Download - Reaction of Acyl Chloride and Anhydride
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Reaction of acyl
chloride and anhydrideNor Awaathif Bt Mohd Ghazali Lee
D20091035070
Sharifah Maizura Kasmawati SyedHamzah
D20091035071
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REACTION
INDUCTIONSET
EMPOWERING
ENHANCING
CLOSURE
STORY TELLING ON THE SPOT
ENJOYWATCHING
CROSSWORD
WIN AND
FORTUNE
MATCHTHEM
ACID
ANHYDRIDE
ACYL CHLORIDE
IUPACNAMENTRODUCTION
FUNCTIONALGROUPEACTION
WATER
ALCOHOL
PRIMARY
AMINE
INTRODUCTION
IUPACNAMEFUNCTIONALGROUP
REACTION
WATER
ALCOHOL
PRIMARY
AMINE
ACYLCHLORIDEACIDANHYDRIDE
Answer
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Far away in a jungle, there live a bearnamed Acid Anhydride. She lives therewith her mother and her little brother.Her mother was a widowed.
STORY TELLING
TIME
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One day, she decided to go for a walkwith her friend, Beez.. Suddenly, she
heard someone screaming..
Beez..do you hear that? she asked
curiously. Beez nodded his head.
Suspiciously, they walked forward tosee the thing that screamed justnow.
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Hello..what happened to you? AcidAnhydride asked politely.
I think I am lost now
Ouh..My name is Acid Anhydride. You cancall me Ann. This is my friend, Beez.
My name is Acyl Chloride. Just call meChlo. Nice to meet both of you. Could youplease help me to figure out the way out?
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Yeah..we can help you. But the dayis getting late now. Why not you juststay a night at my home first.Tomorrow we will figure out it.
After thinking for a while, Chlo willingto stay at Anns house for a night.
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At home, Anns mother Mrs Carboxylic Acidserved a very delicious food. Her brother,
Water was just sitting. By that time, theystarted to know each other.
The more they talked, the more similarities
between them. Ann did show her fatherpicture to Chlo. To make a suprise, theirfather is the same person which is MrCarboxylic Acid.
How this could happen? Could you pleasehelp Chlo and Ann to clear up the messes?
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Confused?? Let we arranged the
history of Chlos and Anns family.
Mr. Carboxylic Acid
Mrs. Carboxylic
Acid
Acid Anhydride Water
?
Acyl Chloride
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So what is the relationship
between Ann and Chlo?
The truth is, Mr. Carboxylic Acid
was married to Miss Chlorineafter divorced with Mrs
Carboxylic Acid. Later, they gotAcyl Chloride. So they are step
brother and sister.
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ON THE SPOT?
Carboxylic Acid
WaterAcyl ChlorideChlorineCarboxylic Acid
Acid Anhydride Carboxylic Acid
Rearrange the boxes so that it can become an equation of chemistry
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ASPIRIN VIDEO
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ACYL CHLORIDE ACID ANHYDRIDE
Polar Molecule Van Der Waals Dispersion Forces
Dipole-dipole Attraction Dipole-dipole Attraction
Van Der Waals Dispersion Forces Did not form Hydrogen Bond
Cannot form Hydrogen Bond (RO)O
ROCl -
WHAT ARE THEIR
CHARACTERISTIC?
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What is acyl chloride???
Actually acyl chloride is the product of
carboxylic acid which is for example ethanoicacid whichat theOH group we must
replaced by the chorine atom...
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However, it doesnt form hydrogen bonds and
acyl chlorides can not be said to dissolve in water
because they react (often violently) with it.
Is polar molecule, and also has dipole-dipole
attractions between its molecules as well as van
der Waals dispersion forces.
Like to know something
more about acyl
chloride????
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What is acyl anhydride???
Actually acyl anhydride is the product of
two carboxcylic acid which are ethanoic acidwhich at OH group and we need to remove a
molecule of water between them....
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Has both van der Waals dispersion forces and
dipole-dipole attractions
However it doesn't form hydrogen bonds. That
means that its boiling point isn't as high as a
carboxylic acid of similar size
More interesting facts
about acyl anhydride
are..
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Have an alkyl (or aromatic) group attached to a
carbonyl function plus a labile (easily displaced)
chlorine.
Acid chlorides can be shown in text
as: ROCl
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Acid anhydrides are formed when water is
removed from a carboxylic acid, hence the name.
Acid anhydrides can be shown in text as:
(RO)O
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The easiest way of thinking
about the names is to see the
relationship with thecorresponding carboxylic acid
Carboxylic Acid
Name
Acyl Chloride Name Acyl Chloride
Formula
Ethanoic Acid Ethanoyl Chloride CH3COCl
Propanoic Acid Propanoyl Chloride CH3CH2COCl
Butanoic Acid Butanoyl Chloride CH3CH2CH2COCl
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Need some exmple??
Here we go.
1. Said that we have something substituted into
the hydrocarbon chain2. Then the carbon in the -COCl group counts
as the number 1 carbon.
3. So the name is 2-methylbutanoyl chloride
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Try something special by naming it
with unique name
1. Take the name of the parent acid, and replace
the word "acid" by "anhydride".
2. "Anhydride" simply means "without water".3. So . . . ethanoic acid forms ethanoic anhydride(
propanoic acid forms propanoic anhydride,
and so on).
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CHCOCl + HO CHCOOH + HCl
What will happens when acyl
chloride reacts with water????
The products is..
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CHCOCl + CHCHOH
CHCOOCHCH + HCl
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Who can guess????...What is the
product when acyl chloride reacts
with primary amine????
CHCOCl + 2CHNH
CHCONHCH + CHNH+Cl
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The product when acyl
anhydride reacts with
alcohol is
(CHCO)O + CHCHOH 2CHCOOH
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Think.think. Think
The product when acyl
anhydride reacts withprimary amine is..
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A C Y L A N H E D I R O L H C L Y C A D
S H A S P I R I N F E V E R C I L I N K
A C A R B O X Y L I C A C I D P Y X H R
G H G E R R S A D H G Y C A T L Z Y Y I
P O Q T Y E U F A V Q Y P J O Z X V D V
O C U S F S B J M J P U F H T H G I R B
N O Z E J T U B E C H L O R I N Z D I T
I L F U Z I T R E Q J C K X F D H X D R
F A Z E T H A N O Y L C H L O R I D E O
I T K C K H N Y P A P J E T H A N O S U
C E A C N M O N F D Q P O L A R X K Z B
B U T A N O I C A N H Y D R I D E I I L
A V R U V Z C Y U N J V T E X R I K B E
T D Z S X C A S I R U W Q V S T R I V S
I B V R D E C R N Z S C X O Z E B V B T
O C T E T S I C O O H C L S M I K H K R
N D C O H P D C S M L O V E P O N C O U
E S T E S M S N S E L I H P O E L C U N
D S I A I A C I D G A S E O U S A D I C
G L O B A L W A R M I N G W W S H D A T
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Lets Brainwash Your Mind!!Just find all the answers for all the questionsbelow in the crossword puzzle provided. It canbe diagonal, backward, straight, vertical,horizontal and etc. Good Luck!
1. __________ is more reactive compared to anester and an amide.2. One of carboxylic acid derivatives.3. What product will be produced between thereaction of salicyclic acid and aceticanhydride?
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4. Name of the structure
5. An acyl chloride like ________ is a colorlessfuming liquid.
6. Acyl chlorides can be used to preparecarboxylic acid derivatives including acidanhydrides, ester and amides by reactingacid chlorides with a salt of carboxylic acid,an __________, or an amine respectively.
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7. _________ is often used as an analgesic to
relieve minor aches and pains, as anantipyretic to reduce fever and as an anti-inflammatory medication.8. Amide, ester and anhydride are derivatives
of _________.9. _________ have an alkyl (or aromatic) groupattached to a carbonyl function plus alabile(easily displaced) chlorine.10.Acyl chlorides highly reactive entities arehighly susceptible to attack by __________.
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REACTANT
CH3COCl + H2O
(CH3CO)2O + CH3CH2OH
CH3COCl + CH3CH2OH
CH3COCl + 2CH3NH2
PRODUCT
CH3COOH + HCl
CH3CONHCH3 + CH3NH3+Cl-
2CH3COOH
CH3COOCH2CH3 + HCl
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WIN AND FORTUNE
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TYPE OF FORCES
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FUNCTIONAL GROUP
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NAME OF ACID
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TYPE OF ACYL CHLORIDE
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SUBSTITUTION
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Acyl Chloride
Introduction
at theOHgroup at
carboxylicacid replacedby the chorine
atom
Physicalproperties
Funtionalgroup
ROCl
IUPACname
Example:EthanoylChloride
Reaction
Water
Alcohol
Primary
amine
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Acyl anhydride
Introduction
remove a molecule ofwater between -OH
group at twocarboxylic acid
Physicalproperties
Funtional group
(RO)2O
IUPAC name
replace the word"acid" by
"anhydride".EXAMPLE:ethanoicacid forms ethanoic
anhydride
Reactions
Water
Alcohol
Primary amine
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Answer
Cross
word
Match
them
WIN AND
FORTUNE
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A C Y L A N H E D I R O L H C L Y C A D
S H A S P I R I N F E V E R C I L I N K
A C A R B O X Y L I C A C I D P Y X H R
G H G E R R S A D H G Y C A T L Z Y Y I
P O Q T Y E U F A V Q Y P J O Z X V D V
O C U S F S B J M J P U F H T H G I R B
N O Z E J T U B E C H L O R I N Z D I T
I L F U Z I T R E Q J C K X F D H X D R
F A Z E T H A N O Y L C H L O R I D E O
I T K C K H N Y P A P J E T H A N O S U
C E A C N M O N F D Q P O L A R X K Z B
B U T A N O I C A N H Y D R I D E I I L
A V R U V Z C Y U N J V T E X R I K B E
T D Z S X C A S I R U W Q V S T R I V S
I B V R D E C R N Z S C X O Z E B V B T
O C T E T S I C O O H C L S M I K H K R
N D C O H P D C S M L O V E P O N C O U
E S T E S M S N S E L I H P O E L C U N
D S I A I A C I D G A S E O U S A D I C
G L O B A L W A R M I N G W W S H D A T
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REACTANT PRODUCT
CHCOCl + HO CHCOOH + HCl
(CHCO)O + CHCHOH CHCO(NH)CH +
CHNH+Cl
CHCOCl + CHCHOH 2CHCOOH
CHCOCl+ 2CHNH CHCOOCHCH + HCl
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1.Type of forces ~ Van Der Waals Forces
2.Functional Group ~ Carbonyl
3.Name of Acid ~ Acid Anhydride4.Type of Acyl Chloride ~ Propanoyl Chloride
5.Substitution ~ Nucleophilic Substitution