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Taichi Quan
muhtelif konular melekler – cinler ve daveti, divan edebiyatinda melekler ve cinler, cebrail:, mikail:, israfil:, azrail:, azazil (seytan):, harut ve marut:, ridvan:, kiramen katibin:, da’vet-na...
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ChemistryFull description
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drum
EtikFull description
kkk
Descripción: drum
organic
The carbonyl group he carbonyl group !"#$%& group !"#$%& is the functional group found in co'pounds such as aldehydes aldehydes(( ketones(( and carboxylic acids. ketones acids.
In aldehydes aldehydes the the carbonyl group is at the end of the carbon chain and so has at least one hydrogen attached to it.
In ketones ketones the the carbonyl group is in the 'iddle of a carbon chain and so has two alkyl groups attached groups attached to it.
Representing aldehydes and ketones *ldehydes and ketones *ldehydes ketones cannot be be distinguished distinguished by their their 'olecular for'ula because they ha+e the sa'e functional group. ,hat is the 'olecular for'ula of the aldehyd aldehyde e and ketone below-
an aldehyde Both ha+e the 'olecular for'ula C3H6O
a ketone
Representing aldehydes and ketones *ldehydes and ketones *ldehydes ketones are therefore represented represented either either using displayed displayed or or structural formulae. formulae.
CH3CHO
CH3COCH2CH3
CH3CH2CH2CHO
CH3CH2COCH2CH3
Naming aldehydes *ldehydes are na'ed using *ldehydes using the suffi suffi al ( and follow the sa'e con+entions as for na'ing alkanes.
ethanal
propanal
2methylbutanal
Naming ketones etones are na'ed using the suffi one.
propanone
hexan3one
Like alkenes( ketones ketones with four or 'ore carbon ato's display positional isomerism because isomerism because the carbonyl group 'ay appear between different carbon ato's. In these cases( a nu'ber is used before the one to indicate the first carbon in+ol+ed.
Naming aldehydes and ketones acti!ity
"ynthesis of aldehydes and ketones
#roperties of aldehydes and ketones he carbonyl group is polar due to the greater electronegati+ity electronegati+ity of oygen !3.)& than carbon !2./&. his influences the properties of aldehydes and ketones( such as solubility. 5'all aldehydes and ketones are soluble in water due to hydrogen bonding between a lone pair on the oygen of the carbonyl group and the hydrogen of the water. *s si6e increases( solubili solubility ty decreases due to interference in hydrogen bonding by the hydrocarbon 7tails of the aldehydes9ketones.
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&oiling points' a comparison
&oiling points and intermolecular forces he general increase in boiling points fro' alkanes to aldehydes9ketones and alcohols is due to the inter'olecular forces between each type of 'olecule.
(lkanes are only held together by +an der ,aals forces. (lkanes are hese forces increase with the si6e9length of a 'olecule.
he polar carbonyl group in aldehydes aldehydes and and ketones ketones 'eans 'eans that as well as +an der ,aals forces( these 'olecules are also held together by dipoledipole interactions.
(lcohols are held together by +an der ,aals forces and (lcohols are dipoledipole interactions. In addition( these 'olecules can for' hydrogen bonds with each other( due to the slightly positi+e hydrogen ato' of the hydroyl group.
Reacti!ity of the carbonyl group *lthough double bonds bonds re:uire 'ore energy energy to break than than single bonds( co'pounds with double bonds tend to be 'ore reacti+e as addition reactions reactions are possible possible.. 5o'e of the che'ical properties of aldehydes and ketones result fro' the polar nature of the #$% bond.
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he positi+e charge on the carbon ato' 'akes it open to attack by nucleophiles nucleophiles..
*ldehydes and ketones *ldehydes ketones can be reduced reduced(( for'ing pri'ary and secondary alcohols respecti+ely.
*ldehydes *ldehyde s 'ay also be oxidi)ed oxidi)ed to to carboylic acids.
Nucleophilic addition using cyanide
*angers of HCN ;ydrogen cyanide !;#<& is highly +olatile li:uid !boiling point 2/ =#&( which has a faint bitter al'ond s'ell. In solution( hydrogen cyanide partially dissociates> HCN+a,-
H%+a,- % CN+a,-
;ydrogen cyanide is highly toic because it inhibits a 'itochondrial en6y'e that is essential for respiration. Being so +olatile and fla''able( it is difficult to handle safely. * safer alternati+e alternati+e is potassiu' potassiu' cyanide( cyanide( which is is a solid at roo' te'perature and is therefore easier to handle. *n *n acidified solution contains both the ; ? and #<@ ions.
Reduction of aldehydes and ketones
*istinguishing aldehydes . ketones
*etecting a carbonyl group
Reactions of aldehydes and ketones
(ldehydes and ketones' true or false/
Carboxylic acids Carboxylic acids ha+e acids ha+e a carboxyl group !@#%%;& consisting of a carbonyl group and a hydroyl group attached to the ter'inal carbonyl carbon. #arboylic acids are na'ed using the suffi oic acid . ethanoic acid is the si'plest carboylic acid and is found in bee and ant stings. Athanoic acid is the acid that gi+es +inegar its sharp taste and s'ell. It is also i'portant in the che'ical industry and about /. 'illion tonnes are used worldwide each year
Naming carboxylic acids
&oiling points of carboxylic acids
"ynthesis of carboxylic acids
Oxidation of 01 alcohols and aldehydes #arboylic acids can be created by the oidation of aldehydes by oidi6ing agents such as potassiu' dichro'ate!CI&.
hey can also be created by the oidation of pri'ary alcohols( again using potassiu' dichro'ate!CI&.
Hydrolysis Hydroly sis of nitriles #arboylic acids can also be prepared by the hydrolysis of nitriles.. nitriles
he nitrile is reflued with water and hydrochloric acid. he carboylic acid can then be distilled fro' the reaction 'iture.
Reacti!ity of carboxylic acids he reacti+ity of carboylic acids results( in part( fro' the polari6ation of its bonds.
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%$he reactions of carboylic acids include>
neutralisation the carboylic acid loses a proton to neutralisation for' a carboyl carboylate ate salt
nucleophilic substitution substitution the positi+ely@charged carbon is attacked by a nucleophile( resulting in substitution of the %; group
esterification esterification reaction with an alcohol to for' an ester.
orming the carboxylate ion #arboylic acids are weak acids and partially dissociate in a:ueous solution>
carboxylate ion he negati+e charge is delocali6ed across the carboylate group( resulting in a 'ore stable ion. he delocali6ation is represented by adding a second dotted line to the carbon oygen bonds( which are both e:ui+alent.
Reactions ith carbonates #arboylic acids are the only organic co'pounds that are strong enough acids to react with either sodiu' carbonate or sodiu' hydrogencarbonate. Deaction of ethanoic acid and sodiu' carbonate> 2CH3COOH % Na2CO3 4 2CH3COONa % CO2 % H2O sodium ethanoate
Deaction of 'ethanoic acid and sodiu' hydrogencarbonate> HCOOH % NaHCO3 4 HCOONa % CO2 % H2O sodium methanoate
he for'ation of bubbles of carbon dioide gas 'akes these reactions useful as a test for carboylic acids.
Reactions ith alkalis #arboylic acids will react with alkalis( such as sodiu' hydroide( in a neutrali6ation reaction> RCOOH % NaOH 4 RCOONa % H2O Deaction of propanoic acid and sodiu' hydroide> CH3CH2COOH % NaOH 4 CH3CH2COONa % H2O sodium propanoate
Deaction of butanoic acid and potassiu' hydroide> CH3CH2CH2COOH % 5OH 4 CH3CH2CH2COO5 % H2O potassium butanoate
Carboxylic acids' a summary
lossary
7hat8s the keyord/
9ultiplechoice ,ui)
7hat are esters/ :sters are carboxylic acid deri+ati+es :sters are acid deri+ati+es with the hydrogen of the hydroyl group replaced by an alkyl group !hydrocarbon group !hydrocarbon chain& or an aryl group !an group !an aro'atic ring&.
ethyl ethanoate +contains an alkyl group-
methyl ben)oate +contains an aryl group-
:sterification
Naming esters he na'es of esters are based on the carboylic acid and alcohol fro' which they are produced. he first co'ponent of this ester na'e( the methyl methyl(( is deri+ed fro' the alcohol methanol methanol.. methylethanoate methyl ethanoate
he second co'ponent of the na'e( the ethanoate ethanoate(( is deri+ed fro' the carboylic acid ethanoic acid. acid.
ethylmethanoate ethyl methanoate
propylethanoate propyl ethanoate
ethanol ? ethanol ? 'ethanoic acid
propanol ? propanol ? ethanoic acid
Naming esters
Hydrolysis Hydroly sis of esters
;ses of esters 5horter chain esters ha+e fruity s'ells and tastes( which 'akes the' useful as sol+ents in perfu'es and fla+ourings.
Eor ea'ple( ethyl butanoate s'ells of pineappleF pentyl ethanoate s'ells of pears( and octyl ethanoate s'ells of oranges.
Asters are used as artificial fragrances and fla+ours as synthesi6ing the ester is often cheaper than etraction fro' the natural source.
;ses of esters Asters are also useful as glues( such as those used for constructing plastic 'odel aircraft kits( and as plastici6ers plastici6e rs to increase the fleibility of plastics. Asters ha+e low boiling points and e+aporate readily. his 'akes the' useful as industrial sol+ents( for ea'ple in paints. Athyl ethanoate is one such co''on sol+ent( being used in the decaffeination of tea( as well as a laboratory sol+ent for chro'atography.
:sters in fats and oils
Naming fatty acids Eatty acids ha+e syste'atic na'es as well as co''on na'es. Eor ea'ple( the syste'atic na'e for oleic acid is octadec@4@ enoic acid. 5o'e co''on fatty acids are eplained below. Common name
saturated( used for 'aking soaps 'onounsaturated( found in 'ost fats and oli+e oil polyunsaturated( found in +egetable oils
"aturated and unsaturated
:sters' true or false/
Trans fats
and health
ost naturally occurring iso'ers of unsaturated fatty acids are the cis for'( such as cis@octadec@4@enoic acid( found in oli+e oil( a+ocados a+ocados and nuts.
In the partial hydrogenation of +egetable oils( the trans for' of the fatty acid( such as trans@octadec@4@enoic acid( 'ay be for'ed.
* diet high in in trans fats fats(( along with saturated fats( can lead to an increased risk of coronary heart disease +CH*-. +CH*-.
Cholesterol and lipoproteins Cholesterol is a lipid that regulates Cholesterol is fluidity in cell 'e'branes. It is transported in lipoproteins lipoproteins..
9aking soap and biodiesel
7hat is acylation/ (cylation is the process in which an acyl group !D#%& (cylation is group !D#%& is introduced to another 'olecule by an acylating agent. agent. (cid deri!ati!es contain deri!ati!es contain an acyl group( and are deri+ed fro' carboylic acids. hey ha+e the general for'ula D#% and include esters( acid chlorides and acid anhydrides.
= group
Name of acid deri!ati!e
eneral formula
:xample
%D
ester
D#%%D
ethyl ethanoate( #;3#%%#2;.
#l
acid chloride
D#%#l
ethanoyl chloride( #;3#%#l
%#%D
acid anhydride
D#%%#%D
ethanoic anhydride( #;3#%%#%#;3
(cylation *cid deri+ati+es deri+ati+es are i'portant acylating acylating agents agents due to their polari6ed carbonyl group. he carbonyl group is attacked by nucleophiles at the #δ?( replacing . he speed of acylation depends on>
the reacti+ity of the nucleophile( according to its ability to donate its lone pair to t o an electron@de electron@deficient ficient carbon
the electron@releasing electron@releasing or attracting power of ( which affects the 'agnitude of the ? charge on the carbonyl carbon
how easily is lost.
7hat are acid chlorides/ (cid chlorides( chlorides( also known as acyl chlorides( contain a chlorine ato' attached to the acyl group. *cid chlorides chlorides are na'ed na'ed with the suffi suffi oyl F the ter' chloride is also added.
ethanoyl chloride
propanoyl chloride
7hat are acid anhydrides/ (cid anhydrides are anhydrides are prepared by the reaction of two 'olecules of a carboylic acid( resulting in the eli'ination of a 'olecule of water.
Naming acid anhydrides he acyl group is na'ed after the carboylic acid with the suffi oic F the ter' anhydride is also added.
ethanoic anhydride
propanoic anhydride
*cid anhydrides anhydrides can only be na'ed na'ed in this way when they are sy''etrical. 5o'e unsy''etrical acid anhydrides are known but they are less co''on.
:ster> acid chloride or acid anhydride/
Naming acyl compounds
Reacti!ity of acid chlorides he oygen and chloride ato's attached to the acyl carbon are groups that both withdraw electron density.
δ – δ+ δ –
*s a result( result( the carbonoygen carbonoygen and carbonchlorine carbonchlorine bonds are both polar( with a δ? charge on the carbon ato'. his 'eans the acyl carbon ato' is susceptible to attack by nucleophiles nucleophiles(( resulting in substitution of the chloride.
Reacti!ity of acid anhydrides Both the oygen ato's attached to the acyl carbon withdraw electron density. *s a result the carbonoygen carbonoygen bonds are polar( with δ? charges on both the acyl carbon ato's.
δ – δ+ δ – δ+ δ –
his 'eans the acyl carbon ato's are susceptible to attack by nucleophiles( resulting in substitution of a carboylate ion.
The addition?elimination mechanism
(cid chloride reactions
Relati!e reacti!ity of nucleophiles a''onia y t i + i t c a e r g n i s a e r c n i
J
a'ide
a'ine
J
<@substituted a'ide
alcohol
J
ester
water
J
carboylic acid
Relati!e reacti!ity of nucleophiles
(pplications of acylation reactions In organic synthesis reactions( the use of acid anhydride is fa+oured o+er the corresponding acid chloride for se+eral reasons> acid chlorides !e.g. ethanoyl chloride&
difficult to handle as they react +ery readily with water so need to be used in water@free conditions
react to produce corrosi+e ;#l.
acid anhydrides !e.g. ethanoic anhydride&
cheaper to produce
not as 'oisture sensiti+e
less corrosi+e
produce carboylic acids( which are safer than ;#l.
