The missing compounds A through G are to be supplied. Concept introduction: Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde . Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH 4 to produce D. PBr 3 then converts the -OH group to Br to produce E . The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

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Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

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