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Q9.20(ii):
How would you convert the following compounds into benzene? (ii) Ethene
Solution :
Given Variables & Initial Setup
The objective is to convert ethene ($CH_2=CH_2$) into benzene ($C_6H_6$). This transformation involves a transition from a simple two-carbon alkene to a stable six-carbon aromatic hydrocarbon. The process requires a controlled polymerization mechanism followed by aromatization.
Step 1: Catalytic Hydration to Ethanol
Ethene is reacted with steam in the presence of a phosphoric acid ($H_3PO_4$) catalyst at high temperature and pressure to produce ethanol.
$CH_2=CH_2 + H_2O \xrightarrow{H_3PO_4 / \Delta} CH_3CH_2OH$
[Per the mechanism of electrophilic addition/hydration of alkenes].
Step 2: Oxidation to Ethanal
Ethanol is oxidized to ethanal using copper (Cu) at 573 K, which acts as a dehydrogenation catalyst.
$CH_3CH_2OH \xrightarrow{Cu, 573K} CH_3CHO + H_2$
[Per the principle of catalytic dehydrogenation of primary alcohols].
Step 3: Aldol Condensation and Dehydration
Ethanal undergoes base-catalyzed aldol condensation followed by dehydration to form crotonaldehyde, which is then further processed or effectively polymerized. However, a more direct route for the industrial conversion involves the cyclic polymerization of acetylene.
Step 4: Alternative Direct Route - Bromination and Dehydrohalogenation
1. Bromination: Ethene reacts with Bromine to form 1,2-dibromoethane.
$CH_2=CH_2 + Br_2 \rightarrow BrCH_2-CH_2Br$
2. Dehydrohalogenation: Treatment with alcoholic $KOH$ yields ethyne (acetylene).
$BrCH_2-CH_2Br + 2KOH(alc.) \rightarrow HC\equiv CH + 2KBr + 2H_2O$
Step 5: Cyclic Polymerization
Three molecules of ethyne are passed through a red-hot iron tube at 873 K. This induces cyclotrimerization to form benzene.
$3HC\equiv CH \xrightarrow{\text{Red hot Fe tube, 873K}} C_6H_6$
[By the principle of thermal cyclotrimerization].
Summary of Reaction Sequence
| Step | Reagent/Condition | Product |
|---|---|---|
| 1 | $Br_2$ | 1,2-dibromoethane |
| 2 | $Alc. KOH$ | Ethyne |
| 3 | Red hot Fe tube | Benzene |
Final Solution: Ethene is converted to benzene by first reacting with $Br_2$ to form 1,2-dibromoethane, followed by dehydrohalogenation with alcoholic $KOH$ to produce ethyne, and finally performing a cyclic trimerization of three ethyne molecules at 873 K over a red-hot iron tube to yield $C_6H_6$.
More Questions from Class 11 Chemistry Hydrocarbons EXERCISES
- Q9.1: How do you account for the formation of ethane during chlorination of methane ?
- Q9.10: Why is benzene extra ordinarily stable though it contains three double bonds?
- Q9.11: What are the necessary conditions for any system to be aromatic?
- Q9.12(i): Explain why the following systems are not aromatic? (i)
- Q9.12(ii): Explain why the following systems are not aromatic? (ii)
- Q9.12(iii): Explain why the following systems are not aromatic? (iii)
- Q9.13(i): How will you convert benzene into (i) $p$-nitrobromobenzene
- Q9.13(ii): How will you convert benzene into (ii) $m$-nitrochlorobenzene
- Q9.13(iii): How will you convert benzene into (iii) $p$-nitrotoluene
- Q9.13(iv): How will you convert benzene into (iv) acetophenone?
- Q9.14: In the alkane $H_3C-CH_2-C(CH_3)_2-CH_2-CH(CH_3)_2$, identify $1^{\circ},2^{\circ},3^{\circ}$ carbon atoms and give the number of H atoms bonded to each one of these.
- Q9.15: What effect does branching of an alkane chain has on its boiling point?
- Q9.16: Addition of HBr to propene yields 2-bromopropane, while in the presence of benzoyl peroxide, the same reaction yields 1-bromopropane. Explain and give mechanism.
- Q9.17: Write down the products of ozonolysis of 1,2-dimethylbenzene ($o$-xylene). How does the result support Kekulé structure for benzene?
- Q9.18: Arrange benzene, $n$-hexane and ethyne in decreasing order of acidic behaviour. Also give reason for this behaviour.
- Q9.19: Why does benzene undergo electrophilic substitution reactions easily and nucleophilic substitutions with difficulty?
- Q9.2(a): Write IUPAC names of the following compounds : (a) $CH_3CH=C(CH_3)_2$
- Q9.2(b): Write IUPAC names of the following compounds : (b) $CH_2=CH-C \equiv C-CH_3$
- Q9.2(c): Write IUPAC names of the following compounds : (c)
- Q9.2(d): Write IUPAC names of the following compounds : (d)
- Q9.2(e): Write IUPAC names of the following compounds : (e)
- Q9.2(f): Write IUPAC names of the following compounds : (f)
- Q9.2(g): Write IUPAC names of the following compounds : (g)
- Q9.20(i): How would you convert the following compounds into benzene? (i) Ethyne
- Q9.20(iii): How would you convert the following compounds into benzene? (iii) Hexane
- Q9.21: Write structures of all the alkenes which on hydrogenation give 2-methylbutane.
- Q9.22(a): Arrange the following set of compounds in order of their decreasing relative reactivity with an electrophile, $E^+$ (a) Chlorobenzene, 2,4-dinitrochlorobenzene, $p$-nitrochlorobenzene
- Q9.22(b): Arrange the following set of compounds in order of their decreasing relative reactivity with an electrophile, $E^+$ (b) Toluene, $p-H_3C-C_6H_4-NO_2$, $p-O_2N-C_6H_4-NO_2$.
- Q9.23: Out of benzene, $m$-dinitrobenzene and toluene which will undergo nitration most easily and why?
- Q9.24: Suggest the name of a Lewis acid other than anhydrous aluminium chloride which can be used during ethylation of benzene.
- Q9.25: Why is Wurtz reaction not preferred for the preparation of alkanes containing odd number of carbon atoms? Illustrate your answer by taking one example.
- Q9.3(a): For the following compounds, write structural formulas and IUPAC names for all possible isomers having the number of double or triple bond as indicated : (a) $C_4H_8$ (one double bond)
- Q9.3(b): For the following compounds, write structural formulas and IUPAC names for all possible isomers having the number of double or triple bond as indicated : (b) $C_5H_8$ (one triple bond)
- Q9.4(i): Write IUPAC names of the products obtained by the ozonolysis of the following compounds : (i) Pent-2-ene
- Q9.4(ii): Write IUPAC names of the products obtained by the ozonolysis of the following compounds : (ii) 3,4-Dimethylhept-3-ene
- Q9.4(iii): Write IUPAC names of the products obtained by the ozonolysis of the following compounds : (iii) 2-Ethylbut-1-ene
- Q9.4(iv): Write IUPAC names of the products obtained by the ozonolysis of the following compounds : (iv) 1-Phenylbut-1-ene
- Q9.5: An alkene ‘$A$’ on ozonolysis gives a mixture of ethanal and pentan-3-one. Write structure and IUPAC name of ‘$A$’.
- Q9.6: An alkene ‘$A$’ contains three $C-C$, eight $C-H$ $\sigma$ bonds and one $C-C$ $\pi$ bond. ‘$A$’ on ozonolysis gives two moles of an aldehyde of molar mass 44 u. Write IUPAC name of ‘$A$’.
- Q9.7: Propanal and pentan-3-one are the ozonolysis products of an alkene? What is the structural formula of the alkene?
- Q9.8(i): Write chemical equations for combustion reaction of the following hydrocarbons: (i) Butane
- Q9.8(ii): Write chemical equations for combustion reaction of the following hydrocarbons: (ii) Pentene
- Q9.8(iii): Write chemical equations for combustion reaction of the following hydrocarbons: (iii) Hexyne
- Q9.8(iv): Write chemical equations for combustion reaction of the following hydrocarbons: (iv) Toluene
- Q9.9: Draw the cis and trans structures of hex-2-ene. Which isomer will have higher b.p. and why?
CBSE Solutions for Class 11 Chemistry Hydrocarbons
Chapters in CBSE - Class 11 Chemistry
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