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The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because of
- a)in DMSO, reaction predominates over SN1
- b)E2 reaction is preferred over SN1 in DMSO
- c)E2 reaction is preferred over SN2 in DMSO
- d)fluoride ion is not solvated by DMSO
Correct answer is option 'B'. Can you explain this answer?
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The reaction of tertiary butyl chloride in water to yield tertiary but...
Polar aprotic solvents DMSO strongly favour E2 reaction giving isobutene product.
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The reaction of tertiary butyl chloride in water to yield tertiary but...
Explanation:
The reaction of tertiary butyl chloride with water to yield tertiary butyl alcohol can occur via two different mechanisms: SN1 (nucleophilic substitution) and E2 (elimination). The presence of NaF in water does not appreciably affect this reaction, indicating that the reaction is not influenced by the nucleophilicity of fluoride ion. However, when the reaction is performed in DMSO (dimethyl sulfoxide), the presence of NaF leads to rapid formation of isobutene. This can be explained by the following reasons:
1. Solvation of fluoride ion:
Fluoride ion (F-) is a relatively small and highly polarizable anion. In water, fluoride ion is solvated by water molecules through hydrogen bonding, which stabilizes the ion and reduces its reactivity. However, in DMSO, fluoride ion is not as effectively solvated as in water. DMSO is a polar aprotic solvent, meaning it does not have hydrogen bonding capabilities. Therefore, fluoride ion is less solvated in DMSO, leading to increased reactivity.
2. SN1 vs E2 reactions:
In the presence of water, the reaction of tertiary butyl chloride can proceed via an SN1 mechanism, where the chloride ion is first expelled to form a carbocation intermediate. This intermediate can then be attacked by water to yield tertiary butyl alcohol.
In DMSO, however, the E2 reaction is preferred over the SN1 reaction. The E2 reaction involves the simultaneous elimination of the chloride ion and a proton from an adjacent carbon, resulting in the formation of an alkene (isobutene in this case). The preference for E2 over SN1 in DMSO can be attributed to the basicity of DMSO, which can facilitate the deprotonation step necessary for the E2 reaction to occur.
3. Influence of NaF:
NaF is a source of fluoride ion (F-) and can enhance the reactivity of fluoride ion in the reaction mixture. In water, the presence of NaF does not significantly affect the reaction because the solvation of fluoride ion by water molecules is already sufficient to stabilize the ion. However, in DMSO, NaF can further increase the reactivity of fluoride ion by providing a larger concentration of fluoride ions in the reaction mixture. This enhanced reactivity promotes the E2 reaction over the SN1 reaction, leading to the rapid formation of isobutene.
Therefore, the correct answer is option B: E2 reaction is preferred over SN1 in DMSO.
The reaction of tertiary butyl chloride with water to yield tertiary butyl alcohol can occur via two different mechanisms: SN1 (nucleophilic substitution) and E2 (elimination). The presence of NaF in water does not appreciably affect this reaction, indicating that the reaction is not influenced by the nucleophilicity of fluoride ion. However, when the reaction is performed in DMSO (dimethyl sulfoxide), the presence of NaF leads to rapid formation of isobutene. This can be explained by the following reasons:
1. Solvation of fluoride ion:
Fluoride ion (F-) is a relatively small and highly polarizable anion. In water, fluoride ion is solvated by water molecules through hydrogen bonding, which stabilizes the ion and reduces its reactivity. However, in DMSO, fluoride ion is not as effectively solvated as in water. DMSO is a polar aprotic solvent, meaning it does not have hydrogen bonding capabilities. Therefore, fluoride ion is less solvated in DMSO, leading to increased reactivity.
2. SN1 vs E2 reactions:
In the presence of water, the reaction of tertiary butyl chloride can proceed via an SN1 mechanism, where the chloride ion is first expelled to form a carbocation intermediate. This intermediate can then be attacked by water to yield tertiary butyl alcohol.
In DMSO, however, the E2 reaction is preferred over the SN1 reaction. The E2 reaction involves the simultaneous elimination of the chloride ion and a proton from an adjacent carbon, resulting in the formation of an alkene (isobutene in this case). The preference for E2 over SN1 in DMSO can be attributed to the basicity of DMSO, which can facilitate the deprotonation step necessary for the E2 reaction to occur.
3. Influence of NaF:
NaF is a source of fluoride ion (F-) and can enhance the reactivity of fluoride ion in the reaction mixture. In water, the presence of NaF does not significantly affect the reaction because the solvation of fluoride ion by water molecules is already sufficient to stabilize the ion. However, in DMSO, NaF can further increase the reactivity of fluoride ion by providing a larger concentration of fluoride ions in the reaction mixture. This enhanced reactivity promotes the E2 reaction over the SN1 reaction, leading to the rapid formation of isobutene.
Therefore, the correct answer is option B: E2 reaction is preferred over SN1 in DMSO.
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The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer?
Question Description
The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer? for Class 12 2024 is part of Class 12 preparation. The Question and answers have been prepared according to the Class 12 exam syllabus. Information about The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer? covers all topics & solutions for Class 12 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer?.
The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer? for Class 12 2024 is part of Class 12 preparation. The Question and answers have been prepared according to the Class 12 exam syllabus. Information about The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer? covers all topics & solutions for Class 12 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer?.
Solutions for The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer? in English & in Hindi are available as part of our courses for Class 12.
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ample number of questions to practice The reaction of tertiary butyl chloride in water to yield tertiary butyl alcohol is not appreciably affected by dissolved NaF; in DMSO, however, NaF bring about rapid formation of isobutene. It is because ofa)in DMSO, reaction predominates over SN1b)E2 reaction is preferred over SN1 in DMSOc)E2 reaction is preferred over SN2 in DMSOd)fluoride ion is not solvated by DMSOCorrect answer is option 'B'. Can you explain this answer? tests, examples and also practice Class 12 tests.
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