Aryl halides are extremely less reactive towards nucleophilic substitution. Predict and explain the order of reactivity of the following compounds towards nucleophilic substitution:
After the attachment of the nucleophile at the carbon carrying -Cl, the intermediate compound is stabilised due to resonance. Due to electron withdrawing nature of-NO2, the nucleophile is easily attached to the benzene ring. Greater the number of -NO2 groups in the molecule, greater will be the ease with which the nucleophile will be attached. Hence, the order of reactivity is III > II > I.
Match the structures of compounds given in Column I with the classes of compounds given in Column II.
How will you bring about the following conversions?
(i)Ethanol to but-l-yne . (ii)Ethane to bromoethene
(iii)Propene to 1-nitropropane (iv)Toluene to benzyl alcohol
(v)Propene to propyne (vi)Ethanol to ethyl fluoride
(vii)Bromomethane to propanone (viii)But-l-ene to but-2-ene
(ix)1-Chlorobutane to n-octane (x)Benzene to biphenyl
Elimination reactions (especially Beta-elimination) are as common as the nucleophilic substitution reaction in case of alkyl halides. Specify the reagents used in both cases.
Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl3. Which of the following species attacks the benzene ring in this reaction?
(a) CP (b) Cl+ (c) AlCl3 (d) [AlCl4]–
Alkyl halides are prepared from alcohol by treating with
(a) HCl + ZnCl2 (b) RedP + Br2
(c) H2SO4 + KI (d) all the above
Which of the following compounds will give racemic mixture on nucleophilic substitution by OH ion?
Ethylene chloride and ethylidene chloride are isomers. Identify the correct statements.
(a) Both the compounds form same product on treatment with alcoholic KOH
(b) Both the compounds from same product on treatment with aqueous NaOH
(c) Both the compounds form same product on reduction
(d) Both the compounds are optically active
Which of the following are secondary bromides?
(a) (CH3),CHBr (b) (CH3)3C CH2Br
(c) CH3CH(Br)CH2CH3 (d) (CH3)2CBrCH2CH3
What are the IUPAC name of the insecticide DDT and benzenehexachloride?
Why is their use banned in India and other countries?
Diphenyls are potential threat to the environment. How are these produced from arylhalides?
Which of the following statements are correct about the reaction intermediate?
(a) Intermediate (iii) is unstable because in this carbon is attached to 5 atoms.
(b) Intermediate (iii) is unstable because carbon atom is sp2 hybridised.
(c) Intermediate (iii) is stable because carbon atom is sp2 hybridised.
(d) Intermediate (iii) is less stable than the reactant (ii).
Which compound in each of the following-pairs . will react faster in SN2 reaction with -OH? (i)CH3Br or CH3I
(ii)(CH3)3CCl or CH3Cl
Write the structures and names of the compounds formed when compound ‘A' with molecular formula, C7H8 is treated with Cl2 in the presence of FeCl3.
Some alkylhalides undergo substitution whereas some undergo elimination reaction on treatment with bases. Discuss the structural features of alkyl halides with the help of examples which are responsible for this difference.
Benzene < Chlorobenzene < Dichlorobenzene < Bromochlorobenzene Arrange the following compounds in increasing order of their boiling points
Assertion (A): KCN reacts with methyl chloride to give methyl isocyanide Reason (R): CN– is an ambident nucleophile.
Assertion (A): Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene.
Reason (R): N02 group is a w-directing group.
Which of the following compounds can be classified as aryl halides ? (a) p-ClC6H4CH2CH(CH3)2 (b) p-CH3CHCl(C6H4)CH2CH3 (c) o-BrH2CC6H4CH(CH3)CH2CH3 (d) C6H5Cl
Compound (A) with molecular formula C4H9Br is treated with aq. KOH solution. The rate of this reaction depends upon the concentration of the compound A' only. When another optically active isomer B' of this compound was treated with aq. KOH solution, the rate of reaction was found to be dependent on concentration of compound and KOH both.
(i) Write down the structural formula of both compounds A' and B'.
(ii) Out of these two compounds, which one will be converted to the product with inverted configuration.
Discuss the nature of C – X bond in the haloarenes.
C – X bond in haloarenes is extremely less reactive towards nucleophilic
Write structures of the following compounds:
(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcydohexane
(iii) 4-tert. Butyl-3-iodoheptane
(iv) 1,4-Dibromobut-2-ene
(v) 1-Bromo-4-sec. butyl-2-methylbenzene.
In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?
In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?
Write the equations for the preparation of 1-iodoobutanefrom (i)1-butanol (ii)1-chlorobutane (iii) but-l-ene.
Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b) Compound (b) is reacted, with HBr to give (c) which is an isomer of (a). When (a) is reacted with sodium metal it give compound (d), C8H18 which is different from the compound formed when n-butyl bromide is reacted with sodium. Give the structural formula of (a) and write the equations for all the reactions.
Which of the compounds will react faster in SN1 reaction with the –OH ion?
CH3 – CH2 – Cl or C6H5 – CH2 – Cl
Predict the major product formed when HCl is added to isobutylene. Explain the mechanism involved.
Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium? Give reason for your answer.
In the following questions, a statement of Assertion (A) followed by a statement of Reason (R) is given. Choose the correct option out of the choices given below each question:
(a)Assertion and Reason both are correct and Reason is the correct explanation of Assertion.
(b)Assertion and Reason both are wrong.
(c)Assertion is correct but Reason is wrong.
(d)Assertion is wrong but Reason is correct.
(e)Assertion and Reason both are correct statements but Reason is not the correct explanation of Assertion.
Assertion (A): Phosphorus chlorides (tri and penta) are preferred over thionyl chloride for the preparation of alkyl chlorides from alcohols.
Reason (R): Phosphorus chlorides give pure alkyl halides.
Assertion (A): The boiling points of alkyl halides decrease in the order: RI > RBr > RCl > RF
Reason (R): The boiling points of alkyl chlorides, bromides and iodides are considerably higher than that of the hydrocarbon of comparable molecular mass.
Assertion (A): Presence of a nitro group at ortho or para position increases Reason (R): Nitro gjoup, being an electron withdrawing group decreases the electron density over the benzene ring.
Assertion (A): It is difficult to replace chlorine by -OH in chlorobenzene in comparison to that in chloroethane.
Reason (R): Chlorine-carbon (C – Cl) bond in chlorobenzene has a partial double bond character due to resonance.
Arrange each set of compounds in order of increasing boiling points.
(i)Bromomethane, Bromoform, Chloromethane, Dibromomethane.
(ii)1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.
