Chemistry Assignment Name:…………………………………

Course : POC Batch:………………………………….

Date : 28-10-2022 Date of Completion:………………….

ALKYL HALIDE / ARYL HALIDE

1- Methods of preparation → (Miscellaneous Methods)

/∆ /∆
(i) ∆ ? (ii) ??

CH=CH2 CH2 OH

(iii) ? (iv) ?

CH2 CH=CH2 CH2-CH3

/
(v) (vi) ?
CH3
CH CH=CH2
CH3 / /
(vii) ? (viii) ?

(ix) CH2 COOAg ? (x) O+PCl5 →
→?

CH2 OH

(xi) CH2 OH+SOCl2→? (xii) CH2 OH ?

(xiii) CHO ? (xiv) + Br2 ?

(xv) + Br2 ? (xvi) + Br2 ?

(xvii) CH3 –CH CH+HOCl ? (xviii) C6H5 CH= CH CH3 ?

2 – Select the True/False statements from the following-

following

i. Alkyl halides are in soluble in water while soluble in non polar solvents.
ii. The order of boiling point is RI>RBr > RCl > RF.
iii. The order of dipole moment R-Cl>R-F>R-Br>R-I.
R
iv. The density of water and alkyl halides follow the order R-I>R-Br>H
R 2O>R-Cl>R-F.
O>R
v. The order of bond strengthth isR-F>R-Cl>R-Br>R-I.
isR
vi. The order of reactivity towards SN1 is 3º > 2º > 1º.
vii. The order of reactivity towards SN2 is 1º > 2º > 3º.
viii. Secondary alkyl halide can give elimination or substitution when treated with NaNH2.
ix. The order for SN1 among alkyl halide is R-I>R-Br>R-Cl>R-F.
R
x. The order for SN2 among alkyl halide is R-I>R-Br>R-Cl>R-F.
R
xi. SNi and NGP Reactivityss retain the configuration of stereoisomers.
xii. E1cb gives anti Saytzeff procluet as major product.
xiii. The order of reactivity towards E1cb is R-F>R-Cl>R-Br>R-I.
xiv. The order of reactivity for E1 and E2 both is 3º > 2º >1º.
xv. OH- iss better nucleophile than SH- in protic polar solvent.

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 xvi. The order of nucleophilicity in polar protic solvent is I ∙ ∙ > Br ∙ ∙ > Cl∙ ∙ >F ∙ ∙.
xvii. In SN2 inversion of configuration takes place in most of the cases.
xviii. A stronger nucleophile like SH ' give SN2 with 3º halide.
xix. A stable carbanion is formed in E1cb, which gives major product.
xx. Allyl chloride is more reactive than n-propyl chloride towards SN2 Reactivity.

3 – Arrange the following in decreasing order as instructed-

(i) (CH3)3C−Br, CH3−CH2−Br, (CH3)2CHBr, CH3Br (SN1 Reactivity)

(ii) (CH3)3C−Br, (CH3)3C−I, (CH3)3C−Cl, (CH3)3C−F (SN1 Reactivity)
(iii) CH2=CH−CH2−Cl, CH2=CH−CH2−I, CH2=CH−CH2−F, CH2=CH−CH2−Br (SN1
Reactivity)
(iv) (CH3)3C−Cl, CH2=CH−CH2−Cl, CH3−CH2−Cl, (CH3)2CH−Cl (SN1 Reactivity)

CH3

(v) C6H5−CH2−Br, C6H5−Br, C6H5−CH2−CH2−Br, C6H5−CH−Br (SN1 Reactivity)

CH3 CH3 CH3 CH3

(vi) CH−I, CH−Br, C−F, C−Cl (SN2 Reactivity)
CH3 CH3 CH3 CH3
CH3
(vii) CH3−CH−CH2−Cl, CH3 C−Cl, CH3–CH2−CH2−CH2−Cl (SN2 Reactivity)
CH3
(viii) C6H5−Cl, C6H5−CH2−Cl, CH3−CH2−Cl, CH3−CH2−Cl (SN2 Reactivity

(ix) C2H5−Cl, C2H5−F, C2H5−Br, C2H5−I (SN2 Reactivity)

CH3
(x) CH2=CH−CH2−Br, CH−Br, CH2=CH−CH2−I, C2H5−Br (SN2 Reactivity)
CH3
CH3 CH3 CH3 CH3
(xi) CH−Br, CH−F, CH−Cl, CH−I (E1cb)
CH3 CH3 CH3 CH3

O
(xii) CH2=CH−CH2−F, CH3−C−CH2−CH2−F, CH3−CH2−CH2−CH2−F (E1cb)

CH3 CH3 CH3 CH3

(xiii) CH3 C−Br, CH3 C−I, CH3 C−Cl, CH3 C−F (E1 Reactivity)
CH3 CH3 CH3 CH3
CH3 CH3
(xiv) CH−Br, CH3 C−Br, CH2=CH−CH2−Cl, CH3−CH2−Br (E1 Reactivity)
CH3 CH3
O O
CH3 CH3
(xv) CH3 C −O−S− , CH3 C−O−S− −CF3 (E1 Reactivity)
CH3 CH3
O O
CH3 CH3
(xvi) CH3 C−Br + OH ' , CH3 C−Br + H2O (E1 Reactivity)
CH3 CH3

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 CH3 Me
(xvii) CH3 C Cl + OH ' , Me C Cl + NH*∙∙ (E2 Reactivity)
CH3 Me
CH3
(xviii) CH3−CH2−Br, CH−CH2−Br, CH3−C−Br, CH2 = CH−Br (E2 Reactivity)

CH3 CH3

CH3 CH3 CH3 CH3

(xix) CH3 C−Cl, CH3 C−Br, CH3 C−F, CH3 C−I (E2 Reactivity)
CH3 CH3 CH3 CH3
(xx) C6−H5, C6H5−Cl, C6H5−I, C6H5− Br O
(SNAr)
O
Br Br Br C Br
(xxi) H2N , HO , HO , Ph−O (NGP)

Cl Cl Cl Cl
Br Br
(xxii) , , (Benzyne mechanism)

CH3 CH3

4 – Write the product(s) in the following chemical reactions.

+,-. / 0
(i) CH3−Br + Mg ? (ii) C6H5−Cl + Mg ?
12.4 1 5.4
(iii) C2H5−Br ? (iv) C2H5−Br ?
12. 16- 12. 1
(v) C6H5−Cl ? (vi) CH2=CH−Br ?
12.4 12.78
(vii) CH2=CH−CH2−Cl ? (viii) C6H5−CH2−Cl ?
∙∙ ∙∙
(ix) C2H5−Br ? (x) C2H4Br2 ?
12.4 1
(xi) CH3−CH−Br (xii) C6H5−CH2−Br ?
CH3

CH3 9
Br
12.4
(xiii) CH3 C−Cl ? (xiv)
CH3
(78 ; ) 1 5.4
(xv) CH2=CH−CH2−Cl ? (xvi) CH3−CH2−Br ?

Me
1 H Br 1 5.4
(xvii) C6H5−Cl ? (xviii) H Br ?
Me Me
H Br 1 Br
12.4
(xix) Br H ? (xx) ?
(leq.)(SN1)
Me I

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 F

1 /∆
12. 1 (xxii) ?
(xxi) ? (leq.)

Br Cl
Cl Br
NO2
1
12.4 (xxiv) ?
(xxiii) ?
Br
F
Cl
CH2-CH2-Br
12. 1
12.4 (xxvi) ?
(xxv) ?
Cl Cl Br

5. Combined concept problems.

1 5.4 / ? 1
(i) C2H5OH = > @ A
12.4 B /∆ / ?
(ii) CH3−CH2OH = > @ A

Br
(CD E;F E) FB /∆ GHI JKL.MEF
(iii) = > @ A
CH3
NK /OP JQ.MEF RNK HF∙ ∙
(iv) (leq.)
= > @ A

CH3
CH
CH3 NK /OP JKL.MEF FS EB /∆ FB /∆
(v) = > @ A

NK /OP CKL.MEF JKT.MUVE? FB /∆

(vi) = > @ A

NK /NNK? JWN.MEF NF XNF (Y)ES

(vii) = > @ (ii)(Zn/H2O) A

CH2−Br
JQ.MEF HENK GJZ ([UZ)
(viii) (leq.)
= > @

Br
CH3 EN F FI] GF ∙∙ FI]
(ix) CH3 C − Br A H2O2
B C D
CH3
F E FNK JKL.MEF (Y)IFS
(x) CH3−CH−CH2−Br A B C (ii)H2O2/OH-
D

CH3

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 ANSWER
Br Br Cl Cl Cl

1- (i) CH2 CH2 CH2 (ii) CH2 CH2 CH2 CH2 (iii) Ph CH CH3

(iv) Ph CH2 I (v) Ph CH CH=CH2 (vi) Ph CH CH3

Br Cl
CH3
(vii) Ph C Cl (viii) Ph CH2 CH2 Br (ix) CH2 Br
CH3
CH2 Cl
Cl
(x) (xi) CH2 Cl (xii) CH2 I
Cl Br CH2 Br
Cl
(xiii) CH (xiv) (xv)
Cl
Br Br
Br
OH OH Cl

(xvi) (xvii) CH3 CH CH2Cl (xviii) C6H5 CH CH CH3

Br

2- (i) (T) (ii) (T) (iii) (T) (iv) (T) (v) (T) (vi) (T) (vii) (T)
(viii) (F) (ix) (T) (x) (T) (xi) (T) (xii) (T) (xiii) (T) (xiv) (T)
(xv) (F) (xvi) (T) (xvii) (T) (xviii) (F) (xix) (T) (xx) (T)

3- (i) Ans. (i > iii > ii > iv) (ii) Ans. (ii > i > iii > iv) (iii) Ans. (ii > iv > i > iii)
(iv) Ans. (i > ii > iv > iii) (v) Ans. (iv > i > iii > ii) (vi) Ans. (i > ii > iv > iii)
(vii) Ans. ( i >iii > ii) (viii) Ans. (ii > iv > iii > i) (ix) Ans. (iv > i > iii > ii)
(x) Ans. (iii > i > iv > ii) (xi) Ans. (ii > iii > i > iv) (xii) Ans. (ii > iii > i)
(xiii) Ans. (ii > i > iii > iv) (xiv) Ans. (ii > i > iv > iii) (xv) Ans. (ii > i)
(xvi) Ans. (ii > i) (xvii) Ans. (ii > i) (xviii) Ans. (iii > ii > i > iv)
(xix) Ans. (iv > ii > i > ii) (xx) Ans. (i > ii > iv > iii) (xxi) Ans. (i > ii > iii > iv)
(xxii) Ans. (iv > ii > i > iii)

4- (i) CH3MgBr (ii) C6H5MgCl (iii) C2H5OH (iv) C2H4 (v) No reaction

(vi) No reaction (vii) CH2=CH CH2 OH (viii) C6H5 CH2 OH (ix) CH2=CH2
CH3
(x) CH≡CH (xi) CH3 CH=CH2 (xii) C6H5 CH2 OC2H5 (xiii) C=CH2
CH3
(xiv) (xv) CH2=CH CH2 OH (xvi) CH3 CH2 OC2H5

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 Br
(xvii) No reaction (xviii) Trans alkene (xix) Cis Alkene (xx)
O- O-
Type equation here NO2
Type equation here
(xxi) No reaction (xxii) (xxiii) (xxiv)

Cl F
CH=CH2
(xxv) (xxvi)

5- (i) A = C2H5Cl, B = C2H4, C = CH2BrCH2Br, D = CH≡CH

(ii) A = CH3CH2I, B = CH3CH2OH, C = CH2=CH2, D = CH2BrCH2Br

OH
(iii) A = B= C= D=
Br
(iv) A = Ph CH2 Cl, B = PhCH2 OH, C = Ph CH2 Cl, D = Ph CH2SH

Me Me

(v) A = Ph C Cl, B = PH CH=CH2, C = Ph C OH, D = Ph C=CH2

Me Me Me Me
OH
Cl OH
(vi) A = , B= , C= , D=

Cl CHO
(vii) A = , B= , C= , D=
Cl CHO

CH2−OH CH2−Cl CH2−F

(viii) A = , B= , C=
Br Br Br

CH3 CH3 CH3 CH3

(ix) A = C=CH2, B = CH CH2 Br, C= C=CH2, D = CH3 C Br
CH3 CH3 CH3 CH3

CH3 CH3 CH3 CH3

(x) A = CH3 C OH, B = CH3 C Cl, C= C=CH2, D= CH CH2 OH
CH3 CH3 CH3 CH3

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