Reaction of acyl chloride and anhydride

Nor Awaathif Bt Mohd Ghazali Lee D20091035070 Sharifah Maizura Kasmawati Syed Hamzah D20091035071

ACYL CHLORIDE

STORY TELLING
ACID ANHYDRIDE

ON THE SPOT

CLOSURE

INDUCTION SET
REACTION

ENJOY WATCHING

Answer

EMPOWERING

ENHANCING

ACID ANHYDRIDE
FUNCTIONAL GROUP

INTRODUCTION

ACYL CHLORIDE
CROSS WORD
INTRODUCTION

IUPAC NAME

IUPAC NAME
FUNCTIONAL GROUP

REACTION

MATCH THEM

REACTION

WIN AND FORTUNE

WATER ALCOHOL PRIMARY AMINE

WATER ALCOHOL PRIMARY AMINE

STORY TELLING TIME

Far away in a jungle, there live a bear named Acid Anhydride. She lives there with her mother and her little brother. Her mother was a widowed.

One day, she decided to go for a walk with her friend, Beez.. Suddenly, she heard someone screaming..
Beez..do you hear that? she asked curiously. Beez nodded his head. Suspiciously, they walked forward to see the thing that screamed just now.

Hello..what happened to you? Acid Anhydride asked politely.

I think I am lost now Ouh..My name is Acid Anhydride. You can call me Ann. This is my friend, Beez. My name is Acyl Chloride. Just call me Chlo. Nice to meet both of you. Could you please help me to figure out the way out?

Yeah..we can help you. But the day is getting late now. Why not you just stay a night at my home first. Tomorrow we will figure out it. After thinking for a while, Chlo willing to stay at Anns house for a night.

At home, Anns mother Mrs Carboxylic Acid served a very delicious food. Her brother, Water was just sitting. By that time, they started to know each other. The more they talked, the more similarities between them. Ann did show her father picture to Chlo. To make a suprise, their father is the same person which is Mr Carboxylic Acid. How this could happen? Could you please help Chlo and Ann to clear up the messes?

Confused?? Let we arranged the history of Chlos and Anns family.

Mr. Carboxylic Acid

Mrs. Carboxylic Acid

Acid Anhydride

Water

Acyl Chloride

So what is the relationship between Ann and Chlo? The truth is, Mr. Carboxylic Acid was married to Miss Chlorine after divorced with Mrs Carboxylic Acid. Later, they got Acyl Chloride. So they are step brother and sister.

ON THE SPOT?
Acid Anhydride Carboxylic Acid

Carboxylic Acid

Carboxylic Acid

Chlorine

Acyl Chloride

Water

Rearrange the boxes so that it can become an equation of chemistry

ASPIRIN VIDEO

WHAT ARE THEIR CHARACTERISTIC?

ACYL CHLORIDE
Polar Molecule

ACID ANHYDRIDE
Van Der Waals Dispersion Forces

Dipole-dipole Attraction
Van Der Waals Dispersion Forces

Dipole-dipole Attraction
Did not form Hydrogen Bond

Cannot form Hydrogen Bond

ROCl

(RO)O
-

What is acyl chloride??? Actually acyl chloride is the product of carboxylic acid which is for example ethanoic acid which at the OH group we must replaced by the chorine atom...

Like to know something more about acyl chloride???? Is polar molecule, and also has dipole-dipole attractions between its molecules as well as van der Waals dispersion forces. However, it doesnt form hydrogen bonds and acyl chlorides can not be said to dissolve in water because they react (often violently) with it.

What is acyl anhydride??? Actually acyl anhydride is the product of two carboxcylic acid which are ethanoic acid which at OH group and we need to remove a molecule of water between them....

More interesting facts about acyl anhydride are..

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

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

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

The easiest way of thinking about the names is to see the relationship with the corresponding carboxylic acid

Carboxylic Acid Name

Ethanoic Acid Propanoic Acid

Acyl Chloride Name Acyl Chloride Formula

Ethanoyl Chloride Propanoyl Chloride Butanoyl Chloride CH3COCl CH3CH2COCl CH3CH2CH2COCl

Butanoic Acid

Need some exmple?? Here we go.

1. Said that we have something substituted into the hydrocarbon chain 2. Then the carbon in the -COCl group counts as the number 1 carbon. 3. So the name is 2-methylbutanoyl chloride

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).

What will happens when acyl chloride reacts with water???? The products is..

CHCOCl + HO

CHCOOH + HCl

CHCOCl + CHCHOH

CHCOOCHCH + HCl

Who can guess????...What is the product when acyl chloride reacts with primary amine????
CHCOCl + 2CHNH

CHCONHCH + CHNH+Cl

(CHCO)O + H0

2CHCOOH

The product when acyl anhydride reacts with alcohol is

(CHCO)O + CHCHOH

2CHCOOH

Think.think. Think The product when acyl anhydride reacts with primary amine is..

A S A G P O N I F I C B A T I O N

C H C H O C O L A T E U V D B C D

Y A A G Q U Z F Z K A T R Z V T C

L S R E T S E U E C C A U S R E O

A P B R Y F J Z T K N N V X D T H

N I O R E S T I H H M O Z C E S P

H R X S U B U T A N O I C A C I D

E I Y A F J B R N Y N C Y S R C C

D N L D A M E E O P F A U I N O S

I F I H V J C Q Y A D N N R Z O M

R E C G Q P H J L P Q H J U S H L

O V A Y Y U L C C J P Y V W C C O

L E C C P F O K H E O D T Q X L V

H R I A J H R X L T L R E V O S E

C C D T O T I F O H A I X S Z M P

L I P L Z H N D R A R D R T E I O

Y L Y Z X G Z H I N X E I R B K N

C I X Y V I D X D O K I K I V H C

A N H Y D R I D E S Z I B V B K O

D K R I V B T R O U B L E S T R U

E
D G

S
S L

T
I O

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A B

S
I A

M
A L

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C W

N
I A

S
D R

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G M

L
A I

I
S N

H
E G

P
O W

O
U W

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S S

L
A H

C
D D

U
I A

N
C T

Lets Brainwash Your Mind!! Just find all the answers for all the questions below in the crossword puzzle provided. It can be diagonal, backward, straight, vertical, horizontal and etc. Good Luck! 1. __________ is more reactive compared to an ester and an amide. 2. One of carboxylic acid derivatives. 3. What product will be produced between the reaction of salicyclic acid and acetic anhydride?

4. Name of the structure

5. An acyl chloride like ________ is a colorless fuming liquid. 6. Acyl chlorides can be used to prepare carboxylic acid derivatives including acid anhydrides, ester and amides by reacting acid chlorides with a salt of carboxylic acid, an __________, or an amine respectively.

7. _________ is often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever and as an antiinflammatory medication. 8. Amide, ester and anhydride are derivatives of _________. 9. _________ have an alkyl (or aromatic) group attached to a carbonyl function plus alabile (easily displaced) chlorine. 10.Acyl chlorides highly reactive entities are highly susceptible to attack by __________.

REACTANT
CH3COCl + H2O

PRODUCT
CH3COOH + HCl CH3CONHCH3 + CH3NH3+Cl-

(CH3CO)2O + CH3CH2OH

CH3COCl + CH3CH2OH

2CH3COOH

CH3COCl + 2CH3NH2

CH3COOCH2CH3 + HCl

WIN AND FORTUNE

TYPE OF FORCES

FUNCTIONAL GROUP

NAME OF ACID

TYPE OF ACYL CHLORIDE

SUBSTITUTION

Acyl Chloride

Introduction

Funtional group

Reaction IUPAC name Water Primary amine

Physical properties

at the OH group at carboxylic acid replaced by the chorine atom

Alcohol
ROCl

Example: Ethanoyl Chloride

Acyl anhydride
Introduction Funtional group IUPAC name Reactions

remove a molecule of water between -OH group at two carboxylic acid

(RO)2O

Water replace the word "acid" by "anhydride". EXAMPLE:ethanoic acid forms ethanoic anhydride

Alcohol

Physical properties
Primary amine

Cross word

Answer
WIN AND FORTUNE Match them

A S A

C H C

Y A A

L S R

A P B

N I O

H R X

E I Y

D N L

I F I

R E C

O V A

L E C

H R I

C C D

L I P

Y L Y

C I X

A N H

D K R

G
P O N I F I C B A T I O N E D G

H
O C O L A T E U V D B C D S S L

G
Q U Z F Z K A T R Z V T C T I O

E
T S E U E C C A U S R E O E A B

R
Y F J Z T K N N V X D T H S I A

R
E S T I H H M O Z C E S P M A L

S
U B U T A N O I C A C I D S C W

A
F J B R N Y N C Y S R C C N I A

D
A M E E O P F A U I N O S S D R

H
V J C Q Y A D N N R Z O M E G M

G
Q P H J L P Q H J U S H L L A I

Y
Y U L C C J P Y V W C C O I S N

C
P F O K H E O D T Q X L V H E G

A
J H R X L T L R E V O S E P O W

T
O T I F O H A I X S Z M P O U W

L
Z H N D R A R D R T E I O E S S

Z
X G Z H I N X E I R B K N L A H

Y
V I D X D O K I K I V H C C D D

Y
D R I D E S Z I B V B K O U I A

I
V B T R O U B L E S T R U N C T

REACTANT

PRODUCT

CHCOCl + HO

CHCOOH + HCl

(CHCO)O + CHCHOH

CHCO(NH)CH + CHNH+Cl

CHCOCl + CHCHOH

2CHCOOH

CHCOCl + 2CHNH

CHCOOCHCH + HCl

1.Type of forces ~ Van Der Waals Forces 2.Functional Group ~ Carbonyl 3.Name of Acid ~ Acid Anhydride 4.Type of Acyl Chloride ~ Propanoyl Chloride 5.Substitution ~ Nucleophilic Substitution