a. The following is a real synthetic reaction published by the Burns lab at Stanfordtowards the synthesis of complex ‘ladderane' bacterial phospholipids. In thepresence of a copper triflate catalyst (not important for the question) and 254 nmlight, two major pericyclic products are formed at -4°C. List if each product isformed under thermal or photochemical conditions and show the relevantmolecular orbital for the electrocyclization reaction on the right side.HH5 mol%(CuOTf)2 C6H6-4 °C, C₂H6254 nmthermal (heat) orphotochemical (light)pericyclic reaction?37%ΗΗΗΗΗΗΗΗ42%relevant molecular orbital forelectrocyclization reaction:b. Draw a mechanism for the following [3,3] sigmatropic rearrangement.c. Use the starting ketone material on the left and any other reagents/solvents ofyour choosing to synthesize the ester molecule on the right. Number your chemicalsteps sequentially and please show intermediates after each step towards yourfinal product. You do not need to show mechanisms for this question.

The Q has 3 subparts, showing 3 reaction conditions Subpart a is the reaction of…

a. The following is a real synthetic reaction published by the Burns lab at Stanford towards the synthesis of complex 'ladderane' bacterial phospholipids. In the presence of a copper triflate catalyst (not important for the question) and 254 nm light, two major pericyclic products are formed at -4°C. List if each product is formed under thermal or photochemical conditions and show the relevant molecular orbital for the electrocyclization reaction on the right side. H 5 mol% (CuOTf) ₂ C6H6 -4 °C, C6H6 254 nm thermal (heat) or photochemical (light) pericyclic reaction? 37% ΗΗΗΗ HHHH 42% relevant molecular orbital for electrocyclization reaction: b. Draw a mechanism for the following [3,3] sigmatropic rearrangement. c. Use the starting ketone material on the left and any other reagents/solvents of your choosing to synthesize the ester molecule on the right. Number your chemical steps sequentially and please show intermediates after each step towards your final product. You do not need to show mechanisms for this question. ix

a. The following is a real synthetic reaction published by the Burns lab at Stanford towards the synthesis of complex 'ladderane' bacterial phospholipids. In the presence of a copper triflate catalyst (not important for the question) and 254 nm light, two major pericyclic products are formed at -4°C. List if each product is formed under thermal or photochemical conditions and show the relevant molecular orbital for the electrocyclization reaction on the right side. H 5 mol% (CuOTf) ₂ C6H6 -4 °C, C6H6 254 nm thermal (heat) or photochemical (light) pericyclic reaction? 37% ΗΗΗΗ HHHH 42% relevant molecular orbital for electrocyclization reaction: b. Draw a mechanism for the following [3,3] sigmatropic rearrangement. c. Use the starting ketone material on the left and any other reagents/solvents of your choosing to synthesize the ester molecule on the right. Number your chemical steps sequentially and please show intermediates after each step towards your final product. You do not need to show mechanisms for this question. ix

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

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

a. The following is a real synthetic reaction published by the Burns lab at Stanford
towards the synthesis of complex ‘ladderane' bacterial phospholipids. In the
presence of a copper triflate catalyst (not important for the question) and 254 nm
light, two major pericyclic products are formed at -4°C. List if each product is
formed under thermal or photochemical conditions and show the relevant
molecular orbital for the electrocyclization reaction on the right side.
H
H
5 mol%
(CuOTf)2 C6H6
-4 °C, C₂H6
254 nm
thermal (heat) or
photochemical (light)
pericyclic reaction?
37%
ΗΗΗΗ
ΗΗΗΗ
42%
relevant molecular orbital for
electrocyclization reaction:
b. Draw a mechanism for the following [3,3] sigmatropic rearrangement.
c. Use the starting ketone material on the left and any other reagents/solvents of
your choosing to synthesize the ester molecule on the right. Number your chemical
steps sequentially and please show intermediates after each step towards your
final product. You do not need to show mechanisms for this question.

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