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Find the final product 'E' CH(2)OH-CH=...

Find the final product 'E'
`CH_(2)OH-CH=CH_(2)overset((i)OsO_(4))underset((ii)NaSO_(3)H)rarr(A)overset(KHSO_(4))rarr (B) overset(Zn-Hg//"conc. HCl")rarr (C ) overset(NBS//hv)underset(C Cl_(4))rarr (D ) overset((CH_(3))_(2)"CuLi")rarr (E )`

A

But - 2 - ene

B

But -1 - ene

C

Isopentene

D

Pen - 2 - ene

Text Solution

AI Generated Solution

The correct Answer is:
To find the final product 'E' from the given reaction sequence, we will go through each step systematically. ### Step 1: Reaction with OsO4 and NaSO3H The starting compound is CH₂OH-CH=CH₂. When this compound reacts with osmium tetroxide (OsO₄) in the presence of sodium bisulfite (NaSO₃H), it undergoes syn-dihydroxylation. This means that the double bond (C=C) will be converted into a diol (two hydroxyl groups will be added across the double bond). **Product A:** CH₂OH-CH(OH)-CH(OH) ### Step 2: Reaction with KHSO4 Next, the product A reacts with KHSO₄. This step involves dehydration (removal of water) to form an alkene. The hydroxyl groups will be converted back to a double bond. **Product B:** CH₂=CH-CHOH ### Step 3: Reaction with Zn-Hg and concentrated HCl The product B is then treated with zinc amalgam in the presence of concentrated HCl. This reaction reduces the carbonyl group (if present) and adds hydrogen across the double bond. **Product C:** CH₂=CH-CH₂ ### Step 4: Reaction with NBS in the presence of hv and CCl₄ Next, product C undergoes allylic bromination when treated with N-bromosuccinimide (NBS) in the presence of light (hv) and carbon tetrachloride (CCl₄). This results in the addition of a bromine atom to the allylic position. **Product D:** CH₂=CH-CH₂Br ### Step 5: Reaction with (CH₃)₂CuLi Finally, product D reacts with lithium diorganocopper reagent, (CH₃)₂CuLi. This reagent will replace the bromine atom with a methyl group through a nucleophilic substitution reaction. **Final Product E:** CH₃-CH=CH-CH₃ (Butyne) ### Summary of the Reaction Sequence: 1. CH₂OH-CH=CH₂ + OsO₄/NaSO₃H → CH₂OH-CH(OH)-CH(OH) (Product A) 2. Product A + KHSO₄ → CH₂=CH-CHOH (Product B) 3. Product B + Zn-Hg/HCl → CH₂=CH-CH₂ (Product C) 4. Product C + NBS/hv/CCl₄ → CH₂=CH-CH₂Br (Product D) 5. Product D + (CH₃)₂CuLi → CH₃-CH=CH-CH₃ (Final Product E) ### Final Answer: The final product 'E' is **Butyne** (CH₃-CH=CH-CH₃).
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