R.

J INTERNATIONAL PUBLIC SCHOOL

STD 12 Science Chemistry
Date : 04-05-2023 halo alkanes and haloarenes
Time : 0 Minute 12 sci Total Marks : 20

[10]
* Section -A Answer the following question (Each question 1 marks)
1. Arrange the compounds of each set in order of reactivity towards SN2 displacement:
1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-
methylbutane.

Ans. :
1-Chlorobutane to n-octane.
dry ether

2CH 3 CH 2 CH 2 CH 2 − Cl + 2Na −−−−−→ CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

−2NaCl

1 − Chlorobutane n-octane

2. Write the equations for the preparation of 1-iodobutane from:

but-1-ene.

Ans. :
1,4-Dibromobut-2-ene.
Br − CH 2 − CH = CH − CH 2 − Br

1 2 3 4

3. How the following conversion can be carried out?

2-Chloropropane to 1-propanol.

Ans. :
In the 2, 2, 3-Trimethyl-3 bromopentane compounds, there are two different
β − hydrogen atoms. Thus, dehydrohalgenation of the compounds yields two alkenes.

Saytzeff’s rule implies that in dehydrohalgenation reaction, the alkene having a greater
number of alkyl groups attached to a doubly bonded carbon atoms is perferably produced.
Hence, alkene (I) is the major product in this reaction.
4. How the following conversion can be carried out?
Benzene to diphenyl.

Ans. :
KCN, aq.ethanol

CH 3 − CH 2 − CH = CH 2 −−−−−−−−−−−−−−−−→ CH 3 − CH 2 − CH 2 − CH 2 + Br
(Anti-Markovnikov addition)

But-1-ene 1 − Bromobutane

⏐
⏐
Finkelstein reaction⏐Nal, dry acetone
⏐
↓
[1] CH 3 − CH 2 − CH 2 − CH 2 − I

n-Butyliodide

5. Write the structure of the major organic product in each of the following reaction:
CH 3 CH 2 CH 2 OH + SOCl 2 →
Ans. :

1-chlorobutane.

acetone

CH 3 − CH 2 − CH 2 − CH 2 Cl − Nal −−−−→ CH 3 CH 2 CH 2 − CH 2 − I

+ NaCl

1-chloro butane Sodium iodode

6. Write structures of the following compounds:

1-Chloro-4-ethylcyclohexane.

Ans. :

7. What happens when:

methyl bromide is treated with sodium in the presence of dry ether,

Ans. :

8. Write the structure of the major organic product in each of the following reaction:
peroxide

CH 3 CH 2 CH = CH 2 + HBr −−−−−→

Ans. :
But-1-ene to but-2-ene.
Br

HBr

CH 3 CH 2 CH − CH 2 −−−−−−−−−−−−−→ CH 3 CH 2 CHCH 3
(Markovnikov addition)

But-1-ene 2-Bromobutane

⏐
⏐
− HBr⏐KOH(alc)Δ
⏐
↓
[2]
CH 3 CH = CHCH 3

2 − Bromobutane

9. What happens when:

methyl chloride is treated with KCN?

Ans. :
CH 3 C(Cl) (C2 H 5 )CH 2 CH 3
Cl

3 4 5
CH 3 ¯¯¯ C¯¯¯ CH 2 ¯¯¯ CH 3

2
CH 2

1
CH 3

3-chloro 3-methyl pentane

(tertiary alkyl halide).
10. Write the structure of the major organic product in each of the following reaction:
acetone

CH 3 CH 2 CH 2 Cl + NaI −−−−→
heat

Ans. :

[10]
*
Section - A
Answer the following question (Each question 2 marks)
11. In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?
i.

ii.

Ans. :
i. Greater the stability of the carbocation, faster is the rate of SN1 reaction. Since
tertiary carbocation 2-chloro-2-methylpropane is more stable than secondary
[3]
carbocation 3chloropentane. Hence SN1 reaction proceeds via tertiary cation such as 2-
chloro-2 methylpropane.

ii. Greater the stability of the carbocation, faster is the rate of SN1 reaction. Since
secondary carbocation 2-chloroheptane is more stable than primary carbocation 1-
chlorohexane. Hence SN2 reaction proceed via secondary cation such as 2-
chloroheptane.

12. Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2
mechanism? Explain your answer.
CH 3 CH 2 CH 2 CH 2 Br or CH 3 CH 2 CHCH 3

Br

Ans. :
CH 3 CH 2 CH 2 CH 2 Br - 1º alkyl halide
CH 3 CH 2 CH(Br)CH 3 - 2º alkyl halide
As steric hindrance in 2º alkyl halide is more, thus reactivity of CH 3 CH 2 CH 2 CH 2 Br
> CH 3 CH 2 CH(Br)CH 3 .
13. How the following conversion can be carried out?
Aniline to chlorobenzene.

Ans. :

14. How the following conversion can be carried out?

Chlorobenzene to p-nitrophenol.

Ans. :

15. Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2
mechanism? Explain your answer.
CH 3

CH 3 CH 2 CHCH 3 or H3 C − C − Br [4]
∣ ∣

Br CH 3

Ans. :
CH 3 CH 2 CH(Br)CH 3 - 2º alkyl halide
(CH 3 )3 CBr - 3º alkyl halide
As steric hindrance in (CH 3 )3 CBr is more, thus it is less reactivity then CH 3 CH 2 CH(Br)CH 3 .

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