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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 is an accurate representations of compound `(B)` ?

A

MeOMe`

B

`Et-O-Et`

C

`i-Pr-O-Et`

D

`EtOMe`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the reactions of isopropyl bromide with sodium ethoxide under two different conditions and determine the structure of compound B. ### Step-by-Step Solution: 1. **Identify Isopropyl Bromide Structure:** - Isopropyl bromide (i-PrBr) has the structure: \[ \text{(CH}_3\text{)}_2\text{CHBr} \] - This means it has a bromine atom attached to a carbon that is also bonded to two other methyl groups. 2. **Reaction I:** - Isopropyl bromide is treated with \( \text{(Me}_3\text{C)Na} \) at \( 40^\circ C \). - This reaction likely leads to the formation of compound A, which is \( \text{C}_3\text{H}_6 \). - Given the conditions, this reaction favors elimination (E2 mechanism) leading to the formation of propene (C3H6). 3. **Reaction II:** - In this reaction, isopropyl bromide is treated with sodium ethoxide (\( \text{NaOC}_2\text{H}_5 \)) at \( 30^\circ C \). - This reaction yields compound A (C3H6) and a small amount of compound B (C5H12O). - The sodium ethoxide acts as a nucleophile and can perform an \( \text{S}_N2 \) reaction. 4. **Mechanism of Reaction II:** - The ethoxide ion (\( \text{C}_2\text{H}_5\text{O}^- \)) attacks the carbon attached to bromine, leading to the formation of an ether. - The bromine leaves as \( \text{NaBr} \), and the ethoxide group attaches to the isopropyl group. - The product formed will be isopropyl ethyl ether, which has the molecular formula \( \text{C}_5\text{H}_{12}\text{O} \). 5. **Identify Compound B:** - Compound B is the ether formed from the reaction, which is isopropyl ethyl ether. - The structure can be represented as: \[ \text{(CH}_3\text{)}_2\text{CHOCH}_2\text{CH}_3 \] - This matches the molecular formula \( \text{C}_5\text{H}_{12}\text{O} \). 6. **Conclusion:** - The accurate representation of compound B is isopropyl ethyl ether, which corresponds to option C in the provided choices. ### Final Answer: - The accurate representation of compound B is isopropyl ethyl ether, which corresponds to option C.

To solve the problem, we need to analyze the reactions of isopropyl bromide with sodium ethoxide under two different conditions and determine the structure of compound B. ### Step-by-Step Solution: 1. **Identify Isopropyl Bromide Structure:** - Isopropyl bromide (i-PrBr) has the structure: \[ \text{(CH}_3\text{)}_2\text{CHBr} ...
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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. 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. Which of the following most accureately repreasents the activated complex formed in reaction (II) that leads to compound (A) ?

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) ?

An optically active compound H(C_(5)H_(6)O) on treatment with H_(2) in the presence of Lindlar's catalyst gave a compound I (C_(5)H_(8)O) . Upon hydrogenation with H_(2) and Pd/C, Compound H gave J (C_(5)H_(12)O) . Both I and J were found to b optically inactive. Select the correct statements.

A compound X of formula C_(3)H_(8)O yields a compound C_(3)H_(6)O , on oxidation. To which of the following classes of compounds could X being

Reduction of hexose A (molecular formula C_(6)H_(12)O_(6) ) with sodium borohydride gives compound B and C. Compound B is optically inactive, whereas compound C is optically active. Which of the following is compound A?

Optically active isomer (A) of (C_(5)H_(9)Cl) on treatment with one mole of H_(2) gives an optically inactive compound (B) compound (A) will be :

Compound 'A' with the formula C_(3)H_(8)O on vigorous oxidation produces an acid C_(3)H_(6)O_(2) . 'A' is

Compound (A) C_(5)H_(8)O_(2) liberated CO_(2) on reaction with sodium bicarbonate. It exists in two forms neither of which is optically active. It yielded compound (B) C_(5)H_(10)O_(2) on hydrogenation. Compound (B) can be separated into enantiomorphs. Write structures of (A) and (B).

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  3. Compound (H) is:

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  4. The compounds (I) and (J) are respectively:

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  8. Compound (E) is:

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  9. Compound (F) is:

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