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1. Draw the complete electron pushing mechanism for reaction that you are performing. For the substitution step, identify the nucleophile, electrophile, and leaving group.
2. Why is it important to mix the 2-naphthol and sodium hydroxide prior to adding 1- bromobutane? What might happen is you were to mix 2-naphthol, NaOH, and bromobutane all simultaneously?
3. Compare the acidity of 2-naphthol and ethanol. Which is more acidic? Why?
ANSWER ALL OR DONT ANSWER, I KNOW THE RULES DONT EXPLAIN IT TO ME.
Explanation / Answer
Mechanism of substitution reaction:
A)SN2 rection:Nucleophilic sunstitition second order reaction:
R-X + Y- (One slow step) -------> [ Y-1/2----R----X-1/2 ] -----> R-Y + X-
T.S.
SN1 rection:Nucleophilic sunstitition first order reaction:
R-X Step-I ---------> [ Y----R----X- ] ------> R+ Y- Step-II -------> R-Y + X-
[ i ] Carbocation
X = Nucleophile leaving group
Y = Incoming nucleophile
B)Electrophilic substitution reaction:
Ar + E+ ..Slow step ......> [Ar(H)NO2]+ Fast step ----> Ar-NO2 + H+
[I] Wheland Intermediate
E = Electrophile H + : Leaving electrophile
& is incoming electrophile NO2
2) It is necessary to mix. 2-naphthol with NaOH because naphthoate anion is more reactive (It has real charge on oxygen ) than unionised 2-naphthol (formal charge on oxygen ). Hence the rate of the reaction is faster with 1-bromobutane.
If all reactants are added at the same time then 1-bromo butane can under go hydrolysis & yield of the substitution reaction of 1-bromobutane gets lowered with 2-naphthol. The product mixture is formed.
3) In 2-Naphthol OH group is bonded with SP2 hybridized aryl group having more ' s ' characters ,hence it is more electron with drawing. Naphthoxide anion formed is stabilised by resonance because of conjugation with aryl rings .This offers greater acidity to OH group, shifting equilibrium to the right liberatinh H+ ions.
In ethanol OH is bonded to SP3 hybrized carbon atom which is having less ' s 'characrers & alkoxide anion is not stabilised by resonance in absence of conjugation with double bond.
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