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