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What is the product of the reaction between 5-aminopentanal and H₂/NaBH₃/CN?

a) 5-amino-1-pentanol
b) 5-amino-1-pentanone
c) 5-aminopentanal remains unchanged
d) 5-amino-1-pentanamine

1 Answer

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Final answer:

The reaction between 5-aminopentanal and H₂/NaBH₃/CN results in the reduction of the aldehyde group to a primary alcohol while leaving the amine group unaffected, yielding 5-amino-1-pentanol.

Step-by-step explanation:

The reaction between 5-aminopentanal and H₂/NaBH₃/CN is a chemoselective reduction that would typically reduce an aldehyde to a primary alcohol, while not affecting the amine group. Sodium cyanoborohydride (NaBH₃/CN) is a mild reducing agent especially suited for this purpose in the presence of hydrogen (H₂). The amine group (-NH₂) is not reactive under these conditions. Thus, the product of this reaction would be a primary alcohol with the amine group still intact.

If we consider the structure of 5-aminopentanal, it contains a terminal aldehyde group and an amine group on the 5th carbon atom. Upon reduction, only the aldehyde group at the end of the chain will be reduced to an alcohol group (-OH). Therefore, the product is 5-amino-1-pentanol.

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