ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
bartleby

Concept explainers

Question
Book Icon
Chapter 16.5, Problem 6P
Interpretation Introduction

Interpretation:

The absolute configuration at the chirality center in the diol obtained by dihydroxylation of trans-2-butene is to be determined when one of the chirality center has (R)-configuration.

Concept introduction:

The dihydroxylation is the addition of two hydroxyl groups to the double bond of an alkene to form a 1,2-diol.

The dihydroxylation of alkene is a syn- type of addition as both hydroxyl groups add to the double bond from the same side.

The osmium tetroxide reacts with alkene and forms a cyclic osmate ester. In the presence of an oxidizing agent, this ester forms a diol.

The stereochemistry of chiral center is predicted by assigning the absolute configuration to the molecule.

The absolute conjugation can be determined by assigning priority to the groups bonded to chirality center.

The priority order is decided by Cahn-Ingold-Prelog priority rules. If the order of priority of groups bonded to chirality center preceding 123 is clockwise, then the absolute configuration is (R), and if it is counterclockwise, then the absolute configuration is (S).

The cis alkene, on dihydroxylation, forms the meso compound in which both carbon atoms bonded to hydroxyl group have opposite absolute configuration.

The trans alkene, on dihydroxylation, forms a racemic mixture and both the carbon atoms in a diol that are bonded to hydroxyl group have same absolute configuration.

Blurred answer
Students have asked these similar questions
a. The first three lines of this procedure describe the reaction used to make compound 5b. In the fourth line, hexane and sodium bicarbonate are added. What organic lab technique is being used here?  b. What is the purpose of the Na2SO4?  c. What equipment would you use to “concentrate [a solution] under reduced pressure”?
When N,N-dimethylaniline is treated with bromine both the ortho and para products are observed. However when treated with a mixture of nitric acid and sulfuric acid only the meta product is observed. Explain these results and support your answer with the appropriate drawings *Hint amines are bases* N HNO3 H2SO4 N NO2 N Br2 N Br + N 8-8-8 FeBr3 Br
Draw a mechanism that explains the formation of compound OMe SO3H 1. Fuming H2SO4

Chapter 16 Solutions

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE

Knowledge Booster
Background pattern image
Chemistry
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
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning