When an alcohol and an aldehyde exist in the same compound, this compound is in equilibrium with what is called a " cyclic hemiacetal." The cyclic hemiacetal is favored when a 5- or 6- membered ring is formed. As shown below, this cyclic hemiacetal is formed via a new bond formation between the oxygen of the alcohol and the carbon of the C=O double bond. (We will look at this more specifically in Orgo II). H. 1 3 H G H 1) BH3-THF; 2) H₂O2, NaOH 1) 03; 2) DMS cold, dilute KMnO4,NaOH new bond formed 1) Hg(OAc)2, H₂O 2) NaBH4 1 With this in mind, which reagents will produce an alcohol from starting material G that will then cyclize to product cyclic hemiacetal H? O-H 5 4 3 a "cycli hemiacetal" H OH
When an alcohol and an aldehyde exist in the same compound, this compound is in equilibrium with what is called a " cyclic hemiacetal." The cyclic hemiacetal is favored when a 5- or 6- membered ring is formed. As shown below, this cyclic hemiacetal is formed via a new bond formation between the oxygen of the alcohol and the carbon of the C=O double bond. (We will look at this more specifically in Orgo II). H. 1 3 H G H 1) BH3-THF; 2) H₂O2, NaOH 1) 03; 2) DMS cold, dilute KMnO4,NaOH new bond formed 1) Hg(OAc)2, H₂O 2) NaBH4 1 With this in mind, which reagents will produce an alcohol from starting material G that will then cyclize to product cyclic hemiacetal H? O-H 5 4 3 a "cycli hemiacetal" H OH
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...
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