/) ( → ) 3C C

O

OH

acetic acid

@ 3'( @ ) 2/@ C)' 3

'odoformyellow precipitate$



7rom the word aldehyde and alcohol of said aldol. 3(hidrosibutanal 6hen heated! the

dehydration process occurs and produces krotonaldehida. The example with acetaldehyde is :

D% E<"IPMENT AND S"BSTANCES

1% E=7 >6 ,-• Test tube• Thermometer • Conical flask ?" ml• )irsch funnel• ,uchner funnel• 7ilter paper • 9ubbing alcohol burner • Epherical flask • 9efluks

2% S7?+-/, +

• %cetaldehyde• Cyclohexanon• 7ormalin• 'sopropyl alcohol• Fethanol• &thanol• 7ehling reagent• a/) 1" G sulotion• a/) ?G sulotion• %g / 3 ?G sulotion• ) /) ?G sulotion• a)E/ 3 saturated• )Cl sulotion•

=henylhidra yn reagent• 'odium solution• Cool water

)3C C) C)

2) 3C C )

/

) 3C C )

/

@

δ−

δ+

/ (

C )

/

) @

) (

) 3C C) C) 2

/)

C )

/

heat) 2/

C) 3 C) C) C

/

)

adol crotonaldehyde



• =ipe kapiler



E% PROCED"RE

1%T.&& ,+ - +-

a. make tollent reagent

- =our to test tube- =our 2 drops a/) ?G- Fixed well the mixture

- %dd ) /) 2G drop by drop and still shake until the precipitate can soluble precisely

b. Test with tollens reagent

- %dd 2 drops ( %dd 2 drops ( %dd 2 drops ( %dd 2 drops,en aldehide %cetone Cyclohexanone 7ormalin

- Ehake the mixture carefully-

9est for 1" minutes- 'f there isnHt reaction! heat the test tube in water bath3?IC ( ?"IC$ for ? minutes

2% & , - +-

2 ml %g /3 ?G

7orm brown precipitate

=recipitate soluble

T.&& ,+ / ,-

=repare test tube

Test tube%

Test tube,

Test tubeC

Test tube<

Test tube %There is a

grey clumpwhich drift

Test tube ,There isn’t

reaction

Test tube CThere isn’t

reaction

Test tube <There is

silver mirrorin around test

tube wall

=repare test tube

Test tube% Test tube, Test tubeC Test tube<

Test tube %

There is a dark red precipitate and by the

time change intocuprum mirror

Test tube ,(,.-

/5/ &/?& )

Test tube CThere isn’treaction

Test tube <There isn’t

reaction



- %dd ? ml 7ehling solution in each test tube

- %dd 2 drops ( n( )eptaldehyde ( %dd 2 drops ( %dd 2 drops7ormaldehyde (,.- /5/ &/?& ) %cetone Cyclohexanone

- =ut into boiling water for 1"(1? minutes

3%B +7& - /' - .,

-

- =our in conical flask ?" ml- Cooled in ice water - %dd 2!? ml acetone drop by drop with shaken for ? minutes- %fter ? minutes! add 1" ml ethanol for start crystalisation

- 7ilter that crystal with separating funnel- %dd strong )Cl with drop by drop carefully

4%T +- - P , & *' /; ,

- %dd into each test tube

? ml saturated solutionof a)E/

3

6hite crystal

/bser*ation result:The crystal was lostand the solution is

colorless

? ml phenyl hydra yn

Test tube%

Test tube,

Test tube%

Test tube,

Form yellowcrystal

There isn’treaction

The melting point is 134°



- %dd 1" drops ,en aldehyde ( %dd 1" drops Cyclohexanone

- Close the test tube- Ehake strongly for 1(2 minutes until made crystal

- 7ilter the crystal with filter paper in funnel- 6ash the crystal with cold water clean the crystal- %dd methanol drop by drop for make crystal again- 9ested the crystal until dry about 2 days$- <etermine the melting point

@%O 6 6/ , (- +7?+-/, + + ,.- /5/ &/?& )

- %dd 1!? gram crystal C) 3C//)- =our ml water - <issol*e in conical flask ?" ml- )eated until 3?IC- %dd cyclohexanone drop by drop- Close the flask - Ehake for 2 minutes until cyclohexanone oxim can form

1 gram hydroxylaminehydrocloryne

/bser*ation result



- Cooled the flask in ice water! then filter the crystal with funnel- 6ash with ice water and put on dry filter paper - <etermine the melting point

%H/&. . 6 / - .,

- %dd in each test tubes

- %dd ? drops %cetone ( %dd ? drops isopropyl ( %dd 2(pentanone ( 3(pentanone %lcohol

N.- A5/ &/?&- %dd iodium and shaken until the color of iodium not change again

!% A& . .& .,' ,+/- .,

a. Make krotonaldehyde

- =ut into test tube- %dd "!? ml acetaldehyde- Ehaken well and note the smell from acetaldehyde before reaction$

- ,oiled the mixture for 3 minutes and carefully- ote the smell

3 ml solution of a/) ?G

Test tube%

Test tube,

Test tubeC

Test tube<

Test tube %

There are yellow precipitate !""# and the

smell like medicine

Test tube ,

There are yellow precipitate !"""# and the

smell like medicine

ml a/) 1G

The smell like baloon

Krotonaldehyde

The smell is rancid



b. Determine the melting point (Not Available)

- =ut into conical flask ?" ml- %dd 1 ml acetone- %dd 2 ml ben aldehyde- %dd ? ml a/) ?G- 9efluks the mixture for ? minutes- Cool the flask and collect the crystal produce by ,uchner funnel- The mixture can make crystal again from ethanol- <etermine the melting point

% OBSER$ATION RES"LT

o Treatment/bser*ation 9esult

,efore %fter 1. Test with Tollens 9eagent

'n the test tube! add 2 ml

%g / 3 ?G and 2 drops a/)

?G. %fter that! mixed well themixture. %dd ) /) 2G drop

by drop and still shake until the

precipitate can soluble

precisely. The mixture is call

tollens reagent.

=repare test tube% : ,en aldehyde 2 drops$ @ 1

ml Tollens

%g / 3 ?G ;

Colorless

a/) ?G ;

Colorless

) /) 2G ;

Colorless

,en aldehyde ;

yellow pure

• %g / 3 @ a/) form

precipitate. The colour is

dark brown.• %fter the mixture add

) /) 2G!the precipitate

soluble.• %dd ) /) 1 drops.• The color of that mixture

is colorless.• %fter the mixture! test tube

:

% : form white precipitateand become grey

, : There isnHt precipitate

1" ml &thanol

Felting point



, : %cetone 2 drops$ @ 1 ml

TollensC : Eiclohexanon 2 drops$ @ 1

ml Tollens< : 7ormalin 2 drops$ @ 1 ml

Tollens

%cetone ;

colorless

Eiclohexanon ;

colorless

7ormalin ;colorless

and the solution is

colorless!by the time the

color change to blue.C : The solution is colorless< : form sil*er mirror

2. Test with 7ehling 9eagentFake 7ehling solution 7ehling

test$! 1" ml 7ehling % @ 1" ml

7ehling ,.=repare test tube! 2 drops

solution test and ? ml 7ehling% : 7ormaldehid @ 7ehling @ heat

1" minutes, : %seton @ 7ehling @ heat 1"

minutesC : Eiclohexanon @ 7ehling @

heat 1" minutes< : n()eptanal The solution is

not a*ailable$

7ehling % : Jight

,lue

7ehling , :

Colorless

7ormaldehyd :

Colorless

%cetone :

Colorless

Eiclohexanon :

Colorless

• Fixture of 7ehling % @ ,:− Eolution is dark blue− Contain Cu 2@

• % : The solution is blue

and there are precipitate.

The color is dark(red and

by the time!form cuprummirror., : There is no reaction!

the solution is still dark

blue.C : There is no reaction!

the solution is still dark

blue.3. ,isulfit %dition

− %dd ? ml saturated solution of

sodium bisulfite! a)E/ 3.− Cool in water − %dd 2!? ml acetone drop by

drop and shake well for ?

minutes.− %dd 2" ml ethanol #>G for

make crystal− 7ilter the crystal− %dd strong )Cl drop by drop in

the crystal.

a)E/ 3 ;

Colorless

6ater ; Colorless

%cetone ;

Colorless

)Cl ; Coloress

&tanol #>G ;

Colorless

• %fter cooled in water! the

solution still colorless.• %fter add acetone! the

solution is colorless.• %fter add etanol #>G! the

solution make a crystal!the

color is white.• %fter add )Cl! the crystal

is lost and there are only

solution which colorless.

. Test with =henylhidra in

− ? ml phenylhidra in add in 2

test tube% : 2!? ml =henylhydra in @

,en aldehyde,: 2!? ml =henylhidra in @

Eiclohexanon

=henylhidra in ;

/range

,en aldehyde ;

Aellow pureEiclohexanon ;

• % : there are solution !the

color is orange and there

are turbit yellow crystal., : There is not reaction!

so only there are orange

solution.



− %fter that close the test tube and

shake strogly.− 7ilter the crystal with separating

funnel.− 6ash with cold water!next− 6ash with methanol− 9asted and determine the melt

point

Colorless

Fetanol ;

Colorless

Cold 6ater ;

Colorless

• Crystal in test tube %

separated with funnel.• Crystal in test tube % ;

Aellow Turbid @@$.• %fter add cold water! the

crystal are little soluble

and the color is yellow @

@$• %fter add methanol! the

crystal which little

soluble!form crystal again

and the color is yellow but

more white.• The melting point is

132 / C.?. )aloform 9eaction

− 3 ml solution of a/) ?G put

into 2 test tube.% : %ceton @ 'odium, : 'soprophyl %lcohol @

'odium

a/) ?G ;

Colorless

'odium ; <ark

,rown

Aellowish

%ceton ;

Colorless

'sopropyl %lcohol

; Colorless

• % : 6hen a/) @

%ceton!the solution is

Colorless., : 6hen a/) @

'sopropyl %lcohol! thesolution is Colorless.

• %fter add iodium% : The solution change

into turbid solution and by

the time !the color of

solution change into dark

brown yellowish like

iodium.There are precipitate!the

color is yellow. need 2 ml

'odium$, : Jike test tube %!after

add iodium the solution is

turbid! by the time

solution change into dark

brown yellowish like

'odium. need 2 ml



'odium$There are precipitate and

the color is yellow.• The different of test tube %

and ,! there are :

% : Jittle =recipitate, : Fuch =recipitate

>. %lcohol condentation

− ml a/) 1G put into test

tube− %dd "!? ml acetaldehyde− Ehake well

− ,oiled the mixture for 3minutes

a/) 1G ;

Colorless

%cetaldehyde ;

Colorless!

the smell like

baloon

• The mixture form solution

and the color is yellow @

@$.• The smell is pungent.



PICT"RES ABO"T ALCOHOL AND KETONES EXPERIMENT :

1. Tollent reagent

$icture 1% reaction between formalin and tollent reagen

6ith the tollent reagent! formaline formaldehyde$ can make sil*er mirror precipitate.

2. Fehling reagent

$icture no.& % formaldehyde' acetone' and siclohe(anone whenreact with fehling reagen

$icture no.3 % acetone and siclohe(anone not

react with fehling

Ketone canHt be react with fehling agent



$icture no.4 % Formaldehyde react with fehling

%ldehyde compounds can react with fehling to form dark red precipitate.

$icture no.) % Formaldehyde which e(periences more o(idation

6hen aldehyde compounds more oxidation! so they can form cuprum mirror in thewall of tube.

$icture no. *% reaction benedict with formaldehyde

,enedict is slower than fehling. Eo if they react with fehling! so they are not reactfastly.

%lthough! if aldehyde compounds react with benedict! they must be to form dark red precipitate too.



. !is"l#ite adition

$icture no. + % reaction between ,a- / 3 " 0cetone withethanol

'n this reaction! after a)E/ 3 @ %cetone add some ethanol!it is form crystal which the color is white.

=icture no. : result when compound pict. add strong)Cl

6hen solution picture add some strong )Cl! so that thesolution will be colorless.

$. Test will phenylhydra%yn

$icture no. % solution of phenylhydra2yn

$icture no.1 % reaction between phenylhydra2yn withben2aldehide

6hen phenylhydra yn react with ben aldehyde! it make precipitatewhich color is yellow.

$icture no.11 % reaction between phenylhydra2yn with siclohe(anone

Eiclohexanone canHt be reart with phenylhydra yn.



$icture no.1& % result of the phenylhidra2on

&. 'alo#orm rea tion

$icture no.13 % compare acetone and isopropyl alcohol when

add iodium in ,a/-

The result of this paper is that in acetone is contain more precipitate than isopropyl alcohol and the color is more dark thanisopropyl alcohol

. Al ohol ondensation

$icture no.14 % the result of reaction between

0cetaldehyde with ,a/-



G% ANALYSIS

1% T.&& ,+ R / ,- T +-1.1 =repare tollens 9eagent.

7irst! add 2 ml %g / 3 ?G and 2 drops a/) ?G in the test tube. This produce is

brown precipitate Eil*er /xide %g 2/$. Then! it is added drop by drop ) /)2G until sediment soluble precisely! is signed with disappeared brown sediment

and solution becomes colorless. The compound formed here is 2%g ) 3$24/) .

'f the solution is add ammonium hydroxide too much! testing to differences

aldehyde and ketone with this reagent will be fail.R / - ., :

2%g / 3 @ 2 a/) %g 2/ @ 2 a / 3 @ ) 2/

%g2/ @ ) /) 2%g ) 3$24/) @ 3) 2/

1.2 <istinguish %ldehydes and Ketones with tollens reagentThe next procedure is prepare test tube test tube %! ,! C! and <$ and fill with

Tollent 9eagents! then filled each test tube with 2 drops of ben aldehyde in test tube

%! 2 drops of acetone in test tube ,! 2 drops of cyclohexanon in test tube C! and 2

drops of formalin in test tube <. Ehake and rest it for ten minute! if there are no

reaction! place in water bath for ? minutes to speed up reaction. %nd the result of this

experiment are:

Test Tube % : 7orm white lump drift in solution and become orange when heated. 'tshow that Eil*er %g$ was formed! because Tollens 9eagent %g ) 342$/)$ can

oxidi e ben aldehyde become ,en oic %cid and become sil*er %g$ in test tube

%. Eil*er Firror in test tube % was disappeared because the properties of

ben aldehyde is contain oils.R / - ., I, T +- T7? A:

Test Tube , : Eolution is colorless and not form sil*er mirror because acetone can not

oxidation by Tollent reagent.R / - ., :

@ %g[( ) 3)2]/) → no 9eaction) 3C C CH 3

O

Acetone

,rown

C

O

H

@ %g[ ) 3$2]/) → %g↓ + C

O

OH

@ ) 3 @ ) :@ @ ) 2/

ben.aldehyde ben.oic acid



Test Tube C : Eolution is colorless and not form sil*er mirror because siclohexanon

can not oxidation by Tollent reagent! but a long time! it change become blue

color.R / - .,:

Test Tube < : 7orm Eil*er Firror in wall of Test Tube. 't is Eil*er %g$! because

7ormalin can reduction Tollens 9eagent %g ) 342$/)$ becomes Eil*er and

7ormalin oxidation becomes 7ormiat %cid.

R / - .,:

The aim of this experiment differenteate between aldehyde and keton by testing

Tollens 9eagent.

2% T +- - & , R / ,-The first! prepare 7ehling 9eagent by mixturing 7ehling % CuE/ $ and 7ehling ,

a/) @ Eodium =otassium Tartarat$. 7ill 9eagent in 3 test tubes Test tube %!,! and

C$! then add each test tube with formaldehyde! acetone and siclohexanon. =lace the

test tube in water bath and heat for 1"(1? minutes. The heating is used to speed up

reaction. The result of this experiment:Test tube %: The color of solution is blue! form dark(red sediment and by the time

also form cuprum mirror. 7ormaldehid can oxidation becomes 7ormiat %cid and

Cuprum ''$ /xide can reduction becomes Cuprum '$ /xide. 'f cuprum excessi*e

oxidation because heating ! it will form cuprum mirror.R / - .,:

Test tube ,: Eolution has blue color and not form dark(red sediment because acetone

can not oxidation by 7ehling reagent.R / - .,:

Test tube C: Eolution has blue color and not form dark(red sediment because

siclohexanon can not oxidation by 7ehling reagent.

R / - .,:

@ %g[( ) 3)2]/) → no 9eaction

O

) C

O

H

@ %g[( ) 3)2]/) → %g↓ + ) C

O

OH

@ ) 2/ @ ) :@ @ ) 3

) 3C C CH 3

O

@ Cu/ → no reaction

Eiclohexanon

) C

O

H

@ Cu/ → ) C

O

OH

@ Cu2/ ↓

dark(red sediment

@ ) 2/



@ Cu/ → no reaction

O

The aim of this experiment differentiate between aldehyde and keton by testing

7ehling 9eagent. ote:6e also use benedict reagent! but when react with solution % ,en aldehyde$ not

form dark(red precipitate. 't occurs because the benedict reagent is not too reacti*e.

Eo! the reaction is slower than 7ehling 9eagent. 't need a long time for happen

reaction.

3% B +7& - A'' - .,Connical 7lask ?" ml filled ? ml the bored sodium bisulfit solution and cool in ice

water. The process of cooling must be done carefully to a*oid free ing. Then! add 2!?

ml acetone drop by drop with shake. %fter fi*e minutes!add 1" ml etanol for starting

crystalitation. The color of crystal is white . The crystal is sodium 2(hydroxipropane(

2(sulfonate. Then! add many drops of strong clorida acid to form acetone again. The

reaction is re*ersible.R / - .,:

The aim of this experiment is showing the differences of aldehyde and keton.

&specially! the bisulfite nucleofilik addition reaction of acetone.

4% T +- - > ,*& ' /; ,7irst! two test tube filled ? ml phenylhydra ine and each filled with 2!? ml test

solution ,en aldehyde and Eiclohexanon$ and shake for 1(2 minutes in order to

solution can mixture perfectly and form crystal. Then! filter the solution to separate

) 3C C

OH

SO 3 Na

CH 3

sodium 2(hydroxypropane(2(sulfonate

@ )Cl → ) 3C C

O

CH 3

propan(2(one

) 3C C CH 3

O

@ a)E/ 3 @ C2) ? /) → ) 3C C CH 3

OH

SO 3 Na

Eodium 2(hydroxypropane(2(sulfonateAcetone



crystal and filtrat. The crystal is 1(ben ylidene(2(phenylhydra ine. 6ash the crystal

with water. 't make the crystal little soluble. To make crystal again! add little

methanol. Fethanol and water act as sol*ent. ext! determine melting point of the

crystal with Lblock logamM. To determine it! we must wait three days in order to the

crystal really dry and pure. This reaction is called Condensation reaction! the fusing of two moleculs form an molecul with free water molecul ) 2/$. The 9esult of this

experiment :

Test Tube % : Eolution has orange color and form yellow crystal. The yellow sediment

is 1(ben ylidene(2(phenylhydra ine. There are yellow crystal to show a carbonil

compounds. The initial melting point is 12" / C and it is constant at 132 / C.

R / - .,:

C

H

N N

H

1(ben ylidene(2(phenylhydra inea-$

C

O

H

a-$

@ ) 2 N

H

a-$

,en aldehyde =henylhydra ine

C

H

N

H

@ ) 2/ l$

s$


Aellow Crystal$

1(ben ylidene(2(phenylhydra ineAellow Crystal$

C

H

N

Hs$

C

H

N

Ha-$

@ C) 3 /) a-$



Test tube , : Eolution has orange color and not form yellow sediment. The solution is

=henylhydra ine.R / - .,:

The aim of this experiment is testing a carbonil compounds and differences between aldehyde and ceton.

@% H/&. . 6 R / - .,%There are 2 test tube. Test tube % contain 3 mJ sodium hydroxide ? G colorless and add ? drops acetone

colorless. 'n this reaction the solution is colorless. %fter that add iodium solution dark

brown yellowish$ until the color of iodium not ceace need 2 mJ iodium$. The

solution change into turbid solution and by the time the color of solution change into

dark brown yellowish like iodium and form yellow precipitate in base of tube. This is

iodoform. 6hen iodoform is formed! there are sting smell. This smeel is special smeel

of iodoform. This reaction e-uation is:

a-$

O @ ) 2 N

H

a-$

→ no reaction

Eiclohexanon

methanol1(ben ylidene(2(phenylhidra ine

C

H

N

Hs$

1(ben ylidene(2(phenylhidra ine

=ale Aellow Crystal$

) 3C C

O

CH 3

propan(2(one

@ 3'2 @ 3/) ( → ) 3C C

O

OH

acetic acid

@ 3'( @ ) 2/@ C)' 3

'odoformyellow precipitate$



Test tube , contain 3 mJ sodium hydroxide ? G colorless and add ? drops isoprophyl

alcohole colorless. 'n this reaction the solution is colorless. %fter that add iodium

solution dark brown yellowish$ until the color of iodium not ceace need 2 mJ

iodium$. Jike test tube %! after add iodium is turbid! by the time the solution change

into dark brown like iodium and form yellow precipitate in base of tube. This isiodoform. 6hen iodoform is formed! there are sting smell. This smeel is special smeel

of iodoform. This reaction e-uation is:

% A&'.& C.,' ,+/- .,

mJ sodium hydroxide 1 G colorless put in test tube and add "!? mJ acetaldehyde

colorless. %fter that shake well. The smell in this rection is like baloon this smell is

smell of acetaldehyde that not be react$. This reaction e-uation is :

%fter that boiling the mixture during 3 minutes and carefully. The color of mixture is

be yellow and this smell is pungent. 't show that this mixture experince condentation

and form crotonaldehyde. This reaction a-uation is :

) 3C C C) 3

/

acetone/) (

) 3C C

/

/)

@ 2 C)' 3

acetic acidiodoformyellow precipitate

) 3C C) C) 3' 2

/)isoprophyl alcohole

) 3C C C) 3

/

acetone/) (' 2

) 3C C) C) 2) 3C C )

/

) 3C C)

/

@

δ−

δ+

/ (

C )

/

) @

) (

) 3C C) C) 2

/)

C )

/

heat) 2/

C) 3 C) C) C

/

)

adol crotonaldehyde

) 3C C)

/

acetaldehyde

/) () 3C C

)

/

acetaldehyde



H% DISC"SSION

'n the first experiment tollens test$! there are de*iation between the result of

experiment with theory. ,ase on theory aldehyde ben aldehyde$ is positi*e reaction with

tollens reagent and form sil*er mirror. ,ut in our experiment it not happen. 'n our experiment!

reaction between be aldehyde with tollens reagent form white hank and became grey hank. 't

is caused by the properties of ben aldehyde is similar with oil! so cohession process with the

wall(tube do not happen.

'n the second experiment fehling test$! when we use benedict reagent to oxida ing

aldehyde to form dark red sediment! tis reaction is longer than use fehling test. 't may be this

benedict reagent is made more long! but fehling reagent is new made.

'n the fourth experiment testing with phenylhydra in$! based on theory the melting

point of ben aldehyde phenylhydra on is 1?> oC. ,ut from our result we get the melting point

of ben aldehyde phenylhydra on is 132 oC. 't is caused not so pure the crystal of substances

and because it heaped up with other crystal that wet! so it is not so dry.

I% CONCL"SION%fter we did experiment! we get conclusion:1. ,en aldehyde and formalin aldehyde$ is oxida ed with reagent tollens and form

sil*er mirror! but acetone and siclohexanone ketone$ is not.2. 7ormaldehyde aldehyde$ is reacted with reagent fehling and form dark red

precipitate and if cuprum is more oxida ing with heating$! it will form cuprum

mirror. ,ut aceton and siclohexanone ketone$ is not be oxidation.3. Ketone acetone$ react with Eodium bisulphite form Keton asetone$ bisulphite as

salt that is not dissol*ed in organic sol*ent$. 't form white hablur.



. ,en aldehyde aldehyde$ is react white phenylhydra in and form hablur. %fter this

hablur is react with etanol is form yellow sediment. ,ut siclohexanone with

phenylhydra in and etanol not form yellow sediment.?. %cetone ketone$ is react with iodium and form iodoform. 'odoform is yellow

precipitate and has specific smell.>. %setaldehyde aldehyde$ experience condentation and form crotonaldehyde. The

color of Crotonaldehyde is yellow and has pungent smell.

#% ANSWER O <"ESTION

1% a. R / - ., . T.&& ,+ - . 6/&' '

b. R / - ., . & , - H >-/&' *'

c. > .'7 , . /'' - ., .6>.7,'+ . / -., ? +7& -

d. > .'7 , . ? ,;/&' *' > ,*& *' /;.,

) C

O

H

@ %g[( ) 3)2]/) → %g↓ + ) C

O

OH

@ ) 2/ @ ) :@ @ ) 3

) 3C C CH 3

O

@ a)E/ 3 → ) 3C C CH 3

OH

SO 3 Na

C

O

H

a-$

@ ) 2 N

H

a-$

C

H

N

H

) 3CH 2C

H 2C

H 2C

H 2C

H 2C C

O

H

@ Cu/ → @ Cu2/ ↓ @ ) 2/C>) 13 C

O

H



e. > .'7 , . + &. /,., . 6

f. - +- , .'. . 6 /- 2 > ,-/,.,

2%

3% Aes! it can

identify C) 3 ( C) 2 ( /)! used triiodometana iodoform$

9 ( /) @ ' 2@ /) ( C)' 3 N yellow sediment$

Oust! secunder alchohol can produce C)' 3 triiodometana$ but etanol is the only

kind of simple prymer alcohol that can be known.

't can differences between isopropyl alcohol and n(butil alcohol for isopropyl

alcohol. 't can produce C)' 3 because it is secunder alcohol. ,ut! n(butil

alcohol can not produce C)' 3 because it is prymer alcohol.

O@ )2 /) →

OH

NHOH→ NOH

heat

C)3 C)2)2C C) C)3

/

@ 3'2@ 3/) (

C) 3 C) 2 C) 2

C C' 3

/

@ 3)2/

@ 3'(

) 3C C) C) 2) 3C C )

/

) 3C C)

/

@

δ−

δ+

/ (

C )

/

) @

) (

) 3C C) C) 2

/)

C )

/

heat) 2/

C) 3 C) C) C

/

)

adol crotonaldehyde



4% To differences between aldehid and ketones.

@% a. by using iodoform testing! we can differences 3(pentanon and 2(pentanon can

produce yellow sediment C)' 3$ but 3(pentanon can not produce yellow sediment

C)' 3$.

b. testing iodoform! 3(pentanon can produce yellow sediment C)' 3$ but pentanol

cannot produce yellow sediment C)' 3$.

c. reaction of ben aldehyde with tollen regent or fehling reagent is positi*e.. it can

oxidation. ,ut acetofenon with tollen regent or fehling reagent is negati*e. 't

cannot oxidation.

% Keton react with Eodium bisulphite form Keton bisulphite as salt that is not

dissol*ed in organic sol*ent

T + R / - ., +

/ /)

P P P

C) 3 QC QC) 3 @ a)E/ 3 R C)3 QC QC)3

P

a 3E/

%cetone sodium bisufit acetone bisulfit

'f the %cetone bisulphit is reacted with chloride acid! it will be %cetone! Eodium

chloride! and water.

T + R / - ., +

/) /

P PP

C) 3 QC QC) 3 @ )Cl R C) 3 QC QC) 3 @ aCl @ E/ 2 @ ) 2/

P



a 3E/

acetone bisulfit Chloride acid %cetone sodium chloride

!% ,ased on theory:

the melting point of penilhydra on is 1#!? o

the melting point of 2! (dinitrophenylhydra on is 1# (2"2 oC

Eo! the meltig point of 2! (dinitrophenylhydra on is higher than phenylhydra on.

the melting point of ben aldehyde penilhydra on is 1?> oC

the melting point of ben aldehyde 2! (dinitrophenylhydra on is 23#(2 1 oC

Eo! the meltig point of ben aldehyde 2! (dinitrophenylhydra on is higher than

phenylhydra on.

8% The rule of sodium acetat is to pull S hydrogen



K% RE ERENCES

7essenden dan 7essenden. 1##1. imia /rganik 5ilid 1 . &rlangga. Oakarta.

'r. <ar5anto!dkk. 1# . -impunan 6ahan uliah 7lmu imia /rganik . =urwokerto :

ni*ersitas Oenderal Eoedirman.

6ilbraham dan Fatta. 1##2. $engantar imia /rganik dan -ayati . ,andung : 'T,.

)! )ard. 1# #. imia /rganik 8ntuk 8niversitas . Oakarta : &rlangga.

Eykes! =eter. 1# #. $enuntun 9ekanisme :eaksi imia /rganik . Oakarta : ramedia.

Jouis 7 7ieser U Fary. 1#> . $engantar imia /rganik 7 . ,andung : <iwantara.

Tim =enyusun. 2""#. $enuntun $raktikum imia /rganik 1 . Eurabaya: Ourusan Kimia

7F'=% &E%.

,asuki. 0kdehid dan keton . http:VVbasuki.webnode.comVnewsV*isitors(noticeV. Eabtu! #

october 2"1".1?.""6',.

%nonim. 0ldehid dan keton . http:VVnaynienay.wordpress.comV2"" V12V"1Valdehid(dan(

ketonV. Eabtu! # october 2"1".1?.""6',

yabatini' 0nnisa. 0ldehid ;an eton. http:VVannisanfushie.wordpress.comV . Eabtu! #

october 2"1".1?.""6',

%nonim. 0ldehid dan keton . http:VVwww.chem(is(

try.orgVmateriWkimiaVsifatWsenyawaWorganikValdehidWdanWketonVreaksiWadisiWeliminas

iWaldehidWdanWketonV. Eabtu! # october 2"1".1?.""6',.

http://basuki.webnode.com/news/visitors-notice/


http://naynienay.wordpress.com/2007/12/01/aldehid-dan-keton/



http://annisanfushie.wordpress.com/

http://www.chem-is-try.org/materi_kimia/sifat_senyawa_organik/aldehid_dan_keton/reaksi_adisi_eliminasi_aldehid_dan_keton/






http://annisanfushie.wordpress.com/




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