5. The behaviour A and B below, on treatment with NaOAc/HOAc, show that A is hydrolysed 13 times faster than B. Kinetic studies show A is racemised under the conditions and a single product forms, while B gives a mixture of products with cis-C being the kinetic product. Account for these reaction outcomes by drawing "3 dimensional" pictures of the reacting conformations, and including the relevant orbitals. TSO A single enantiomer racemic NaOAc / ACOH ACO H B OTS NaOAc / AcOH H O OH cis - kinetically

5. The behaviour A and B below, on treatment with NaOAc/HOAc, show that A is hydrolysed 13 times faster than B. Kinetic studies show A is racemised under the conditions and a single product forms, while B gives a mixture of products with cis-C being the kinetic product. Account for these reaction outcomes by drawing "3 dimensional" pictures of the reacting conformations, and including the relevant orbitals. TSO A single enantiomer racemic NaOAc / ACOH ACO H B OTS NaOAc / AcOH H O OH cis - kinetically

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...

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

5. The behaviour A and B below, on treatment with NaOAc/HOAc, show that A is hydrolysed
13 times faster than B. Kinetic studies show A is racemised under the conditions and a
single product forms, while B gives a mixture of products with cis-C being the kinetic
product.
Account for these reaction outcomes by drawing "3 dimensional" pictures of the reacting
conformations, and including the relevant orbitals.
TSO
A
H
single enantiomer
racemic
NaOAc
/AcOH
ACO
H
B
OTS
NaOAc
/ AcOH
H
O
OH
cis - kinetically

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