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

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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
4
5 H
H
1) BH3-THF; 2) H₂O2, NaOH
1) 03; 2) DMS
cold, dilute KMnO4,NaOH
new bond formed
With this in mind, which reagents will produce an alcohol from starting material G that will then
cyclize to product cyclic hemiacetal H?
1) Hg(OAc)2, H₂O
2) NaBH4
4
O-H
3
a "cycli hemiacetal"
H
OH
Transcribed Image Text: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 4 5 H H 1) BH3-THF; 2) H₂O2, NaOH 1) 03; 2) DMS cold, dilute KMnO4,NaOH new bond formed With this in mind, which reagents will produce an alcohol from starting material G that will then cyclize to product cyclic hemiacetal H? 1) Hg(OAc)2, H₂O 2) NaBH4 4 O-H 3 a "cycli hemiacetal" H OH
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