Full Report Nmr

8/18/2019 Full Report Nmr

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UNIVERSITI TEKNOLOGI MARA

FAKULTI KEJURUTERAAN KIMIA

INSTRUMENTAL LABORATORY

(CHE 515)

NAME : IHSAN SABRI BIN ROSLI

(2010562001)

MOHAMAD FADHLI BIN SAMSUDIN

(201077!")

MUHAMMAD JA#VIR B$ SULAIMAN

(20101"0!"") MUFIDAH BINTI MAHFU#

(201052!66!)

ROHA#IERAH BT CHE OMAR

(201012%%")

GROU& : EH221A

E'&ERIMENT :

DATE SUBMITTED : 21 NOVEMBER 2012

SEMESTER :

&ROGRAMMED CODE : EH 221

SUBMIT TO : DR KAMARIAH NOOR ISMAIL

T*+, A++-./*, M/3

(4)

M/3

A3*/.* 5

I*-.*- 5

T8,-9 5E;,


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$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$ $$$$

$$$$$$$$$$$$$$$$$$$$$$$$$$$

D/*, :

D/*, :

TABLE OF CONTENTS

TITLE PAGE

• Abstract 3

•

Introduction 4-5

• Theory 6-8

• Procedure 9

• Results !-"

• #iscussions 3-""

• $onclusions "3

• Re%erences "4

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ABSTRACT

The experiment was conducted to determine and draw the structure for unknown

compound A to I. The experiment for solid and liquid samples has almost the same

preparation’s way. The difference is only when for solid, it need to be dissolved first before

been transferred into N! tube. Then for both solid and liquid samples, three drops of a

deuterated solvent "usually chloroform# is added into the tube. Then, the tube is wrapped in a

tissue for paddin$ before inserted it into a holder of the centrifu$e. %pectral window is settin$

by modify the appearance and the spectrum is printed. &rom the analyses that have been

done, each unknown compound was determined. The I'(A) name for compound A is *, +

dimethylfuran-"* H #one, whereas compound is *methylcyclopentane/, -dione. Next,

compound ),0, and 1 are cyclohexane/,+dione, ethenyl "* E #but*enoate, and *

methylprop*enoate respectively. In addition, the analysis on compound & shows that it is

cyclobutylideneacetic acid, while compound 2 and compound 3 are "4methylfuran*yl#

methanol and hydroxy-methylcyclopent*en/one respectively. The last compound that

been analy5ed was compound I, that is hex*ynoic acid.

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INTRODUCTION

Nuclear ma$netic resonance spectroscopy "N!# is the technique to determinin$ the

structure of or$anic compounds. It is the only one for which a complete analysis and

interpretation of the entire spectrum is normally expected. 'nderstandin$ the physical

principle on which the methods are based is important to make sure it is success in usin$

N! as an analytical tool. The nuclei of many element isotopes have a characteristics spin.This includes /3 and /-) "but not /*)#. The N! behaviour of /3 and /-) nuclei has been

exploited by or$anic chemist since they provide valuable information that can be used to

deduce the structure of or$anic compounds. a$netic field will develop since a nucleus is a

char$ed particle in motion. /3 and /-) have nuclear spins of /6* and so they behave in a

similar fashion to a simple, tiny bar ma$net. 7hen a field is applied they line up parallel to

the applied field, either spin ali$ned or spin opposed but in the absence of a ma$netic field,

these are randomly oriented. Two schematic representations of these arran$ements are shown

below8

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There are two $eneral types of N! instrument which is continuous wave and

&ourier transform. 1arly experiments were conducted with continuous wave ").7.#

instruments, and in /9:; the first &ourier transform "&.T.# instruments is introduced.

)ontinuous wave N! spectrometer is in principle to optical spectrometer. The

sample is held in a stron$ ma$netic field, and the frequency of the source is slowly scanned.

The ma$nitude of the ener$y chan$es involved in N! spectroscopy is small. This means

that sensitivity is a ma because noise is random, it adds as the square root of the

number of spectra recorded. ecause of this, &ourier transform "&.T.# instruments became

available. In &TN!, all frequencies in a spectrum are irradiated simultaneously with a

radio frequency pulse. &ollowin$ the pulse, the nuclei return to thermal equilibrium. A time

domain emission si$nal is recorded by the instrument as the nuclei relax. A frequency domain

spectrum is obtained by &ourier transformation.

The N! instrumentation is shown as below>

&i$ure /8 basic arran$ement of an N! spectrometer

The sample is positions in the ma$netic field and excited via pulsations in the radio frequency

input circuit. The reali$ned ma$netic field induced a radio si$nal in the output circuit which

is used to $enerate the output si$nal. &ourier analysis of the complex output produces the

actual spectrum. The pulse is repeated as many times as necessary to be identified from the

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back$round noise. The pulse is actually a si$nal of frequency, F , is turned on and then off

a$ain very rapidly, then the result is an output consistin$ of many frequencies centred

about F with a bandwidth of /6t , where t is the duration of the pulse. This means that

radiation is produced of all frequencies in the ran$e F ? /6t . If t is very small, then a lar$e

ran$e of frequencies will be produced simultaneously, and all tar$et nuclei in a sample will be

excited.

THEORY

Basic principles of NMR

Nuclei with an odd mass or odd atomic number have @nuclear spin’. In the presence of

an applied external ma$netic field, /3 /-) nuclei exist in two nuclear spin states of different

ener$y. The difference in ener$y between the two spin states is dependent on the external

ma$netic field stren$th and is always small. . The spin states ener$y difference shown from

the equation below8

∆ E=γ h

2 π B

0

7here8 h (lanck’s constant; stren$th of external ma$netic field

$yroma$netic ratio, is the constant which is a property of the particularᵞ

nucleus

In the absence of a ma$netic field, these are randomly oriented but when a field is

applied they line up parallel to the applied field, either spin ali$ned or spin opposed. The

arran$ements of the spin orientation are shown below8

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&i$ure /8 %pin orientation

Chemical Shif

An N! spectrum is a plot of the radio frequency applied a$ainst absorption. A

si$nal in spectrum is known as resonance and frequency of si$nal is chemical shift. In other

word, chemical shift is defined as the frequency of the resonance expressed with reference to

a standard compound which is defined to be at ; ppm. The scale is in parts per million and it

is independent of the spectrometer frequency.

In an N! spectrum, a peak at a chemical shift of /; ppm is said to be downfield or

deshielded with respect to a peak at 4 ppm and the peak at 4 ppm is upfield or shielded with

respect to the peak at /; ppm.

There are several factors that may affect the chemical shift. This means that different types of proton will occur at different chemical shifts. The various factors include8

a! Elecrone"ai#i$ effec

The resonance position of protons bonded to carbon is shifted downfield by

electrone$ativity elements also bonded to the carbon. The electrone$ativity element

wtithdraws electron density from the carbon and its directly bonded protons which

diminished the ma$nitude of ma$netic field. Thus, the hi$her the electrone$ativity of

the directly bonded atom, the lar$er the downfield shift.

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&i$ure *8 The effect of electrone$ativity element on chemical shift

%! Ma"neic Anisorop$

Anisotropy means nonuniform. a$netic anisotropy means that there is a

nonuniform ma$netic field. 1lectron in systems such as aromatics, alkenes,

alkynes, carbonyl and others interact with the applied field which induced a ma$netic

field that causes the anisotropy. The effects of anisotropy are the nearby proton willexperience three fields which is the applied field, the shieldin$ field of the valence

electron and the field due to the system. Thus, shielded "smaller B# or deshielded

"lar$er B# and also ener$y required as well as the chan$es of frequency absorption are

depend on the position of the proton in the this third field. &i$ure - shows schematic

representation of anisotropy effect.

&i$ure - 8 Anisotropy effect

c! H$&ro"en Bon&in"

(rotons that are involved in hydro$en bondin$ usually C=3 and CN3 have a

lar$e ran$e of chemical shift values. The more hydro$en bondin$ there is, the more

protons are deshielded and the hi$her its chemical shift will be. 3owever, it is difficult

to predict since the amount of hydro$en bondin$ is susceptible to several factor such

as salvation, acidity, concentration and temperature.

'ROCEDURE

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Sample preparaion for li()i&

/. %ample liquid is transfer into the N! tube by usin$ lon$tipped (asteur pipette.

*. About three drop of a deuterated solvent "usually chloroform# is added into the tube.

-. Then, the tube is caped and spins in the hand centrifu$e to collect the residual sample

from the walls and collapse air pockets and bubbles.

+. The tube is wrapped in a tissue for paddin$ before inserted it into a holder of the

centrifu$e.

4. A thin strip of (arafilm around the seam between the tubes and its cap is wrapped to

prevent the sample from dryin$ out.

D. The tube is labeled.

Sample preparaion for soli&

/. A small amount of solid used is measured at the end of spatula. Then, sample solid is

put into a small test tube.

*. About three drop of a deuterated solvent "usually chloroform# is added into the tube.

Noted that the N! will N=T work if deuterated solvent is not usedE

-. The solid sample is dissolved and the solution is transferred into the N! tube.

+. The tube is caped and spins in the hand centrifu$e to collect the residual sample from

the walls and collapse air pockets and bubbles.

4. The tube is wrapped in a tissue for paddin$ before inserted it into a holder of the

centrifu$e.

D. A thin strip of (arafilm around the seam between the tubes and its cap is wrapped to

prevent the sample from dryin$ out.

:. The tube is labeled.

NMR Operain" 'roce&)re

/. Fock on the sample is obtained by ad


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*.* "-, s# • %at. alkanes , !3

/.+ "-,d# • %at. alkanes, !3

/-)

*;4.D • Getone, ! *)=

• Aldehydes, !)3=

/H9.H • 1ster, !)=*!’

/;-.4 • ! *))3*

H*.H • )=!

/D.9 • %at. alkane, !3

/D.- • %at. alkane, !3

/3

*.+ "+,t# • %at. alkane, !3

*.* "/,qrt# • %at. alkane, !3

/.4 "-,d# • %at. alkane, !3

/-)

/9+ • Getone, ! *)=

///.D • Aromatics

-;./ • ))=!

4.: • %at. alkane, !3

)

/3 *.: "H,t# • %at. alkane, !3

/-)

*;H.- • Getone, ! *)=

-:.D • ))=!

0

/3

:.+ "/,t# • Alkene, !)3)3!

:./ "/,qnt# • Alkene, !)3)3!

4.9 "/,d# • Alkene, !)3)3!

+.: "*,d# • 1ster, !)=*)3

/.9 "-,d# • %at. alkane, !3

/-)

/D-.* • 1ster, !)=*)3

/+: • ! *))3*

/+/.- • Alkene, !3))3!

/*/.: • Alkene, !3))3!

9:.+ • )=!

/H.* • %at. alkane

1 /3 :.- "/,t# • Alkene, !3))3!

D.; "*,s# • Alkene, !3))3!

+.: "*,d# • 1ster, !)=*)3

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*.; "-,s# • %at. alkane

/-)

/D+.- • 1ster, !)=*!’

/+/.4 • Alkene, !3))3!

/-4.4 • Alkene, !3))3! /*:.* • Alkene, ! *))3*

9:.H • )=!

/H.* • %at. alkane

&

/3

//.- "/,s# • )arboxylic acid, !)=*3

4.4 "/,s# • Alkene, !3))3!

*.4 "*,t# • %at. alkane

*.+ "*,t# • %at. alkane

*.; "*,qnt# • %at. alkane

/-)

/9- • )arboxylic acid, !)=*3

/;+.- • Alkene, ! *))3*

-*.- • %at. alkane

*/./ • %at. alkane

2

/3

D./ "/,d# • Alkene, !3))3!

4.9 "/,d# • Alkene, !3))3!

+.4 "*,s# • Alkene, ! *))3*

*.- "/,s# • Alcohol, !=3

*.- "-,s# • %at. alkane

/-

)

/4*.D • Alkene, !3))3!

/4*./ • Alkene, !3))3!

/;H.D • Alkene, !3))3!

/;D.- • Alkene, ! *))3*

4:./ • Alcohol, )=3

/-.4 • %at. alkane

3

/3

D.: "/,s# • Alkene, !3))3!

*.+ "*,t# • %at. alkane

*.- "*,t# • %at. alkane

*.; "-,s# • %at. alkane

/-) *;-.H • Getone, ! *)=

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/+9.4 • Alkene, ! *))3*

/+4.9 • Alkene, !3))3!

-*./ • )))

*:.- • %at. alkane/+.+ • %at. alkane

I

/3

9.: "/,s# • )arboxylic acid, !)=*3

*.- "*,t# • %at. alkane

/.D "*,sxt# • %at. alkane

/.; "-,t# • %at. alkane

/-)

/4H.4 • )arboxylic acid, !)=*3

9*.D • Alkyne

:*.9 • Alkyne

*/.; • %at. alkane

*;.: • %at. alkane

/-.+ • %at. alkane

DISCUSSION

7e are required to determine and draw a viable structure for compound A to I. &rom

the elemental composition and the relative molecular mass of the $iven compound, we can

determine the number of carbon, hydro$en and oxy$en present in the compounds. The

calculations involved are shown below8

1lemental composition8 ) C D+.-, 3 C *H.D, = C :.*

!elative molecular mass of the compounds8 //*./ $mol/

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!elative atomic mass8 ) C /*.;/$mol/, 3 C /.;/$mol/, = /D$mol/

Total /;;./

• Number of carbon, ) present is8

64.3

100.1×112.1gmol

−1=72.01 gmol

−1

72.01 gmol−1

12.01 gmol−1=6

• Number of hydro$en, 3 present is8

7.2

100.1×112.1gmol

−1=8.063gmol

−1

8.063gmol−1

1.01gmol−1 =7.98≈8

• Number of oxy$en, = present is8

28.6

100.1×112.1gmol

−1=32.028 gmol

−1

32.028 gmol−1

16 gmol−1

=2

3ence, from the above calculation, the molecular formula for the compounds to be

determined is )D3H=*

Compo)n& A the I'(A) name for this compound is *, +dimethylfuran-"* H #one

*

H NMR

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&

&

$'3

'

'

$'3

*+C NMR

&

&

$'3

'

'

$'3

The possible structure for compound A is *, +dimethylfuran-"* H #one. ased on the

data that had been $iven in experiment, we know that compound A has D peaks for ) and +

peak for 3. &or /-) N!, one of the chemical shifts that $iven in the experiment is *;4.D

ppm. &rom the table of chemical shift "refer above *;; ppm#, the functional $roup that

present is carbonyl $roup which is aldehyde and ketone. &or aldehyde, it must have /3 N!

chemical shift in the ran$e of 9 ppm to/; ppm whereas for ketone, it must have /3 N!

chemical shift in the ran$e of * ppm to - ppm. %o, it is proved that ketone present in the

compound A because the compound shows /3 N! chemical shift in the ran$e of * ppm to-

ppm. esides that, compound A must have double bond because it has chemical shift in the

ran$e of /;; ppm until *;; ppm, that is for /3 N!, the ran$e of chemical shift in the ran$e

of 4 ppm to D.4 ppm. ased on the structure above, it shown that ) that attached to the =

$roup ")=# will have hi$her chemical shift because the presence of stron$ electrone$ative

element that decrease the electron density.

Compo)n& B the I'(A) name for this compound is *methylcyclopentane/, -dione

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*H NMR

$'3

&&

*+C NMR

$'3

&&

&or compound , the possible structure is *methylcyclopentane/, -dione . &rom the

value $iven, we can identify the functional $roup for the compound. &rom the /-) N!

)hemical %hifts, it have δ

/9+.; "ketone 6 aldehyde#, ///.D "alkene#, -;./ "alkene# and 4.:

"alkanes#. Then, for /3 N! )hemical %hift, it have δ *.+ and *.* "ketone 6 alcohol#, and

/.4 "alkanes#. In this compound, it consists of several functional $roup include ketone,

cycloalkane. In /3 N!, for "+,t#, it has three peaks where it has two carbon "contain four

hydro$en# next to carbon that has two hydro$en. &or "/,qrt#, it has four peaks where it has

carbon "contain one hydro$en# next to carbon that has three hydro$en. Fastly "-, d#, it has

two peaks where it has carbon "contain three hydro$en# next to carbon that has one hydro$en.

-3 has lowest chemical shifts because in shielded area. /3 has hi$her chemical shift because

next to pi system and *3 has hi$hest chemical shift because hi$her in hydro$en bondin$ and

next to pi system.

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Compo)n& C the I'(A) name for this compound is cyclohexane/,+dione

*H NMR

&

&

*+C NMR

&

&

&or compound ), the possible structure is cyclohexane/, +dione. &rom the value

$iven, we can identify the functional $roup for the compound. &rom the /-) N! )hemical

%hifts, it have δ *;H.- "ketone 6 aldehyde# and -:.D "ketone 6 alkene 6 alkanes#. Then, for

/3 N! )hemical %hift, it has δ *.: "ketone#. &or this compound, it must have

symmetric compound which it has two peaks, so it has same value of chemical shift. In this

compound, the most accurate compound consists of ketone and cycloalkane functional $roup.

In /3 N!, for "H,t#, it means that each side contains two carbon where each carbon contain

two hydro$en.

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Compo)n& D the I'(A) name for this compound is ethenyl "* E #but*enoate

*H NMR

$'3 & $'"

&

*+C NMR

$'3 & $'"

&

&or compound 0, the possible structure is ethenyl "* E #but*enoate. &rom the value

$iven, we can identify the functional $roup for the compound. &rom the /-) N! )hemical

%hifts, it have δ /D-.* "ester 6 alkene#, /+:.; "alkene 6 aromatic#, /+/.- and /*/.: "alkene#,

9:.+ "aromatic# and /H.* "alkene 6 alkanes#. Then, for /3 N! )hemical %hift, it has δ

:.+ and :./ "aromatic#, 4.9 and +.: "alkene#, and /.9 "alcohol 6 alkene#. &or this compound, it

is a strai$ht chain carbon. It consists of some functional $roup include alkene, alkanes and

ester $roup. In /3 N!, it consist of "/,t#, means that it has three peak where it has carbon

"contain one hydro$en# next to carbon that has two hydro$en. &or "/,qnt#, it has five peaks

where it has carbon "contain one hydro$en# next to carbon that has four hydro$en. &or "/,d#,

it has two peaks where it has carbon "contain one hydro$en# next to carbon that has one

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hydro$en. &or "*,d#, it has two peaks where it has carbon "contain two hydro$en# next to

carbon that has one hydro$en. Then, for "-,d#, it has two peaks where it has carbon "contain

three hydro$en# next to carbon that has one hydro$en. "/3, t# has hi$hest chemical shift value

because located beside the electrone$ative element "=#.

Compo)n& E the I'(A) name for this compound is ethenyl *methylprop*enoate

*H NMR

$'" &$'3

&

$'"

*+C NMR

$'" &$'3

&

$'"

&or compound 1, the possible structure is ethenyl *methylprop*enoate. &rom the

value $iven, we can identify the functional $roup for the compound. &rom the /-) N!

)hemical %hifts, it have δ /D+.-, /+/.4, /-4.4, /*:.*, "alkene#, 9:.H "aromatic# and /H.*

"alkanes#. Then, for /3 N! )hemical %hift, it have δ :.- "aromatic#, D.; and +.:

"alkenes# and *.; "ketone 6 aldehyde 6 alkynes#. In this compound, it consists of some

functional $roup include ester $roup, alkenes, and cycloalkane. In/

3 N!, for "/,t#, it has

three peaks where it has carbon "contain one hydro$en# next to carbon that has two hydro$en.

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&or "*,s#, it has one peaks where it has carbon "contain two hydro$en# next to carbon that has

no hydro$en. Then, for "*,d#, it has two peaks where it has carbon "contain two hydro$en#

next to carbon that has one hydro$en. &or "-,s#, it has one peaks where it has carbon "contain

three hydro$en# next to carbon that has no hydro$en. It can see that "/3,t# has hi$hest

chemical shift value because of electrone$ative element "=# lower the electron density around

the 3 and ).

Compo)n& F the I'(A) name for this compound is cyclobutylideneacetic acid

*H NMR

&'

&

*+C NMR

&'

&

&or compound &, the possible structure is cyclobutylideneacetic acid. &rom the /-)

N! )hemical %hifts, it has δ /9-.; "ketone 6 aldehyde#, /;+.- "aromatic#, :;.; "ether

6alcohol#, -*.- "alkanes# and */./ "alkene 6 alkanes#. Then, for /3 N! )hemical %hift, it

have δ //.- "carboxylic acid#, 4.4 "alkenes#, *.4 and *.+ "ketone 6 alkynes#, and *.;

"alkenes 6 alkynes 6 ketone#. &or this compound, it is a strai$ht chain carbon. It consists of

several functional $roup include carboxyl acid, alkenes and alkanes. In /3 N!, for //.-

"/,s#, it refers to hydroxyl $roup. It has hi$hest chemical shift because located beside

electrone$ative element "=#. Then, for 4.4 "/,s#, it refers to the carbon that has one peak where a carbon "contain one hydro$en# next to carbon that has no hydro$en. &rom the

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compound, it can be seen at the alkenes $roup. &or "*,t#, it has three peaks where it has

carbon "contain two hydro$en# next to carbon that has two hydro$en and for "*,qnt#, it

has five peaks where it has carbon "contain two hydro$en# next to carbon that has four

hydro$en.

Compo)n& , the I'(A) name for this compound is "4methylfuran*yl# methanol

*H NMR

&

&'

$'3

*+C NMR

&

&'

$'3

&or compound 2, the possible structure is "4methylfuran*yl# methanol .&rom the

/3 N! and /-) N! data $iven, we know that this compound has D peaks for carbon, )

and 4 peaks for hydro$en, 3. The chemical shifts data for /-) N! that $iven to us is B

/4*.D, /4*./, /;H.D, /;D.-, 4:./ and /-.4. &rom the value $iven, we can identify the

functional $roup for the compound. &rom the data, B /4*.D and /4*./ must be nei$hborin$

carbon, and by referrin$ to the /-) N! chemical shifts table, the possible functional $roup

at these values is alkene "double bond#. B /;H.D and /;D also came from the nei$hborin$

carbon as their values are very close and the possible functional $roup at these values is also

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alkene. &or B4:./, the possible functional $roup is ether or alcohol. 7hereas, for B/-.4 is

saturated alkanes. The chemical shifts data for /3 N! $iven is B 4.9"/,d#, D./"/,d#, +.4"*,s#,

*.-"/,s# and *.-"-,s#. y referrin$ to the /3 N! chemical shifts table, the possible

functional $roup for B4.9"/,d# and D./"/,d# is alkene, for B+.4"*,s# is alcohol, esters or alkene.

Fastly, for B*.- is alcohol, ketones or alkyne "triple bond#. y comparin$ the information

$ained from both table, the similarities of the functional $roup they have is alkene and

alcohol, which means this compound must have this functional $roup. esides these *

functional $roups, we need one more functional $roup to complete the structure that has *

oxy$en atoms, so the most possible functional $roup is ether.

Compo)n& H the I'(A) name for this compound is *hydroxy-methylcyclopent*

en/one

*H NMR

&

&'

$'3

*+C NMR

&

&'

$'3

&or compound 3, the possible structure is *hydroxy-methylcyclopent*en/one.

&rom the /3 N! and /-) N! data $iven, we know that this compound has D peaks for

carbon, ) and + peaks for hydro$en, 3. The chemical shifts data for /-) N! that $iven to us

is B *;-.H, /+9.4, /+4.9, -*./, *:.- and /+.+. &rom the value $iven, we can identify the

functional $roup for the compound. &rom the data, B /+9.4 and /+4.9 must be nei$hborin$


at these values is alkene "double bond system#. B-*./ and *:.- also came from the

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nei$hborin$ carbon as their values are very close and the possible functional $roup at these

values is ketones, saturated alkane or alkene. &or B*;-.H, the possible functional $roup is

ketones or aldehydes. 7hereas, for B/+.+ is saturated alkanes. The chemical shifts data for /3

N! $iven is B *.;"-,s#, *.+"*,t#, D.:"/,s# and *.-"*,t#. y referrin$ to the /3 N! chemical

shifts table, the possible functional $roup for B*.+, *.-, *.; is alcohol, ketones or alkene, for

BD.+ is alkene. y comparin$ the information $ained from both table, the similarities of the

functional $roup they have is alkene, saturated alkanes or ketones which means this

compound must have this functional $roup. esides these functional $roups, we need one

more functional $roup to complete the structure that has * oxy$en atoms, so the most possible

functional $roup is alcohol.

Compo)n& I the I'(A) name for this compound is hex*ynoic acid

*H NMR

&' $'3

&

*+C NMR

&' $'3

&

&rom the /3 N! and /-) N! data $iven, we know that this compound has D peaks

for carbon, ) and + peaks for hydro$en, 3. The chemical shifts data for /-) N! that $iven

to us is B /4H.4, 9*.D, :*.9, */.;, *;.: and /-.+. &rom the value $iven, we can identify the

functional $roup for the compound. &rom the data, B */.; and *;.: must be nei$hborin$


at these values is alkene "double bond system# or saturated alkanes. &or B/4H.4, the possible

functional $roup is carboxylic acid. &or B9*.D is ether or alcohol. &or B:*.9, the possible

functional $roup is alcohol, ether, or alkyl "triple bond system#.7hereas, B/-.+ is alkene andsaturated alkane. The chemical shifts data for /3 N! $iven is B 9.:"/,s#, *.-"*,t#, /.D"*,sxt#

22


23/24

and /.;"-,t#. y referrin$ to the /3 N! chemical shifts table, the possible functional $roup

for B*.- and /.D is alcohol, ketones and alkyl, for B9.: is ketones and for B/.; is saturated

alkane. y comparin$ the information $ained from both table, the similarities of the

functional $roup they have is saturated alkanes, alcohol, ketones and alkyl $roup. ut instead

of alcohol and ketones $roup, the carboxylic acid is the most accurate to construct this

structure.

CONCLUSION

The experiment were successfully conducted where the entire unknown compound

were determined. &rom the analysis and investi$ation that have been done, it shows that the

I'(A) name for compound A to I are *, +dimethylfuran-"* H #one, *methylcyclopentane

/,-dione, cyclohexane/,+dione, ethenyl "* E #but*enoate, *methylprop*enoate,

cyclobutylideneacetic acid, "4methylfuran*yl# methanol, *hydroxy-methylcyclopent*

en/one, and hex*ynoic acid respectively.

The compound can be determined by analyses the peak and the chemical shifts shown

in the N! spectrum. The splittin$ number of peak was known by lookin$ at the proton

presents near the sin$le carbon. Fet say there are two nei$hborin$ hydro$en present at the

carbon, the number of peaks will be triplet.

0eterminin$ the chemical shifts of every structure of compound part is very important

as to know the compound. )hemical shifts are the frequency of a resonance si$nal influenced

by if the compound is shielded or deshielded. The shieldin$ effect in 3N! is influenced

by factors such as inductive effects by electrone$ative $roups, ma$net anisotropy, and

hydro$en bondin$. &rom all these knowled$e, it explains why the compounds A to I were

determined to be the compound that have been mentioned above. In conclusion, the

experiment was successfully conducted and the ob


24/24

REFERENCE

Boo-s

/. 2raham %., )rai$ ., "*;;:#.Organic chemistry." 9th edition#8 John 7iley K %on

*. Laboratory Manual CHE 515,&aculty of )hemical 1n$ineerin$

-. Notes NMR spectroscopy, &aculty of )hemical 1n$ineerin$

Inerne

/. Nuclear a$netic !esonance, Instrumentalion 0ecember //, *;/*. !etrieve from

http866teachin$.shu.ac.uk6hwb6chemistry6tutorials6molspec6nmr-.htm

*. Nuclear a$netic !esonance "N!# %pectroscopy. 0ecember /;, *;/*. !etrieve

from http866www.chem.ucal$ary.ca6courses6-4/6)arey4th6)h/-6ch/-nmr/.html

-. Nuclear a$netic !esonance %pectroscopy. 0ecember /;, *;/*. !etrieve from

http866www*.chemistry.msu.edu6faculty6reusch6LirtTxtJml6%pectrpy6nmr6nmr/.htm
http://teaching.shu.ac.uk/hwb/chemistry/tutorials/molspec/nmr3.htmhttp://www.chem.ucalgary.ca/courses/351/Carey5th/Ch13/ch13-nmr-1.htmlhttp://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/Spectrpy/nmr/nmr1.htmhttp://www.chem.ucalgary.ca/courses/351/Carey5th/Ch13/ch13-nmr-1.htmlhttp://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/Spectrpy/nmr/nmr1.htmhttp://teaching.shu.ac.uk/hwb/chemistry/tutorials/molspec/nmr3.htm

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