Why do alkenes prefer to undergo electrophilic addition reaction while arenes prefer electrophilic substitution reaction? Explain.
Due to the presence of a π -electron cloud above and below the plane of alkenes and arenes, these are electron rich molecules and, therefore, provide sites for the attack of electrophiles. Hence, they undergo electrophilic reactions. Alkenes undergo electrophilic addition reactions because they are unsaturated molecules. For example,
Arenes, on the other hand, cannot undergo electrophilic addition reactions. This is because benzene has a large resonance energy of 150.4 kJ mol-1. During electrophilic addition reactions, two new σ-bonds are formed but the aromatic character of benzene gets destroyed and, therefore, resonance energy of benzene ring is lost. Hence, electrophilic addition reactions of arenes are not energetically favourable. Arenes, in contrast, undergo electrophilic substitution reactions in which σ C – H bond is broken and new σ C – X bond is formed: The aromatic character of benzene ring is not destroyed and benzene retains its resonance energy. Hence, arenes undergo electrophilic substitution reactions.
In the alkane, CH3CH2—C(CH3)2—CH2—CH(CH3)2, identify 1 °, 2 °, 3 ° carbon atoms and give the number of H-atoms bonded to each one of these.
Nucleophiles and electrophiles are reaction intermediates having electron rich and electron deficient centres respectively. Hence, they tend to attack electron deficient and electron rich centres respectively. Classify the following species as electrophiles and nucleophiles.
Which of the following are correct?
(a) CH3 – O – CH+2 is more stable than CH3 – CH+2
(b) (CH3)2CH+ is less stable than CH3 – CH2 – CH+2
(c) CH2 = CH – CH+2 is more stable than CH3 – CH2 – CH+2
(d) CH2 = CH+ is more stable than CH3 – CH+2
Out of benzene, m-dinitrobenzene and toluene which will undergo nitration most easily and why?
For the following compounds, write structural formulas and IUPAC names for all possible isomers having the number of double or triple bond as indicated:
(a) C4H8 (one double bond) (b) C5H8 (one triple bond)
Arrange the following set of compounds in order of their decreasing relative reactivity with an electrophile, E+.
(a) Chlorobenzene, 2, 4-dinitrochlorobenzene, p-nitrochlorobenzene
(b) Toluene,p—H3C—C6H4—NO2, p—O2N—C6H4—NO2.
Arrange the following: HCl, HBr, HI, HF in order of decreasing reactivity towards alkenes.
Why does the presence of a nitro group-make the benzene ring less reactive in comparison to the unsubstituted benzene ring? Explain.
Rotation around carbon-carbon single bond of ethane is not completely free. Justify the statement.
Draw the cis- and trans-structures for hex-2-ene. Which iosmer will have higher b.p. and why?
Arrange benzene, n-hexane and ethyne in decreasing order of acidic behaviour. Also give reason for this behaviour.
Which are the correct IUPAC names of the following compound
(a) 5-(2′,2′-Dimethylpropyl)decane
(b) 4-Butyl-2,2-dimethylnonane
(c) 2,2-Dimethyl-4-pentyloctane
(d) 5-neo-Pentyldecane
Write chemical equations for the combustion reaction of the following hydrocarbons, (i) Butane (ii) Pentene (iii) Hexyne (iv) Toluene
Write the IUPAC names of the following compounds.
(i) (CH3)CCH2C(CH3)3 (ii) (CH3)2C(C2H5)2
Arrange the following carbanions in order of their decreasing stability.
(A) H3C-C ≡ C–
(B) H-C ≡ C–
(C) H3C – CH–2
(a) A>B>C
(b) B>A>C
(c) C>B>A
(d) C>A>B
Alkynes on reduction with sodium in liquid ammonia form trans alkenes. Will butene formed on the reduction of but-2-yne show geometrical isomerism?
Why does benzene undergo electrophilic substitution reactions easily and nucleophilic substitutions with difficulty?
Arrange the following alkyl halides in decreasing order of the rate of β -elimination reaction with alcoholic KOH.
In an electrophilic substitution reaction of nitrobenzene, the presence of nitro group ________ ‘
(a) deactivates the ring by inductive effect
(b) activates the ring by inductive effect
(c) decreases the charge density at ortho- and para-positions of the ring relative to meta-position by resonance
(d) increases the charge density at meta-position relative to the ortho and para-positions of the ring by resonance
The intermediate carbocation formed in the reactions of HI, HBr and HC1 with propene is the same and the bond energy of HCl, HBr and HI is 430.5 kJ mol-1,363.7 kJ mol–1 and 296.8 kJ mol-1 What will be the other of reactivity of these halogen acids?
(a) What effect the branching of an alkane has on its melting point?
(b) Which of the following has highest boiling point?
(i) 2-methyl pentane
(ii) 2, 3-diethyl butane
(iii) 2, 2-dimethyl butane
Discuss the preparation of alkanes by Wurtz reaction. What is the limitaHon of the reaction?
How will you demonstrate that double bonds of benzene are somewhat different from that of olefins?
Write the structure and IUPAC names of different structural isomers of alkenes corresponding to C5H10.
The molecules having dipole moment are________ .
(a) 2,2-Dimethylpropane
(b) trans-Pent-2-ene
(c) cw-Hex-3-ene
(d) 2,2,3,3-Tetramethylbutane
Arrange the following set of compounds in the order of their decreasing . relative reactivity with an electrophile. Give reason.
