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कर्नाटक बोर्ड पी.यू.सी.पीयूसी विज्ञान 2nd PUC Class 12

Which compound in the following pair will react faster in SN2 reaction with OH−? CH3Br or CH3I

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प्रश्न

Which compound in the following pair will react faster in SN2 reaction with OH?

CH3Br or CH3I

लघु उत्तर
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उत्तर

In the SN2 mechanism, the reactivity of halides for the same alkyl group increases in the order. This happens because, as the size increases, the halide ion becomes a better leaving group.

R−F << R−Cl < R−Br < R−I

Therefore, CH3I will react faster than CH3Br in SN2 reactions with OH.

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  या प्रश्नात किंवा उत्तरात काही त्रुटी आहे का?
पाठ 6: Haloalkanes and Haloarenes - Exercises [पृष्ठ १९०]

APPEARS IN

एनसीईआरटी Chemistry Part 1 and 2 [English] Class 12
पाठ 6 Haloalkanes and Haloarenes
Exercises | Q 6.9 (i) | पृष्ठ १९०
नूतन Chemistry [English] Class 12 ISC
पाठ 6 Haloalkanes and Haloarenes
VERY SHORT ANSWER TYPE QUESTIONS | Q 33. (a) | पृष्ठ ६०९

संबंधित प्रश्‍न

Out of , which is more reactive towards SN1 reaction and why?


Which would undergo SN2 reaction faster in the following pair and why ?


Write the structure of the major organic product in the following reaction:

\[\ce{CH3CH2Br + KCN ->[aq{.} ethanol]}\]


What happens when methyl chloride is treated with KCN?


What is the action of the following on ethyl bromide
alcoholic solution of potassium hydroxide.


Which compound in the following pair reacts faster in SN2 reaction with OH?

  1. CH3Br or CH3
  2. CH3Cl, (CH3)3CCl

Which of the following is optically inactive?


Which of the following reactions is an example of nucleophilic substitution reaction?


The order of reactivities of the following alkyl halides for an SN2 reaction is:


Racemic compound has ____________.


The increasing order of nucleophilicity would be:


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


Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium? Give reason for your answer.


Which one is the correct order of nucleophilic strength (pKa) of following nucleophiles?


Among the following compounds I - IV, which one forms a yellow precipitate on reacting sequentially with (i) NaOH (ii) dil. HNO3 (iii) AgNO3?

I II III IV

Retention of configuration is observed in ______.


Convert bromoethane to propanamine.


The following questions are case-based questions. Read the passage carefully and answer the questions that follow:

Nucleophilic Substitution:
Nucleophilic substitution reaction of haloalkane can be conducted according to both SN1 and SN2 mechanisms. SN1 is a two-step reaction, while SN2 is a single-step reaction. For any haloalkane, which mechanism is followed depends on factors such as the structure of haloalkane, properties of leaving group, nucleophilic reagent and solvent.

Influences of solvent polarity:
In SN1 reaction, the polarity of the system increases from the reactant to the transition state, because a polar solvent has a greater effect on the transition state than the reactant, thereby reducing activation energy and accelerating 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, the 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 at 25°C in 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. Hence the level of solvent polarity has an influence on both SN1 and SN2 reactions but with different results. Generally speaking, a weak polar solvent is favourable for SN2 reaction, while a strong polar solvent is favourable for SN1. Generally speaking, the substitution reaction of tertiary haloalkane is based on SN1 mechanism in solvents with a strong polarity (for example ethanol containing water).

Answer the following questions:

(a) Why racemisation occurs in SN1? (1)

(b) Why is ethanol less polar than water? (1)

(c) Which one of, the following in each pair is more reactive towards SN2 reaction? (2)

(i) CH3 – CH2 – I or CH3CH2 – Cl

(ii)

OR

(c) Arrange the following in the increasing order of their reactivity towards SN1 reactions: (2)

(i) 2-Bromo-2-methylbutane, 1-Bromo-pentane, 2-Bromo-pentane

(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3- methylbutane


Discuss SN2 mechanism of methyl bromide using aqueous KOH.


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