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Q9.4(iii):
Write IUPAC names of the products obtained by the ozonolysis of the following compounds : (iii) 2-Ethylbut-1-ene
Solution :
Step 1: Structural Representation of 2-Ethylbut-1-ene
The chemical structure of 2-ethylbut-1-ene is defined by a four-carbon principal chain with a double bond at the $C_1$ position and an ethyl substituent at the $C_2$ position. The condensed structural formula is $CH_2=C(C_2H_5)CH_2CH_3$.
Step 2: Mechanism of Ozonolysis
Ozonolysis involves the addition of ozone ($O_3$) to the carbon-carbon double bond to form an intermediate ozonide, followed by reductive cleavage using zinc dust ($Zn$) and water ($H_2O$). [Per the cleavage mechanism of alkenes during oxidative ozonolysis]:
- The double bond ($C=C$) is cleaved entirely.
- Each carbon atom involved in the double bond is converted into a carbonyl group ($C=O$).
Step 3: Identification of Cleavage Products
Given the structure $CH_2=C(C_2H_5)CH_2CH_3$:
- Part A (The $C_1$ fragment): The terminal $CH_2$ group is oxidized to formaldehyde ($HCHO$).
- Part B (The $C_2$ fragment): The $C_2$ atom, which is bonded to an ethyl group and the rest of the original chain (an ethyl group as well), becomes a ketone. Specifically, it is a $3$-pentanone derivative, but based on the specific connectivity: the $C_2$ is bonded to an ethyl group ($-CH_2CH_3$) and another ethyl group coming from the parent chain. Wait—re-evaluating the parent structure 2-ethylbut-1-ene:
Structure: $CH_2=C(CH_2CH_3)CH_2CH_3$.
The $C_2$ position is bonded to two identical ethyl groups.
Step 4: Final IUPAC Nomenclature
Following the cleavage of the $C=C$ bond:
| Fragment | Resulting Structure | IUPAC Name |
|---|---|---|
| $C_1$ | $HCHO$ | Methanal |
| $C_2$ | $O=C(CH_2CH_3)_2$ | Pentan-3-one |
The reaction equation is represented as:
$CH_2=C(C_2H_5)CH_2CH_3 + O_3 \xrightarrow[H_2O]{Zn} HCHO + CH_3CH_2COCH_2CH_3$Final Solution: The products obtained are Methanal (formaldehyde) and Pentan-3-one (diethyl ketone).
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(ii): How would you convert the following compounds into benzene? (ii) Ethene
- 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(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
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