Why does benzene undergo electrophilic substitution reactions easily and nucleophilic substitutions with difficulty?

1 Answer

Answer :

Ans. Due to the presence of an electron cloud containing 6 pi electrons above and below the plane of the ring, benzene is a source of electrons. Consequently, it attracts the electrophiles towards it and repels nucleophiles. As a result, benzene undergoes electrophilic substitution reactions easily and nucleophilic substitution with difficulty.

Related questions

Description : Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions? (a) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. (b) ... adds to an aldehyde, neither H− nor R− can be eliminated since they are strongly basic

Last Answer : Once the nucleophile adds to an aldehyde, neither H− nor R− can be eliminated since they are strongly basic

Description : Alkyl halides undergo (a) Electrophilic substitution reactions (b) Electrophilic addition reactions (c) Nucleophilic substitution reactions (d) Nucleophilic addition reactions

Last Answer : Nucleophilic substitution reactions

Description : Out of benzene, m–dinitrobenzene and toluene which will undergo nitration most easily and why?

Last Answer : Ans. -CH3 group is electron donating while –NO2 group is electron withdrawing. Therefore, maximum electron density will be in toluene, followed by benzene and at least in m-dinitrobenzene. Therefore, the ease of nitration decreases in the order: Toluene> benzene> m-dinitrobenzene

Description : Benzene reacts with concentrated HNO3 in the presence of concentrated H2SO4 to give nitrobenzene. This reaction is an example of (a) Electrophilic addition (b) Nucleophilic addition (c) Electrophilic substitution (d) Nucleophilic substitution

Last Answer : Electrophilic substitution

Description : Benzene reacts with concentrated HNO3 in the presence of concentrated H2SO4 to give nitrobenzene. This reaction is an example of (a) Electrophilic addition (b) Nucleophilic addition (c) Electrophilic substitution (d) Nucleophilic substitution

Last Answer : Electrophilic substitution

Description : Which of the following characterizes the reactions of aldehydes and ketones? (a) electrophilic addition (b) electrophilic substitution (c) nucleophilic acyl substitution (d) nucleophilic addition; free radical addition

Last Answer : nucleophilic addition; free radical addition

Description : Which of the reactions between the following pairs of reagents proceeds by a mechanism that may be described as an electrophilic substitution? (a) Benzene + Br2/FeBr3 (b) Propene + Br2 (c) Acetone + NH2NH2 (d) Ethyl bromide + aq KOH

Last Answer : Benzene + Br2/FeBr3

Description : Esters and amides are most easily made by nucleophilic acyl substitution reactions on : (a) acid anhydrides (b) carboxylates (c) carboxylic acids (d) acid chlorides

Last Answer : acid chlorides

Description : The characteristic reaction of carboxylic acids is : (a) electrophilic addition (b) electrophilic substitution (c) nucleophilic addition (d) nucleophilic substitution

Last Answer : nucleophilic substitution

Description : Acetone reacts with HCN to form a cyanohydrin. It is an example of (a) Electrophilic addition (b) Electrophilic substitution (c) Nucleophilic addition (d) Nucleophilic substitution

Last Answer : Nucleophilic addition

Description : Propene reacts with bromine to form 1,2-dibromopropane. This is an example of (a) Nucleophilic addition (b) Electrophilic addition (c) Nucleophilic substitution (d) Electrophilic substitution

Last Answer : Electrophilic addition

Description : The chlorination of methane to give CCl4 is an example of (a) an electrophilic addition (b) a free-radical substitution (c) a nucleophilic addition (d) an electrophilic substitution

Last Answer : a free-radical substitution

Description : How an — OH group attached to carbon in the benzene ring activates benzene towards electrophilic substitution ?

Last Answer : The lone pair of electrons present on oxygen atom enter into resonance with the benzene ring. As a result, the electron density becomes higher at o- and p- position and due to higher electron density, the ring gets activated towards electrophilic substitution.

Description : What purpose does FeCl3 serve in the electrophilic aromatic substitution reaction between chlorine and benzene? (a) It serves as a radical initiator to produce the chlorine radical needed to propagate the ... by reacting with the Cl2 and thereby activates it toward attack by benzene's π electrons.

Last Answer : It serves as a Lewis acid catalyst by reacting with the Cl2 and thereby activates it toward attack by benzene’s π electrons.

Description : Which of the following is not a correct statement about the electrophilic substitution mechanism of benzene? (a) Benzene functions as a nucleophile. (b) Formation of a carbocation intermediate is the ... hybridized carbon in the ring. (d) The addition product is a frequently observed minor product.

Last Answer : The addition product is a frequently observed minor product.

Description : Which of the following can undergo nucleophilic substitution under ordinary conditions? I Allyl chloride II Benzyl chloride III n-Propyl chloride IV V

Last Answer : Which of the following can undergo nucleophilic substitution under ordinary conditions? I Allyl chloride II ... are correct D. I and III are correct

Description : Phenol is more reactive than benzene towards electrophilic substitution reaction. In case of Phenol, the intermediate carbocation is more resonance st

Last Answer : Phenol is more reactive than benzene towards electrophilic substitution reaction. In case of Phenol, the ... D. A is incorrect but R is correct

Description : Anthracene undergoes electrophilic substitution reactions mainly at (a) C-1 (b) C-2 (c) C-9 (d) C-1 and C-2

Last Answer : C-9

Description : Which of the following compounds reacts least rapidly in electrophilic substitution reactions? (a) Nitrobenzene (b) Phenol (c) Bromobenzene (d) Toluene

Last Answer : Nitrobenzene

Description : In electrophilic aromatic substitution reactions a chlorine substituent __________. (a) is a deactivator and a m-director (b) is a deactivator and an o,p-director (c) is an activator and a m-director (d) is an activator and an o,p-director

Last Answer : is a deactivator and an o,p-director

Description : Esters can be formed by nucleophilic substitution reactions of : (a) carboxylic acids and alcohols ; acid-catalyzed (b) acid chlorides and alcohols (c) both of the above (d) neither of the above

Last Answer : both of the above

Description : Which of the following statements correctly describes the general reactivity of alkynes? (a) An alkyne is an electron-rich molecule and therefore reacts as a nucleophile. (b) The σ bonds ... fail to undergo electrophilic addition reactions. (d) Alkynes are generally more reactive than alkenes.

Last Answer : Alkynes are generally more reactive than alkenes.

Description : Benzene cannot undergo – (1) Substitution (2) Addition (3) Elimination (4) Oxidation

Last Answer : (3) Elimination Explanation: Benzene can not undergo Elimination reaction.

Description : Benzene cannot undergo : (1) Substitution (2) Addition (3) Elimination (4) Oxidation

Last Answer : Elimination

Description : Explain why nucleophilic substitution reactions are not very common in phenols.

Last Answer : Explain why nucleophilic substitution reactions are not very common in phenols.

Description : (A) Ethyl chloride is more reactive than vinyl chloride towards nucleophilic substitution reactions. (R) Vinyl chloride is `+I` electron pushing group

Last Answer : (A) Ethyl chloride is more reactive than vinyl chloride towards nucleophilic substitution reactions. (R) Vinyl ... A) is incorrect but (R) is correct.

Description : Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds:

Last Answer : Identify the correct order of reactivity in electrophilic substitution reactions of the following ... C. `IIgtIgtIIIgtIV` D. `IIgtIIIgtIgtIV`

Description : Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds :

Last Answer : Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds : ... ` C. `2gt1gt3gt4` D. `2gt3gt1gt4`

Description : Which statement about the carbonyl group of ketones and aldehydes is true? I. It can attract nucleophiles. II. It can attract electrophiles. III. It tends to undergo addition reactions. IV. It tends to undergo substitution reactions. (a) I and III (b) II and IV (c) I, II, and III (d) I, III, and IV

Last Answer : I, II, and III

Description : Which of the following is not correct concerning substitution and elimination reactions of alkyl halides? (a) The electrophile replaces the leaving group. (b) Compounds containing electron-donating groups bonded to an ... replaced by another atom or group in substitution reactions. (d) (a) and (b)

Last Answer : (a) and (b)

Description : Assertion: Phenol is more reactive than benzene towards electrophilic reactions. Reason : The +R effect of OH group increases the electron density on

Last Answer : Assertion: Phenol is more reactive than benzene towards electrophilic reactions. Reason : The +R effect of ... D. A is incorrect but R is correct

Description : Benzene undergoes substitution reaction more easily than addition reaction because (a) it has a cyclic structure (b) it has three double bonds (c) it has six hydrogen atoms (d) there is delocalization of electrons

Last Answer : there is delocalization of electrons

Description : Benzene undergoes substitution reaction more easily than addition reaction because (a) it has a cyclic structure (b) it has three double bonds (c) it has six hydrogen atoms (d) there is delocalization of electrons

Last Answer : there is delocalization of electrons

Description : An organic compound (A) has a molecular weight 78 and an empirical formula CH. (A) is resistant to attack by oxidizing agents but undergoes substitution and addition reactions. X-ray analysis shows that the ... suggests that compound (A) is (a) Benzene (b) Cyclohexane (c) Toluene (d) n-Hexane

Last Answer : Benzene

Description : An organic compound (A) has a molecular weight 78 and an empirical formula CH. (A) is resistant to attack by oxidizing agents but undergoes substitution and addition reactions. X-ray analysis shows that the ... suggests that compound (A) is (a) Benzene (b) Cyclohexane (c) Toluene (d) n-Hexane

Last Answer : Benzene

Description : Out of benzene, m–dinitrobenzene and toluene which will undergo nitration most easily and why?

Last Answer : Ans. -CH3 group is electron donating while –NO2 group is electron withdrawing. Therefore, maximum electron density will be in toluene , followed by benzene and at least in m-dinitrobenzene. Therefore, the ease of nitration decreases in the order: Toluene> benzene> m-dinitrobenzene

Description : Phenol is an ortho-para director because the hydroxyl group : (a) donates electrons that increase electron density at ortho and para positions favoring nucleophilic attack. (b) donates ... para positions and attracts electrons away from meta positions favoring electrophilic attack on the ring.

Last Answer : donates electrons that increase electron density at ortho and para positions favoring electrophilic attack.

Description : Although benzene is highly unsaturated, it does not undergo addition reactions, why?

Last Answer : Ans. Because of extra stability, due to delocalization of π-electrons.

Description : Give reason: Alkanes undergo only substitution reactions but alkenes and alkynes undergo both substitution and addition reactions.

Last Answer : Alkenes and alkynes have double and triple bonds, which on breaking can add hydrogen atoms to satisfy the valency.

Description : 0.3780g of organic chloro compound gave 0.5740g of silver chloride in carius estimation .Calculate the percentage of chlorine present in the compound.

Last Answer : % of chlorine = 35.5*mass of AgCl formed * 100/143.5 * mass of the substance = 35.5*0.5740*100/143.5*0.3780 = 19.6 %

Description : In an estimation of sulphur by carius method 0.468 g of an organic compound gave 0.668 g of barium sulphate. Find the percentage of sulphur in the compound.

Last Answer : Mass of the compound = 0.468 g Mass of the barium sulphate = 0.668 g % of sulphur = 32 X Mass of barium sulphate X 100/ 233 X Mass of the compound = 32 x 0.668x100/ 233 x0.468 = 19.60 %

Description : An organic compound contain 69% carbon and 4.8% hydrogen, the remaining being oxygen. Calculate the masses of carbon dioxide and water produced when 0.20g of this substance is subjected to complete combustion.

Last Answer : Calculation of mass of CO2 produced: Mass of compound =0.20g %C =12 x C 69=12*mass of CO2 formed*100/44*0.2 Mass of CO2 formed =69*44*.2/12*100 = 0.506g Similarly, % H =2* mass of H2Oformed*100/18* ... compound 4.8=2* mass of H2Oformed*100/18* 0.2 Mass of H2Oformed =4.8*18*0.2/2*100 =0.0864g

Description : 0.257g of organic substance was heated with conc. sulphuric acid and then distilled with excess of strong alkali .the ammonia gas evolved was absorbed in 50ml of .1M HCl which required 23.2ml of c for neutralization at the end of the process. Determine the % of nitrogen in the compound ?

Last Answer : A. Vol of 0 .1M HCl taken = 50ml Vol of .1MNaOH used for neutralization of unused acid=23.2ml Now, 23.2 ml of .1MNaOH =23.2ml of .1MHCl Vol of .1MHCl unused=23.2ml Vol of .1MHCl required ... NH3 solution contain nitrogen = 14*26.8/10*1000 Percentage of Nitrogen=14*26.8*100/10*1000*.257 =14.6%

Description : Why freshly prepared FeSO4 is used in nitrogen testing ?

Last Answer : Because FeSO4 gets hydrolysed if its solution is stored for long.

Description : What is the principle of Dumas method for the estimation of N in the organic compound?

Last Answer : In Dumas method , Nitrogen present in organic compound on heating with CuO release free nitrogen gas ,which collected by the downword displacement of KOH. From the voiume of nitrogen gas collected at STP, Nitrogen could be estimated.

Description : Name the technique used to separate water from carbon tetrachloride?

Last Answer : Water and carbon tetrachloride could be separated using a separating funnel, since the two are immiscible and heavier carbon tetrachloride forms the lower layer.

Description : It is advisable to prepare Lassaignes extract in distilled water why?

Last Answer : Tap water usually contain dissolved chlorine which gives test for halogen.

Description : Name a decolorizing agent commonly used to decolorize the organic compound?

Last Answer : Activated Charcoal.

Description : What is the common criteria for purifying organic compound ?

Last Answer : Their Fixed Melting and Boiling point.

Description : Why Glycerol could not be prepared by steam distillation?

Last Answer : Glycerol decompose at its Boiling point.