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IsoprophI bromide was treated separately...

IsoprophI bromide was treated separately with sodium ethoxide under two different conditions.
Reaction I:
Treatment of isopropyI bromide with `(Me_(3)CONa)` at `40^(@)C` gave almost exclusively compound `(A) (C_(3)H_(6))`.
Reaction II:
Treatment of `(i-PrBr)` with `NaOC_(2)H_(5)` at `30^(@)C` yileled compound `(A) (C_(3)H_(6))` along with a small amount of an ether `(B) (C_(5)H_(12)O)`.
Compound `(A)` was readily oxidised by a neutral solution of cold dil. `KMnO_(4)` to give a brown preciptate.
Which of the following most accureately repreasents the activated complex formed in reaction `(II)` that leads to compound `(A)` ?

A

B

C

D

Text Solution

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The correct Answer is:
To solve the question regarding the activated complex formed in reaction II that leads to compound A, we will follow a systematic approach. ### Step-by-Step Solution: 1. **Identify the Reactants**: - The reactant in reaction II is isopropyl bromide (i-PrBr) and sodium ethoxide (NaOC2H5). 2. **Understand the Reaction Conditions**: - The reaction is conducted at 30°C, which suggests that we are likely dealing with a reaction that can proceed via an elimination mechanism rather than substitution due to the presence of a strong base (NaOC2H5). 3. **Determine the Product**: - The product A is identified as an alkene (C3H6). Given that isopropyl bromide has two methyl groups, the likely alkene product is propene (C3H6). 4. **Mechanism of Reaction**: - The formation of compound A (alkene) from isopropyl bromide and sodium ethoxide suggests an E2 elimination mechanism. In this mechanism, the base (ethoxide ion) abstracts a proton from the β-carbon while the leaving group (bromine) departs from the α-carbon. 5. **Identify the Transition State**: - In the E2 mechanism, the transition state involves the simultaneous removal of a hydrogen atom and the departure of the bromine atom. This transition state can be depicted as having partial charges: the ethoxide ion will have a partial negative charge as it is abstracting a proton, and the bromine will have a partial negative charge as it is leaving. 6. **Draw the Transition State**: - The transition state can be represented with the isopropyl structure, showing the ethoxide ion attacking the hydrogen on the β-carbon, while the bromine is leaving. The transition state will have a partially formed double bond between the α and β carbons, and the ethoxide ion will be positioned close to the hydrogen being removed. 7. **Conclusion**: - Based on the above analysis, the activated complex formed in reaction II that leads to compound A can be accurately represented by the transition state structure that shows the ethoxide ion, the leaving bromine, and the developing double bond.

To solve the question regarding the activated complex formed in reaction II that leads to compound A, we will follow a systematic approach. ### Step-by-Step Solution: 1. **Identify the Reactants**: - The reactant in reaction II is isopropyl bromide (i-PrBr) and sodium ethoxide (NaOC2H5). 2. **Understand the Reaction Conditions**: ...
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IsoprophI bromide was treated separately with sodium ethoxide under two different conditions. Reaction I: Treatment of isopropyI bromide with (Me_(3)CONa) at 40^(@)C gave almost exclusively compound (A) (C_(3)H_(6)) . Reaction II: Treatment of (i-PrBr) with NaOC_(2)H_(5) at 30^(@)C yileled compound (A) (C_(3)H_(6)) along with a small amount of an ether (B) (C_(5)H_(12)O) . Compound (A) was readily oxidised by a neutral solution of cold dil. KMnO_(4) to give a brown preciptate. Which of the following is an accurate representations of compound (B) ?

IsoprophI bromide was treated separately with sodium ethoxide under two different conditions. Reaction I: Treatment of isopropyI bromide with (Me_(3)CONa) at 40^(@)C gave almost exclusively compound (A) (C_(3)H_(6)) . Reaction II: Treatment of (i-PrBr) with NaOC_(2)H_(5) at 30^(@)C yileled compound (A) (C_(3)H_(6)) along with a small amount of an ether (B) (C_(5)H_(12)O) . Compound (A) was readily oxidised by a neutral solution of cold dil. KMnO_(4) to give a brown preciptate. The formations of (A) and (B) are best explained by:

IsoprophI bromide was treated separately with sodium ethoxide under two different conditions. Reaction I: Treatment of isopropyI bromide with (Me_(3)CONa) at 40^(@)C gave almost exclusively compound (A) (C_(3)H_(6)) . Reaction II: Treatment of (i-PrBr) with NaOC_(2)H_(5) at 30^(@)C yileled compound (A) (C_(3)H_(6)) along with a small amount of an ether (B) (C_(5)H_(12)O) . Compound (A) was readily oxidised by a neutral solution of cold dil. KMnO_(4) to give a brown preciptate. Referring to Q. No. 67 which of the following represents the intermediate T.S for the formation of compound (B) ?

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