aromatic compounds Flashcards
what is the formula of benzene?
C6H6
what is the empirical formula of benzene?
CH
what is the state of benzene at room temperature?
liquid
what is the bond angle of benzene?
120
what are the 3 features of benzene that doesn’t support Kekule’s model?
- benzene is resistant to addition reactions (benzene doesn’t decolourise bromine water)
- enthalpy change of hydrogenation of benzene is more stable than predicted
- all the carbon bonds are the same length
what technique was used to find the bond lengths of benzene
x-ray diffraction
what happens to the 4th electron in the p-orbital of each carbon atom in benzene
- it delocalises to form rings of electron density above and below the hexagon
- forming rings of delocalised electron density above/below the hexagon
how do the rings of electron density affect the stability of benzene
- makes benzene very stable
- even though it is unsaturated (aromatic stability)
why does benzene have a relatively high melting point
close packing of flat hexagonal molecules when solid
is benzene soluble in water? explain why?
- no
- it is non-polar
dangers of benzene - why is it not used in school?
it is a carcinogen
how do you name compounds containing a benzene ring?
benzene or phenyl
why is benzene attacked by electrophiles?
high electron density above/below ring due to delocalised electrons
nitration of benzene is what type of reaction?
electrophilic substitution reaction
which ion is used to nitrate benzene?
NO2+
what is the catalyst in nitration of benzene
sulfuric acid
H2SO4
how is the electrophile NO2+ ion generated during the nitrification of benzene (conditions+equations)
- concentrated H2SO4 and concentrated HNO3
- 50°C
- overall: H2SO4 + HNO3 → HSO4- + NO2+ + H2O
how is the H2SO4 catalyst regenerated in the nitration of benzene
HSO4- + H+ → H2SO4
(H+ from benzene ring)
what type of catalyst is used for a Friedel-Crafts reaction?
a halogen carrier
e.g. AlCl3
why does benzene not react directly with halogens?
the aromatic ring is too stable
what is happening when AlCl4- is formed in terms of electrons?
the lone pair of electrons on the chlorine atom is forming a coordinate bond to Al
how is the AlCl3 catalyst formed?
AlCl4- + H+ → HCl + AlCl3
(H+ from benzene)
how could you use a Friedel-Crafts mechanism to add a methyl group to a benzene ring?
- use a halogenalkane
- add AlCl3 (catalyst)
- to create an electrophile that can attack the benzene
what reactions can you carry out to show the weak acidity of phenol?
- neutralisation reaction
- with NaOH
- but absent when you react phenol with carbonates
what is the relative ease of electrophilic substitution of phenol compared to benzene and why?
- it is easier for electrophilic substitution to occur with phenol
- because oxygen lone pair of electrons from the -OH group are partially delocalised into ring
- this increases the electron density of the ring
- electrophiles are more attracted to phenol
what is the directing effect of electron donating groups OH and NH2?
- group donates electrons onto ring, so electron density increases
- reactivity increases
- 2nd substitution at 2- or 4- positions
what is the directing effect of electron withdrawing group NO2?
- group withdraws electrons from ring
- reactivity decreases
- 2nd substitution at 3- position