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From the following sequence of reactions...

From the following sequence of reactions,
[A] `(C_(6)H_(12))overset(HCl)(to)(B)(C_(6)H_(13)Cl)+(C)(C_(6)H_(13)Cl)` react with `AgNO_(3)` to give white ppt.
[B] `overset(Alc. KOH)(to)` (D) (An isomer of A) gives positive test with `Br_(2)//C Cl_(4)`
[D] `overset("Ozonolysis")(to)` (E) gives positive iodoform test and negative Fehling's test .
[A] `overset("Ozonolysis")(to)(F)+(G)` both F and G give positive Tollen's test.
`[F]+[G]overset(Conc. NaOH)underset(Delta)(to)HCOONa+"alcohol"`
The structure of C is :

A

B

C

D

Text Solution

AI Generated Solution

The correct Answer is:
To determine the structure of compound C from the given sequence of reactions, we can follow these steps: ### Step 1: Analyze Compound A - **Given:** The molecular formula of A is \(C_6H_{12}\). - **Degree of Unsaturation:** \[ \text{Degree of Unsaturation} = \frac{(n + 1 - m)}{2} = \frac{(6 + 1 - 12)}{2} = \frac{-5}{2} = 1 \] This indicates that A has either one double bond or one ring. ### Step 2: Identify the Reaction of A with HCl - **Reaction:** \(A + HCl \rightarrow B + C\) - **Result:** B is \(C_6H_{13}Cl\). This indicates that A is likely an alkene, which reacts with HCl to form a chloroalkane. ### Step 3: Identify Isomers B and C - **Isomers:** Since B and C are both \(C_6H_{13}Cl\), they can be structural isomers resulting from the addition of HCl to A. ### Step 4: Analyze the Reaction of B with Alcoholic KOH - **Reaction:** \(B \xrightarrow{Alc. KOH} D\) - **Result:** D is an isomer of A and should also be an alkene. ### Step 5: Ozonolysis of D - **Reaction:** \(D \xrightarrow{Ozonolysis} E\) - **Result:** E gives a positive iodoform test and a negative Fehling's test, indicating that E is likely a methyl ketone. ### Step 6: Ozonolysis of A - **Reaction:** \(A \xrightarrow{Ozonolysis} F + G\) - **Result:** Both F and G give a positive Tollen's test, indicating they are aldehydes. ### Step 7: Identify the Products of F and G with NaOH - **Reaction:** \(F + G \xrightarrow{Conc. NaOH, \Delta} HCOONa + \text{alcohol}\) - **Result:** This indicates that F and G undergo a Cannizzaro reaction, which occurs in compounds without alpha hydrogens. ### Step 8: Determine the Structure of C - **Conclusion:** Since C is a product of the reaction of A with HCl, and considering the structure of A, we can deduce that C must be a chloroalkane that is a structural isomer of B. Given the reactions and tests, C is likely to be a primary or secondary alkyl chloride. ### Final Structure of C - The structure of C can be deduced to be a secondary or primary alkyl chloride based on the reactions and the fact that it gives a white precipitate with AgNO3 (indicating a good leaving group).
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