Question

Provide the organic product of the following reaction. 1) LiAIH(O-t-Bu 3,-7 oC 2) H20 Complete the electron-pushing mechanism for the reaction by adding any missing atoms, bonds, curved arrows, nonbonding electron pairs and charges. H Al O EO:

Answer 1

Benzoyl chloride is converted to its corresponding aldehyde Benzaldehyde (C.HSCHO) by reaction with Lithium tri-tert-butoxyaluminum hydride (LiAlH(O-t-Bu)) and water. Thus, the organic product of the reaction is Benzaldehyde (C.HSCHO). 1) LiAlH(0-t-Bu); -78 °C 2) H20 Benzoyl chloride Benzaldehyde Lithium tri-tert-butoxyaluminum hydride (LiAlH(O-t-Bu)) is a mild reducing agent which can reduce acid chloride to its corresponding aldehyde in a controlled way. Due to the presence of only one hydride ion to donate and bulky tert-butoxy groups (-(0-t-Bu)3), the reactivity of the reagent is mild and stops at the aldehyde stage. The electron-pushing mechanism for the reaction is as follows:

LiAIH(O-t-Bu), -78 °C བ་གནད་ མ་ 1: AVO-t-Bu) ས = 。-a(0-t-Bu) 5 Ai(0t-Bu)3 cl： - LiCI ：0 -A[0-t-Bu]， པ། - HH,0 + Al(0-t-Bua