CHAPTER FIFTEEN Alcohols, Diols, and Thiols H-AIH H AlH RC=O Tetraalkoxyaluminate Addition of water converts the tetraalkoxyaluminate to the desired alcohol (R,CHO) 4H,0->4R CHOH Al(Od) Tetraalkoxyaluminate PROBLEM 15.2 Sodium borodeuteride(naBD) and lithium aluminum deuteride (LiAID) are convenient reagents for introducing deuterium, the mass 2 isotope of hydrogen, into organic compounds. Write the structure of the organic product of the following reactions, clearly showing the position of all the deuterium atoms in each p.264-266 (a)Reduction of CH3 CH (acetaldehyde)with NaBDa in H2O (b) Reduction of ch3CCH3(acetone) with NaBDa in CH3OD (c)Reduction of CHs cH( benzaldehyde)with NaBDa in CD3OH ( d)Reduction of HCH (formaldehyde) with LiAIDa in diethyl ether, followed by addition of d2O SAMPLE SOLUTION (a) Sodium borodeuteride transfers deuterium to the car bonyl group of acetaldehyde, forming a c-D bond CH3C=O CH3 O ->CH CHO)B he C-D bond formed in the preceding step while forming an o-H bonds Hydrolysis of (CH3 CHDO)4B in H2O leads to the formation of ethanol, retain CHH-o- B(OCHDCH2)3→→cH2cH+ OCHDCH2)2°3 CHaCHOH+BoHa Neither sodium borohydride nor lithium aluminum hydride reduces isolated car- bon-carbon double bonds. This makes possible the selective reduction of a carbonyl group in a molecule that contains both carbon-carbon and carbon-oxygen double bonds Back Forward Main MenuToc Study Guide ToC Student o MHHE WebsiteAddition of water converts the tetraalkoxyaluminate to the desired alcohol. PROBLEM 15.2 Sodium borodeuteride (NaBD4) and lithium aluminum deuteride (LiAlD4) are convenient reagents for introducing deuterium, the mass 2 isotope of hydrogen, into organic compounds. Write the structure of the organic product of the following reactions, clearly showing the position of all the deuterium atoms in each: (a) Reduction of (acetaldehyde) with NaBD4 in H2O (b) Reduction of (acetone) with NaBD4 in CH3OD (c) Reduction of (benzaldehyde) with NaBD4 in CD3OH (d) Reduction of (formaldehyde) with LiAlD4 in diethyl ether, followed by addition of D2O SAMPLE SOLUTION (a) Sodium borodeuteride transfers deuterium to the car￾bonyl group of acetaldehyde, forming a C±D bond. Hydrolysis of (CH3CHDO)4B  in H2O leads to the formation of ethanol, retaining the C±D bond formed in the preceding step while forming an O±H bond. Neither sodium borohydride nor lithium aluminum hydride reduces isolated car￾bon–carbon double bonds. This makes possible the selective reduction of a carbonyl group in a molecule that contains both carbon–carbon and carbon–oxygen double bonds. D  BD3 CH3C O H C O  D BD3 H CH3 3CH3CH O X (CH3CHO)4B  D HCH O X C6H5CH O X CH3CCH3 O X CH3CH O X Tetraalkoxyaluminate (R2CHO)4Al  Al(OH)4  Alcohol 4H2O 4R2CHOH 3R2CœO H AlH3  R2C O   AlH3  R2C O H Tetraalkoxyaluminate (R2CHO)4Al  586 CHAPTER FIFTEEN Alcohols, Diols, and Thiols CH3CH B(OCHDCH3)3 H OH D O  D OH CH3CH Ethanol-1-d 3H2O 3CH3CHOH D B(OH)4  OH B(OCHDCH3)3  An undergraduate labora￾tory experiment related to Problem 15.2 appears in the March 1996 issue of the Jour￾nal of Chemical Education, pp. 264–266. Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website