medchem 14 Flashcards
the carbon in the carbolyxic acid is a —- which means its linked to — with the bond angle of — it also has a —-which can be protonated like alcohol and the carbon can be attacked by a —-
- triagonal carbon , 3 different atoms, 120
- carboxyl group ( COOH)
- nucleophile
the — between the particles increases the intermolecular attractions between particles are disrupted and — has to be provided to distrupt them
distance
energy as tempreture
the boiling point is — due to —- and its — soluble and they exists as h-bonded dimers in — state
- high (118 c )
- hydrogen bonding
- water
- liquid
— contains even number of carbons between — the chains are synthesised by —–
- fatty acids
- 12-20
- 2 carbon units
saturated fatty acids have —- and the linear chains can be —-
unsaturated fatty acids have —– and the bonds are usually in — configuration
- no double bonds and is saturated w/ hydrogen , rotatable
- at least one double bond
- cis
the omega refers to the position of c double bond c is always closest to — end as the oleic acids in —– fatty acids
methyl group
unsaturated fatty acids
double bonds will always be separated by at least one ethylene group (-ch2-) in —– fatty acids
polysatyrated fatty acids
( so w/ every double bond we’ll leave a space )
prostaglandins starts with —- in the membrane
phospholipids
the phospholipase A2 frees the —- from the membrane
arachidonic acid
— is a 20 carbon polyunsaturated fatty acid
arachdonic acid
arcahndoic is converted into — from which the prostogadins are sythesied
- PG2
(YOU SHOULD RECOGNIZE THE STRUCTURE OF PROSTOGLADIN CHECK SLIDE 13)
postagladin strcuture:
5-memebrerd ring , 20 carbon and COOH
the reactions of carbolyxic acid with bases produce —
as carbolyxic acid + NaOH –>
- salts
- sodium carboxylate and water
carbolyxic acids are — acids
weak
the dissociation aka ionisation of carbolyxic acid produce:
carbolyxic acid + h20 –> —-
- conjugate base and h30+
the Ka is —-
larger the value of Ka — the acid
product/ reactant so
[ conjugate base ] [ h30] / carbolyxic acid + h20
stronger
— is the acid ionisation or acid dissociation constant
Ka
which of these are the strong acid
A: ch3cooh and Ka of : 1.8 x 10 -5
B: clch2cooh and Ka os: 1.4 x 10-3
B
Ka values are cumbersome to remember so — is used instead the they have —- relationship
- pKa = -log Ka or ( log 1/ka)
- inverse
stronger acid has — Ka and — pka
- large
- small
the reason why carbolyxic acid are stronger acids than alcohols:
because of the conjugate base
the carbolixic acids conjugate base is stabilised by resonance so its formed easily while the aloxide isn’t
carboxylate anions are stabilised by — because the -ve charge is spread over —
resonance , 2 oxygens ( check the structure of resonance in slide 21 )
is there resonance stabilised in aloxide ion?
NO
another proof of resonance stabilisation is the —
carbon to oxygen bonds are different one is c=o and one is c-o ( that’s in methanoic acid )
while the conjugate base of it aka the sodium methanoate they are both identical both between single and double bond
In RCOOH , the substituent R influences the — of the cooh group so it could be either — or —
acidity
electron donating or withdrawing
( CHECK SLIDE 24 )
—- reduces the -ve charge and make the conjugate base more stable so its easily formed and makes carbolyxic acid more strong
- electron withdrawing group as nitro groups since its pka is low
—- destabilise the conjugate base and makes the acid weaker
electron donating group as methyl groups since their pka is high
we can synthesises carbolyxic acid and the oxidation of primary alcohol or aldehydes by using —-
KMn04 , a strong oxidising agent , potassium permengate
or we could use: grind reagent with —
in grinard reagent the C-Mg bond is —
grinared reagents react with co2 to give —
- co2 ( rx+ mg aka alkyl halid ) —> and we use dry ether as a catalyst to produce RMGX ( the gernard reagent )
- polar
- carbokyxic acid
oxidation of alkyl benzene with KMN04 gives and the alkyl benzene can be —– but not —–
benzoic acid
methyl, primary, secondary , not teritry
