CHEMISTRY ASSIGNMENT
(ALKYL HALIDE,ARYLHALIDE,ALCOHOL,PHENOL,ETHER)
PART-1
Reasoning question:1. o-nitro phenol is more acidic then o-methoxy phenol.The C-O bond is much shorter in phenol
then in ethanol.
2. o-nitro phenol has lower B.P then p-nitro phenol.
3. explain the fact that in aryl alkyl ether (i)The alkoxy group activates the benzene ring towards
electrophilic substitution(b)And direct the incoming substituent to ortho and para position in
benzene ring.
4. Tert-butyl chloride on heating with sodium methoxide gives 2-methylpropane instead of
tertbutyl methyl ether.
5. o-nitro phenol is more steam volatile then p-nitro phenol.
6. Phenol does not give protonation reaction readily.
7. Why phenol is stronger acd then alcohol.
8. Why phenol undergoes electrophilic substituion reaction more easily then benzene.
9. The B.P of alcohol decreases with increasing in branching of the alkyl chain.
10. Propanol has higher boiling point then butane.
11. Phenyl methyl ether react with HI to give Phenol and methyl iodide not Iodo benzene and
Methyl alcohol Why?
12. Preparation of Ethers by acid dehydration of secondary and tertiary alcohl is not suitable
method.
13. Explain the Mechanism of acid catalysed dehydration of ethyl alcohol on heating with
Conc.H2SO4.
14. The Dipole moment of chlorobenzene is lower then that of cyclohexyl chloride?
15.Which of the following has the highest Dipole moment.(CH2Cl2, CHCl3, CCl4)
16.p-dichloro benzene has higher M.P and lower solubility then those of m and o-isomers.
17. Which isomer of C5H11Cl has the highest B.P why?
18. why chloroform is soluble in water although it is polar.
19.Which isomer of C4H9Cl has the lowest and highest B.P.
20.Explain Why Haloarenes are insoluble in water but are soluble in benzene?
21..Alkyl halides,through polar,are imiscible with H2O why
22.n-butyl bromide has higher B.P then t-butyl bromide?
23. Neo-Pentyl chloride does not follow SN2 mechanism
24.)Why is it that haloalkanes are more reactive then haloarenes towards nucleophile?
25.Explain Racemic mixture is optically inactive?
26.The presence of nitro group at o/p-position increases the reactivity of haloarenes towards
nucleophilic substitution reaction.
27. How CH3Br be preferentially converted to methyl isocyanide?
28.The C-Cl bond length in chlorobenzene is shorter then that in CH3-Cl.
29. Grignard’s reagent should be prepared under anhydrous condition?
30.The Order of reactivity of Haloalkanes R-I > R-Br > R-Cl why?
31. Out of SN1 and SN2 ,which reaction occurs with
(a)Inversion of configuration (b)Racemisation
32.Racemisation occures in SN1 reaction Why?
33.Chlorobenzene is treated with CH3COCl in the presence of Anhyd.AlCl3.
34. How CH3Br be preferentially converted to methyl isocyanide?
35.The C-Cl bond length in chlorobenzene is shorter then that in CH3-Cl.
36.Chloroform is stored in closed dark brown bottles.
PART-2
2.Which would undergoes SN2reaction faster in the following pair?
(i) CH3Br & CH3I
(ii) 1-bromo-2-methyl butane &2-bromo-2-methyl butane
(iii)2- bromo-2-methyl butane,1-bromo pentane ,
2-bromo pentane
(iv)1-bromo-3-methyl butane,2-bromo-2-methyl butane
3-bromo-2-methyl butane
(v)1-bromo butane,1-bromo-2,2-dimethyl propane,
1- bromo-2-methyl butane,1-bromo-3-methyl butane.(i) (vi)Ethy bromide & t-butyl bromide
(vii) Ethyl bromide & Ethyl Iodide
(viii) 1-bromo pentane & 2-bromo pentane
(ix) 1-bromo butane & 2-bromo butane
(x) Methyl bromide & Methyl Iodide
(xi) (CH3)3CCl & CH3Cl
(xii) C6H10CH2Cl & Cyclohexyl chloride
(xiii) 1-iodopentane & 1-chloro pentane
1.Which would undergoes SN 1reaction faster in the following pair?
(i) 3-chloro pentane & 1-chloro butane
(ii) 2-chloro-2-methyl propane & 3-chloro pentane
(iii) (CH3)3CCl & CH3Cl
(iv) CH3CH2CH2Br & CH3CH(Br)CH3
(v)3-chloro hexane & 1-chloro pentane
PART-3
Answer the following Questions?
(i)Draw the isomers of C7H7Cl and which isomer have weakest c-cl bond .
(ii)Most reactive compound for chlorination in pres. of light (i)Toluene (ii)Ethyl benzene
(iii)Isopropyl benzene
(iii)1-phenyl prop-1-ene react with HBr gives_____.
(iv)Why Iodination of Benzene is difficult.
(v)How is chloro benzene prepared from Sand mayer’s reaction & Gatter mann reaction.
(v)Explain Balz Schiemann reaction
(vi)Cyclohexanol react with SoCl2 gives _____.
(vii)Silver benzoate on Hunsdiecker reaction gives ____.
(viii)Bromocyclo hexane react with Mg & then hydrolysis
(ix)Convert BDC to biphenyl.
(x)Give a chemical test to distinguish between Benzyl chloride and Chloro benzene .
(xi)Chloro benzene react with (i)CH3Cl/anhydAlCl3
(ii)CH3COCl/anhyd.AlCl3
(xii)p-nitro chloro benzene undergoes Dows process gives
PART-4
1.CONVERSION
(i) Ethane to Bromo ethane
(ii)Benzene to biphenyl
(iii)1-chloro butane to n-octane
(iv)Propene to propyne
(v)Toluene to benzyl alcohol
(vi)Ethanol to ethyl fluoride
(vii)Propene to 1-nito propane
(viii)Chloro ethane to Butane
(ix)Benzene to 4-bromo nito benzene
(x)Propene to propan-1-ol
2. A hydrocarbon C5H10 does not react with Cl2 in dark but gives a single monochloro
compound C5H9Cl in bright sunlight identify the hydrocarbon.
3. out of C6H5CH2Cl and C6H5CHClC6H5 which will hydrolysed easily by aqueous KOH.
4. The treatment of alkyl chloride with aqueous KOH leads to the formation of alcohol but in the
presence of alc.KOH alkene is the major product why?
5. Primary alkyl halide C4H9Br (a)reacted with alcoholic KOH to give comp. B.Comp.B is
reacted with HBr to give C which is an isomer of A.When A react with Na metal it gives comp.
D. Identify A,B,C,D.
PART-5
(i)2-bromo pentane is treated with alco. KOH.
(ii)Ethyl Bromide react with Aqu.KOH.
(iii)Methyl beomide react with Alc.KCN.
(iv)Chloro benzene is treated with Cl2/FeCl3.
(v)1-chloro propane is treated with AgNO2.
(vi)Ethyl bromide react with Na metal in pres of dry ether.
(vii)Ethyl chloride react with AgCN gives.
(viii)Ethyl bromide react with Mg & then undergoes hydrolysis gives.
(ix)Chloro benzene react with Na metal gives_.
(x)n-Butyl bromide treated with Alc.KOH.
(xi)Chloro benzene is subjected to hydrolysis.
(xii)Propyl chloride react with NaI in presence of acetone
(xiii)Sodium phenoxide react with C2H5Cl__.
(xiv)But-1-ene react with HBr in presence of Peroxide.
(xv)2-methyl but-2-ene react with HBr gives__.
PART-6
What happenes when:(i)Phenol react with Bromine Water
(ii)Phenol react with Br2 in presence of CCl4/CS2
(iii)Phenol react with Conc.HNO3/Conc.H2SO4
(iv)Phenol undergoes Oxidation
(v)Butanol react with excess oxidising agent
(vi)Butan-2-ol react with excess oxidising agent
(vii)2-methyl propanol react excess oxidising agent
(viii)Ethyl alcohol heated with Cu/3000C.
(ix)Propene react with B2H6/3H2O/OH(x)Cyclohexanone react with CH3MgBr
(xii)Cyclo-hex-2-en-1-one oxidation by PCC
(xiii)Salicyclic acid reactwith (CH3CO)2/CH3COOH
(xiv)Hydroboration of butene followed by oxidation in H2O2 in alkaline medium.
(xv)Dehydration of (CH3)3C-OH by heat in with 20% H3PO4 at 358K.
PART-7
Name Reaction:(i)Reimer Tiemann reaction
(ii)Kolbe’s Synthesis
(iii)Friedel craft alkylation and acylation of phenol
(iv)Dows process
(v)Williamson’s Ether Synthesis
(VI)Wurtz reaction
(vii)Fittig reaction
(viii)Wurtz fittig reaction
(ix)Sandmayers reaction
(x)Coupling reaction
(xi)Balz schiemann reaction