Hand-Out Chemistry

Chapter 4 : Haloalkanes & Haloarenes
This particular chapter is divided in the following parts with the exam pont of view.
1.

Reasoning 2. IUPAC Naming 3.Mechanisms 4.Name Reactions 5.Conversions

RE ASONINGS
Q1.

In the following pairs of halogen compound which is faster under going SN2 Rx.
(a)
(d)

, &

(c)

Q2.

, &

(c)

C4H9 Br &

(CH3)3CCl & CH3Cl

Ans. (a)
(b)

, (b)

(1º Alkyl Halide) >

(2º Alkyl Halide)

(bigger size, better leaving group) >
C4H9Br (1º) >

(d)

(CH3)3 CCl < CH3Cl (1º Alkyl Halide)

Predict the order of reactivity of the following compounds in SN1 and SN2 Rx.
(a)

Ans. (a)

The four isomeric bromo-butanes

(b)

C6H5 CH2 Br, C6H5 CH (C6H5)Br, C6H5 CH (CH3)Br, C6H5C(CH3)(C6H5)

For SN1 Rx. (Reactivity depends on stability of carbo cation  3º > 2º > 1º)
CH3CH2CH2CH2Br < (CH3)2 CHCH2 Br < CH3CH2CH (Br)CH3 < (CH3)3 C. Br
For SN2 Rx ( less steric hindrance more reactive)
CH3CH2CH2CH2Br > (CH3)2CHCH2Br > CH3CH2CH (Br)CH3 > (CH3)3 C. Br

(b)

For SN1 Rx  C6H5 C(CH3)(C6H5)Br > C6H5CH(C6H5)Br > C6H5CH (CH3)Br > C6H5CH2Br
For SN2 Rx  C6H5CH2Br > C6H5CH (CH3)Br > C6H5CH(C6H5)Br > C6H5C(CH3)(C6H5)Br.

Q3.

Identify chiral and achiral molecules in each of the following pair :-

(a)

(b)

(c)

(d)

Ans. (a) & (c) With four different alkyl group.
Q4.

Although chlorine is an EWG yet it is ortho-para directing in electro plilic aromatic substitution Rx.

Ans. Chlorine shows –– I effect causing the intermediate carbocation will destabilize but +R effect of Cl stabilizes the intermediate
carbocation. The reactivity is controled by the stronger – I effect while orientation is centrolled by weaker reasone effect.
Q5.

Haloalkanes react with KCN to form RCN but with AgCN form RNC?

Ans. CN is an ambidient group (can be attached from both the ends). In KCN, it is ionic bond, the reaction occuss through C since C – C
bonds are more stronger while in AgCN (covelent bonding), only N electron pair is availale for bond formation.
Q6.

RCl is hydrolysed to ROH slowly but the reaction is rapid if a catalytic amount of KI is added to the reaction mixture.

Ans. I– is stronger nucleoplile so it replace Cl to form RI then RI is more hydrolysed to yield ROH due to I–ion is a better leaving group than
Cl–.
© 2012 Vidyamandir Classes Pvt. Ltd.
1
Chemistry/Class XII

CCl4 Cl CH2Cl2 > CHCl3 > CCl4  H C Cl H C > H Cl Cl Cl C > H Cl Cl Cl Q11. p-dichlorobenzene has high M. bromoform. (a) (b) Bromoform > dibromomethane > bromomethane > Chloromethane (BP moleculer wt. Out of C6H5CH2Cl and C6H5CHCl C6H5 which is Easily hydrolysed by KOH (aq. CH2Cl2. On reaction between SOCl2 and ROH. Why is sulphuric acid not used during the reaction of Alcohols with KI. Ans.) Ans. Chloromethane. chlorobenzene. more surface area less B. 4-Nitrochlorobenzene. Ans. 4-dinitrochlorobenzene Ans. Ltd. Write strictures and name. 6-trinitrochlorobenzene. The dipole moment of chloro benzene lower than cyclohexylchloride. 2. Q12. Haloalkanes give nucleophilic substitution while Haloarenes give Electrophilic substitution reactions. Chemistry/Class XII 2 © 2012 Vidyamandir Classes Pvt. (a)bromomethan . Why SOCl2 is used for preparation of Alkyl Halide from ROH. Q9. Among the aromatic compounds have moleculer formula C7H7Cl how many isomess are possible. we get RCl. RMgX is very reactive.P. Arrange the following in order of increasing ease towards nucleophile. Q8. C6H5CHClC6H5 is 2º alkyl halide which is more reactive under SN1 reaction but under SN2 reaction 1º alkyl halide (C6H5CH2Cl) is more hydrolysed. RMgX should be prepared under anhydrons conditions Ans. Q16. dichloromethane (b)1–chloropropane. Ans. Ans. p-dichlorobenzene has symmetrical structrre so its MP is high and solubitlity low. 2. Ans. so their C has more +ve character so they give nucleophilic substitution while haloarenes has a benzene ring which shows resonance. Sulphuric acid oxidises KI to I2. Arrange on the basis of increasing Boiling Point. It increase electron density at Cl atom makes it polar while in case chlorobenzene which has benzene ring as EWG and resonating ring it dipole meoment is lower.) Q10. haloarenes give electrophilic reaction due to –I effect and +R effect.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes Q7. they react with moisture present in apparatus or the starting material. HCl(g) and SO2(g) as escapible gases. 2. . 6 trinitrochlorobenzene > 2.P and low solubility than O-dichlorobenzene. Q13.Rx. 4.) Isopropyl chloride (side chain) < 1 chloropropane < 1 Chlorobutane (more branching. Haloalkanes are more polar than Haloarenes. isopropyl chloride. Q14. 4. Alkyl halide though polar not soluble in water. Cyclohexylchloride has cyclohexyl as a EDG group. 4-dinitrochlorobenzene > 4-nitrochlorobenzene > Chlorobenzene. Identity all the possible monochloro structural isomess that would be expected to form on free radical chloronation of (CH3)2CH CH2CH3. 1–chlorobutane. Ans. Alkyl halide cannot form H-bond with water molecules. Q15. Differentiate between (a) chiral and achiral. Ans. (b) retentin and inversion. Q17. Which of the following has highest dipole moment CH3Cl.

11 Reactio n rate determ ining factor Cataly sis By s teric hin drance By electr on ic facto r (stability o f R) Not catalysed by any cataly st (ph ase tran sfer) Cataly sed by L ewis and Brons ted acid s. 12 Chemistry/Class XII 3 © 2012 Vidyamandir Classes Pvt. Q19. Ltd. M E CH A N IS M S H H SN2 Mechanism: – OH + H Cl H HO Cl H H HO H (CH3)3 CBr S r. the attack from the back side pred ominates. e. Uses of freon 12. + H3C + –OH CH3 SN 2 Reaction s Step 2 (CH3)3COH S N 1 Reaction s   One: R : L  Nu  R : Nu  L T wo: 1. R  N u    2 Reactio n rate and order Secon d o rder: Rate  [Su bstrate] [Nu cleophile] or R ate = K 2[ RL] [:Nu] F irst order: Rate  [S u bstrate] or Rate =  1 [ RL] 3 M olecu larity Bim olecular Unim olecular 4 T S o f slow step – –   : Nu     C     : L : N u    C    : L    Nu : 5 Reactin g nucleophile The car bon of th e su bstrate is attacked by the nucleop hile. reaction between Alkyl halide and KOH(aq) yield Alcohol but with KOH(aq) yield alkenes. (I > Br > Cl > F) 8 Rear rangem ent No r ear ranged pr odu ct is fo rm ed ( except fo r allylic) Rear rang ed pr oducts can b e fo rm ed. What is enantionmers and racimic mixture. (ii) three isomeric monochlorides. Explain. Among the isomeric alkanes of moleculer formula C5H12 Identify the one than on photochemical chlorohation yields (i) A single monochloride. Aq.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes Q18. 6 Stereochemistry Co mplete inversio n of config ur ation takes places In version and reten tion takes place 7 Reactivity o rd er of alk yl halides M eth yl I > 1° > 2° > 3° halides. Q22. No . . Favou red by m ild an d lo w con centration of nucleoph iles 10 Po larity Favo ur ed b y s olvents of low p olarity Favou red by so lvents of high polarity.g. DDT. T he nucleo ph ile can attack the carbon o f the su bstrate fro m both sides. ( I > Br > Cl > F) 3° > 2° > 1° > methyl h alides. ACl 3. Facto rs 1 Nu mb er or Steps Step 1 CH3 + H3 C – H H CH3 SN1 Mechanism: + Cl CH3 – + Br . Q21. Vinyl choloride is hydrolysed more slowly than ethyl chloride Q20. exclu sively fro m th e back sid e.. R : L  Slow   R  :L   F ast  R : Nu 2. Which one is better nucleophile Br– and I–. Ho wever. Z nCl2 an d stro ng HA. Carbontetrachloride and Iodeform. 9 Nature o f nucleoph iles Favo ur ed b y s tro ng and high concentration of nucleop hiles. Allyl chloride is hydrolysed more radily than n-propyl chloride. (iii) Four isomeric monochloride.

AlCl3 2-Chloroacetophenone (Minor) O CH3 4-Chloroacetophenone (Major) 6. AlCl3 + 1-Chloro-2-methylbenzene (Minor) CH3 1-Chloro-4-methylbenzene (Major) Cl Cl O + H3C – C – Cl Cl O CH3 + Anhyd. Ltd. Friedel Crafts Reaction: Cl (solvent . Wurtz Reaction: RX  2Na  RX  R  R  2NaX 5. .Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes EtOH H 2O  nBuCN Write the mechanism of the following reaction: nBuBr  KCN  + + – – K CN + CH3 – CH2 – CH2 – CH2 – Br CH3 – CH2 – CH2 – CH2 – CN + KBr n-Butyl bromide n-Butyl cyanide NAME REACTIONS 1. Wurtz Fitting Reaction: X R + Na + RX Chemistry/Class XII Ether + NaX 4 © 2012 Vidyamandir Classes Pvt.Acetone) Cl Cl CH3 + CH3Cl Anhyd. Sandmeyer’s Reaction: + – N2X X Cu2X2 + Na 2. Finkelstein Reaction: RX  NaI  RI  NaX 3. Swarts Reaction: CH3 Br  AgF  CH3F  AgBr 4.

Ltd. the compound R–Br is CH3CHCH3 carbon atom to which MgBr is attached. D. dry ether Bromocydohexane H2O MgBr + Mg(OH) Br . Identify A. E. Therefore. C. R and R1in the following: dry ether Br + Mg (i) (ii) dry ether R – Br + Mg H2O A D 2O C B CH3CHCH3 D CH3 CH3 CH3 (iii) CH3 Na/ether R1 – X Mg D H2O E CH3 CH3 Br + Mg Ans. Fitting Reaction: X Ether + Na + RX + 2NaX CONVERSIONS Q1.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes 7. B. The halide. CH3 – C – X . . since D of D2O gets attached to the Cyclohexylmagnesium bromide (A) Cyclohexane (B) CH3CHCH3 . C is MgBr Br Isopropylmagnesium bromide 2-Bromopropane CH3 CH3 CHCH3 + Mg dry ether Br CH3CHCH3 D2O CH3CHCH3 . Therefore. R1 "X. compound MgBr (C) D CH3 tert-Butylhalide CH3 CH3 – C – MgBr D is CH3 tert-Butytmagnesiumbromide Chemistry/Class XII 5 © 2012 Vidyamandir Classes Pvt.

NH (vi) PCl5 AgF CH 3  CH 2  OH   CH 3  CH 2  Cl   CH 3  CH 2  F  POCl . (i) SOCl2 . NH3 HC  CH  NaNH 2   HC  CNa   CH 3CH 2  Cl HC  CNa   CH3CH 2C  CH  NaCl Chloroethane But 1 yne Br / UV light (ii) Br / CCl  HBr 2 2 4 CH 3  CH 3   CH 3  CH 2 Br  HBr    CH 2  CH 2    BrCH 2  CH 2 Br or heat KOH(alc. HCl (vii) CH 3  MgBr KCN(alc) Hydrolysis CH 3  Br   CH 3  CN   CH3 – C  NMgBr   CH3 – C = O   Propene 1-Bromopropane Propene 3 1.). How will you bring about the following conversions? (i) Ethanol to but-1-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-1-ene to but-2-ene (ix) 1-Chlorobutane to n-octane (x) Benzene to biphenyl.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes Q2. Ltd.). . (v) Br2 / CCl4 NaNH 2 CH 3  CH  CH 2  CH3  CHBr  CH 2 Br   CH3  C  CH Liq.  Ethane vic  Dibromide Bromoethane     CH 2  CHBr KOH(alc) Bromoethane (iii) Peroxide AgNO2 CH 3  CH  CH 2  HBr   CH3  CH 2  CH 2 Br   AgBr  CH3  CH 2  CH 2 NO 2 (iv) Do yourself. Pyridine CH 3CH 2OH   CH 3CH 2 Cl SO 2  HCl Ethanol Chloroethane   Liq.2-Dibromopropane 3 Ethanol Bromoethane 1-Nitropropane Chloroethane Propyne Ethyl fluoride H3O Acetonitrile CH 3 CH3 Propanone Br (viii) (ix) HBr  HBr CH 3CH 2 CH  CH 2   CH3CH2CHCH3   CH 3CH  CHCH 3 (Markovnikov addition ) KOH(alc. Ans.  But-1-ene 2-Bromobutane 2-Bromobutane dry ether 2CH3 CH 2 CH 2 CH 2  Cl 2Na   CH 3CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 2 NaCl 1-Chlordrutane n-Octane Br Na   Dry ether Br2 / Fe   dark (x) Benzene Chemistry/Class XII + 2NaBr Diphenyl Benzene 6 © 2012 Vidyamandir Classes Pvt.

Ltd. . ethanol CH3CH 2 Br  KCN   CH 3CH 2CN  KBr (Nucleophilic Bromobutane 5. acetone CH 3CH 2 CH 2 Cl NaI   CH 3CH 2 CH 2 I NaCl heat 1-Chloropropane (CH3 )3 CBr 2. 7. 4-dimethylhexane (x) 2-Methyl-1-propene to 2-chloro-2-methylpropane (xi) Ethyl chloride to propanoic acid (xii) But-1-ene to n-butyliodide (xiii) 2-Chloropropane to 1-propanol (xiv) Isopropyl alcohol to iodoform (xv) Chlorobenzene to p-nitrophenol (xvi) 2-Bromopropane to 1-bromopropane (xvii) Chloroethane to butane (xviii) Benzene to diphenyl (xix) tert-Butyl bromide to isobutyl bromide (xx) Aniline to phenylisocyanide Chemistry/Class XII 7 © 2012 Vidyamandir Classes Pvt. Butan-2-ol Cyanoethane substitution) (Williamson synthesis) C6 H5 ONa  C 2 H5 Cl   C6 H 5  O  C2 H 5  Sodium phenoxide Chloroethane Phenetole NaCl CH 3CH 2 CH 2 OH  SOCl2   CH3 CH 2 CH 2 Cl SO 2  HCl 1-Propanol 1-Chloropropane Peroxide CH3CH2 CH  CH 2  HBr   CH3CH 2 CH 2CH 2  Br (Anti-Markovnikov's But-1-ene 1-Bromobutane addition) Br 8.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes 1. 6. 1 Iodopropane  Finkelstein reaction   KOH 2-Bromo-2-methylpropane ethanol    heat CH3 – C = CH2 + KBr + H2 O (Dehydrohalogenation) CH3 2-Methylpropene 3. water CH 3CH(Br)CH 2CH 3  NaOH  CH 3CH(OH)CH 2 CH 3  NaBr 2-Bromobutane 4. CH 3CH  C(CH 3 ) 2  HBr    CH3 – CH2 – C – CH3 (Markovnikov 2-Methylbut-2-ene addition) CH3 2-Bromo-2-methylbutane Q3. How the following conversions can be carried out? (i) Propene to propan-1-ol (ii) Ethanol to but-1-yne (iii) 1-Bromopropane to 2-bromopropane (iv) Toluene to benzyl alcohol (v) Benzene to 4-bromonitrobenzene (vi) Benzyl alcohol to 2-phenylethanoic acid (vii) Ethanol to propanenitrile (viii) Aniline to chlorobenzene (ix) 2-Chlorobutane to 3. aq.

Ltd. liq. aq.2-Dibromobutane Br (iii) KOH(alc) /  HBr CH 3  CH 2  CH 2  Br   CH3  CH  CH 2   CH3 – CH – CH3 (Dehydrohalogenation) Markovnikov addition 1-Bromopropane CH2OH CH2Cl CH3 aq. 2H O (viii) Cu 2Cl2   2 Aniline Chemistry/Class XII Benzenediazonium chloride + N2 Chlorobenzene 8 © 2012 Vidyamandir Classes Pvt.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes (i) HBr/Peroxide (Nucleophilic substitution) CH3  CH  CH2   CH3  CH 2  CH2  Br   CH3  CH 2  CH2  OH (Anti-Markovnikov aq. aq. KOH/   (nucleophilic Cl2 / UV light   or heat (iv) substitution) Benzyl alcohol Benzyl chloride Toluene Br Br HNO /H SO Br /FeBr 3 2 4    (Nitration) 2 3   Dark (v) 2-Bromopropane Propene Bromobenzene Benzene NO2 4-Bromonitrobenzen 2 PCl5   –POCl .ethanol    KCl 3 1 CH2COOH 2-Phenylethanoic acid red P/Br2 KCN. NH3  CH3CH2CH  CH CH3CH2CH – CH2  196 K (Dehydrohalogenation) Br But-1-yne Br 1. 273278 K    NaCl. . –HCl (vi) CH2CN CH2Cl CH2OH H / H 2O Benzyl cyanide Benzyl alcohol (vii) (Hydrolysis)    KCN. ethanol CH 3  CH 2  OH   CH3  CH 2  Br   CH 3  CH 2  CN Ethanol Bromoethane + NH2 Propanenitrile – N2Cl Cl NaNO2  2HCl. KOH/ Propene 1-Bromopropane addition) Propan-1-ol O (ii) red P/Br2 Mg / ether CH 3CH 2 OH   CH3CH 2 Br   CH 3CH 2 MgBr Ethanol H2C – CH2 ether Ethyl magnesium bromide (Grignard reaction) Ethyl bromide red P/I H / H O 2 [CH3CH2 CH2 CH2 OMgBr]   Addition product KOH (alc) /  (Electrophilic addition) 2 CH 3CH 2 CH 2 CH 2 OH   CH 3CH 2 CH 2 CH 2  I   CH 3CH 2 CH  CH 2   (Dehydrohalogenation) Br / CCl 1-Butanol Iodobutane 4 But-1-ene 4 NaNH 2 .

. KOH/   CH 3  CH 2  CH 2  OH (Nucleophilic substitution) 1-Propanol OH (xiv) O O CrO 3 NaOI  CH3 – C – CH3   CH3 – C – ONa + CHI3 CH3 – C – CH3  (oxidation ) (Iodoform reaction) Isopropyl alcohol Iodoform Propanone Cl Cl Cl Cl NO2 HNO3 / H 2SO 4   (Nitration ) (xv) + + NO2 Chlorobenzene m-Chloronitrobenzene NO2 o-Chloronitrobenzene p-Chloronitrobenzene (Major product) Br (xvi) KOH(alc.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes CH3 CH3 Cl (ix) 2Na / dry ether  CH3 – CH2 – CH – CH – CH2 – CH3 + 2NaCl 2CH3 – CH – CH2 – CH3  (woody reaction ) 3. ethanol Hydrolysis CH 3  CH 2  Cl   CH 3  CH 2  CN  KCl    CH3  CH 2  COOH  (nucleophilic substitution) (xii) HBr / Peroxide Finkelstein reaction CH3  CH 2  CH  CH 2   CH3  CH2  CH 2  CH 2  Br   CH3  CH 2  CH 2  CH2  I (Anti-Markovnikov NaI.) /  (Anti-Markovnikov addition) CH3 – CH – CH3    CH3  CH  CH 2  HBr    CH3  CH 2  CH 2  Br Dehydrohalogenation HBr / Peroxides 2-Bromopropane (xvii) Propene 1-Bromopropane 2Na/dry ether CH 3  CH 2  Cl   CH 3  CH 2  CH 2  CH 3  2NaCl (Wurtz reaction) Butane Br Br2 / FeBr3   (xviii) Benzene Chemistry/Class XII 2Na / dry ether   (Fitting reaction ) + 2NaBr Biphenyl 9 © 2012 Vidyamandir Classes Pvt. Ltd.4-dimethylhexane 2-Chlorobutane CH3 CH3 (x) HCl   CH3 – C – CH3 CH3 – C = CH2  (Markovnikov 2-Methyl-1-propene addition) Cl 2-chloro-2-methylpropane (xi) KCN. dry acetone Ethylchloride But-1-ene H / H 2O Propanenitrile Propanoic acid 1-Bromobutane addition) n  Butyliodide Cl (xiii) KOH(alc) /  HBr / Peroxide  CH 3  CH  CH 2  HCl    CH3  CH 2  CH 2  Br CH3 – C – CH3  (Dehydrohalogenation) (Anti-Markovnikov addition ) 1-Bromopropane Propene 2-Chloropropane aq. aq.

Compound (b) is reacted with HBr to give (c) which is an isomer of (a). why ? (ii) What is known as a racemic mixture? Give an example. . + 3KCl + 3H2O Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b). Which one of these is more easily hydrolysed? Chemistry/Class XII 10 © 2012 Vidyamandir Classes Pvt.5-Dimethylhexane (d) Br HBr CH3 – C = CH2   CH3 – C – CH3 (Markovnikov addition) 2-Methylpropene (b) CH3 2-Bromo-2-methylpropane (c) (an isomer of (a)) PREVIOUS YEARS CBSE QUESTIONS 1. which one is more reactive in SN1 substitution reaction and why? 2010 A solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2Cl. (ii) Which of the following compound is more easily hydrolysed by KOH and why?CH3CHClCH2CH3 or CH3CH2CH2Cl (iii) Which one undergoes SN2 substitution reaction faster and why? 1. 2. 3KOH. 2. 2011 Write the IUPAC name of the following compound : (CH3)3CCH2Br Answer the following : (i) Haloalkanes easily dissolve in organic solvents. Ltd. Give the structural formula of (a) and write the equations for all the reactions. 2Na / dry ether 2CH3CH 2CH 2CH 2 Br   CH 3CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3  2NaBr (Wurtz reaction) n-Butyl bromide CH3 n-Octane CH3 CH3 2Na / dry ether CH3CHCH2Br   CH3CHCH2CH2CHCH3 + 2NaBr (Wurtz reaction) Isobutyl bromide (a) CH3 2. 1. C8H18which is different from the compound formed when n-butyl bromide is reacted with sodium. Answer the following questions: (i) What is meant by chirality of acompound? Give an Example. 2012 Explain the mechanism of acid catalysed hydration of an alkene to form corrouspounding alcohol. (iii) Of the two bromoderivatives. Ans.    (Carbylamine reaction) (xx) Phenylisocyanide Aniline Q4.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes CH3 Br (xix) CH3 KOH(alc) /  HBr / Peroxide  CH3 – C = CH2   CH3 – CH – CH2 – Br CH3 – C – CH3  (Dehydrohalogenation) (Anti-Markovnikov 2-Methylpropene addition) Isobutyl bromide Br Tert-Butylbromide NC NH2 CHCl3 . When (a) is reacted with sodium metal it gives compound (d). C6H5CH(CH3)Br and C6H5CH(C6H5)Br.

2. (ii) (a) How are the following obtained? (i) Benzoic acid and ethyl benzene. Which compound in each of the following pairs will react faster in SN2 reaction with –OH? Why? (2 marks) (i) CH3 Br or CH3 I (ii) (CH3)3 CCl or CH3Cl Answer: (i) CH3 I (ii) CH3Cl (a) State the IUPAC name of the following compound: (b) Complete the following chemical equations: H 2 O2 CH3 CH2 CH == CH2 + HBr Peroxide   Answer: (a) 1-Bromobut-2-ene (b) CH3 CH2 CH2—CH2Br 3. 1. How are the following conversions carried out? (i) Benzyl chloride to benzyl alcohol... Factors responsible for diminished reactivity of haloarenes towards nucleophilic reactions are: (a) Resonance effect (b) Difference in hybridisation of carbon atom in the C-X bond (c) Instability of phenyl cation (d) Electronic repulsions On the other hand. (ii) benzldehyde from toluene (b) Complete each systhesis by giving the missing material.. (ii) Methyl magnesium bromide to 2-methylpropan-2-ol State one use each of DDT and iodoform.. Typical reactions in this case are electrophilic substitution reactions... =========== Chemistry/Class XII 11 © 2012 Vidyamandir Classes Pvt.. (2 marks) Hint: Aryl halides contain a benzene ring.Hand-Out Chemistry Chapter 4 : Haloalkanes & Haloarenes 2. carbon carrying the halogen in haloalkanes is more electron deficient than in haloarenes. ... Pd-BaSO4 (ii) (iii) 1.. As a result haloalkanes undergo nucleophilic substitutions more readily than haloarenes. 2008 Explain as to why haloarenes are much less reactive than haloalkanes towards nucleophilic substitution reactions. 2009 Which ones in the following pairs of substances undergoes SN2 substitution reaction faster and why? (i) 2. reagent or products: (i) H2 C6 H5 COCl  . Ltd. 3.