An SN1 reaction occurs through the formation of a carbocation intermediate. Alkyl halide (I) is tertiary (3°), whereas (II) is secondary (2°). As a result, (I) forms a tertiary carbocation, while (II) forms a secondary carbocation. Since the rate of an SN1 reaction increases with carbocation stability, and a tertiary carbocation is more stable than a secondary carbocation, compound (I), i.e., 2-chloro-2-methylpropane, undergoes the SN1 reaction faster than compound (II), i.e., 3-chloropentane.
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प्रश्न
In the following pair of halogen compounds, which compound undergoes a faster SN1 reaction?
In the following pair of halogen compounds, which compound undergoes SN1 reaction faster and why?
लघु उत्तरीय
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उत्तर १
The activity of halogen compounds in SN1 reaction depends on the stability of the carbocation formed due to ionization. The order of stability is tertiary > secondary > primary. Hence, 3° alkyl chloride is more active than 2° alkyl chloride. Hence,3° alkyl chloride is more active in the SN1 reaction.
The compound which react faster is:
The carbocation, which will be more stable and responsible for the faster reaction, is:
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उत्तर २
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Notes
Students should refer to the answer according to their questions.
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अध्याय 6: Haloalkanes and Haloarenes - Intext Question [पृष्ठ १८६]
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संबंधित प्रश्न
Write the structure of an isomer of compound C4H9Br which is most reactive towards SN1 reaction
Write the main products when methyl chloride is treated with AgCN.
What are ambident nucleophiles? Explain with an example.
How will you bring about the following conversion?
Toluene to benzyl alcohol
What happens when ethyl chloride is treated with aqueous KOH?
Which would undergo SN2 reaction faster in the following pair and why ?
CH3 – CH2 – Br and CH3 – CH2 – I
What is the action of the following on ethyl bromide
alcoholic solution of potassium hydroxide.
What is the action of the following on ethyl bromide?
silver acetate
In a coordination entity of the type [PtCl2(en)2]2+ which isomer will show optical isomerism?
Which of the following is an example of SN2 reaction?
Which of the following reactions is an example of nucleophilic substitution reaction?
Racemic compound has ____________.
Which of the following is a chiral compound?
The increasing order of reactivity towards SN1 mechanism is:
(I) \[\begin{array}{cc}
\ce{CH3-CH-CH2-CH3}\\
|\phantom{........}\\
\ce{CH3}\phantom{.....}
\end{array}\]
(II) CH3CH2CH2Cl
(III) P–CH3O–C6H4–CH2Cl
Which of the following compounds will give a racemic mixture on nucleophilic substitution by OH ion?
1-Bromoethane, 1-Bromopropane, 1-Bromobutane, Bromobenzene
Read the passage given below and answer the following question:
Nucleophilic substitution reaction of haloalkane can be conducted according to both SN1 and SN2 mechanisms. However, which mechanism it is based on is related to such factors as the structure of haloalkane, and properties of leaving group, nucleophilic reagent and solvent.
Influences of halogen: No matter which mechanism the nucleophilic substitution reaction is based on, the leaving group always leave the central carbon atom with electron pair. This is just the opposite of the situation that nucleophilic reagent attacks the central carbon atom with electron pair. Therefore, the weaker the alkalinity of leaving group is, the more stable the anion formed is and it will be more easier for the leaving group to leave the central carbon atom; that is to say, the reactant is more easier to be substituted. The alkalinity order of halogen ion is I− < Br− < Cl− < F− and the order of their leaving tendency should be I− > Br− > Cl− > F−. Therefore, in four halides with the same alkyl and different halogens, the order of substitution reaction rate is RI > RBr > RCl > RF. In addition, if the leaving group is very easy to leave, many carbocation intermediates are generated in the reaction and the reaction is based on SN1 mechanism. If the leaving group is not easy to leave, the reaction is based on SN2 a mechanism.
Influences of solvent polarity: In SN1 reaction, the polarity of the system increases from the reactant to the transition state, because polar solvent has a greater stabilizing effect on the transition state than the reactant, thereby reduce activation energy and accelerate the reaction. In SN2 reaction, the polarity of the system generally does not change from the reactant to the transition state and only charge dispersion occurs. At this time, polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate (SN1) of tertiary chlorobutane in 25℃ water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24). The reaction rate (SN2) of 2-bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. In a word, the level of solvent polarity has influence on both SN1 and SN2 reactions, but with different results. Generally speaking, weak polar solvent is favorable for SN2 reaction, while strong polar solvent is favorable for SN1 reaction, because only under the action of polar solvent can halogenated hydrocarbon dissociate into carbocation and halogen ion and solvents with a strong polarity is favorable for solvation of carbocation, increasing its stability. Generally speaking, the substitution reaction of tertiary haloalkane is based on SN1 mechanism in solvents with a strong polarity (for example, ethanol containing water).
Nucleophilic substitution will be fastest in case of ______.
A primary alkyl halide would prefer to undergo ______.
Compound ‘A’ with molecular formula \[\ce{C4H9Br}\] is treated with aq. \[\ce{KOH}\] solution. The rate of this reaction depends upon the concentration of the compound ‘A’ only. When another optically active isomer ‘B’ of this compound was treated with aq. \[\ce{KOH}\] solution, the rate of reaction was found to be dependent on concentration of compound and \[\ce{KOH}\] both.
(i) Write down the structural formula of both compounds ‘A’ and ‘B’.
(ii) Out of these two compounds, which one will be converted to the product with inverted configuration.
How do polar solvents help in the first step in SN1 mechanism?
