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EEJ MAIN Chemistry QUESTION #5572
Question 1
What is the major product when $R-C\equiv N$ is treated with (1) $AlH(i-Bu)_2$ (DIBAL-H), then (2) $H_2O$?
  • RCOOH
  • $RCONH_2$
  • RCHO✔️
  • $RCH_2NH_2$
Correct Answer Explanation
DIBAL-H (diisobutylaluminium hydride) at low temperature partially reduces a nitrile ($RC\equiv N$) to an imine intermediate ($RCH=NH$), which upon aqueous workup ($H_2O$) hydrolyses to give an aldehyde (RCHO). Full reduction with $LiAlH_4$ would give the amine $RCH_2NH_2$.