Question 6.SSE.27: Identify (X), (Y) and (Z) in the following synthetic scheme ......
Identify (X), (Y) and (Z) in the following synthetic scheme and write their structures. Explain the formation of labeled formaldehyde (H_2C^*O) as one of the products when compound (Z) is treated with HBr and subsequently ozonolysed. Mark the C^* carbon in the entire scheme.
BaC ^* O _3+ H _2 SO _4 \rightarrow( X ) \text { gas }(Here C^* denotes C^{14} )
CH_2 = CH – Br \overset{\text { (i) } Mg \text { / ether, (ii) X (iii) } H _3 O}{\xrightarrow {\hspace{2 cm}} } (Y) \overset{LiAlH_4}{\xrightarrow {\hspace{2 cm}} } (Z)[IIT, 2001]
Step-by-Step
BaCO _3+ H _2 SO _4 \rightarrow C ^* O _2 \uparrow \\ \quad \quad \quad \quad \quad \quad \quad \quad \quad \quad \text {(X)}
CH_2 = CHBr \overset{\text { (i) } Mg / \text { ether }}{\xrightarrow {\hspace{2 cm}} } CH_2 = CHMgBr \overset{\text { (ii) } C ^* O _2( X )}{\underset{\text { (iii) } H _3 O ^{-}}{\xrightarrow {\hspace{2 cm}} }} CH_2 = CHC^*OOH \overset{LiAlH_4}{\xrightarrow {\hspace{2 cm}} }
(Y)
Formation of C ^* H _2 O from (Z)
CH _2= CH \cdot C ^* H _2 OH \overset{ H ^{-}}{\longrightarrow} CH _2= CH _{+} \cdot C ^* H _2 \longleftrightarrow \\ C ^{+} H _2- CH = C ^* H _2 \quad \stackrel{ Br }{\longrightarrow} BrCH _2 \cdot CH = C ^* H _2 \stackrel{ O _3}{\longrightarrow} C ^* H _2= ORelated Answered Questions
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