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

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
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
Expert Solution
steps

Step by step

Solved in 3 steps with 3 images

Blurred answer
Knowledge Booster
Alkynes
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY