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...

See similar textbooks

Related questions

Q: Each of the following reactions has been reported in the chemical literature. Predict the product in…

A: In organic chemistry, different functional groups show different reactivity. Some of the common…

Q: The natural product halomon could theoretically arise from another naturally occurring compound…

A: In the given reaction, myrcene reacts with 3 equivalent of Br-Cl to form halomon. Since there are 3…

Q: Can you answer the question and explain it? With the mechanism Only e and f

A: Diels Alder reaction : It is a [4+2] cycloaddition reaction which takes place in the presence of…

Q: Consider 3,4-dimethylpiperidine being subjected to the below reaction scheme: step 1) CH3I…

Q: Discuss the regioselectivity of the compound equation below, including in your answer the terms:…

Q: (A) For each of the following alkynes, show the products for hydrochlorination, bromination, Murcury…

A: Note- The given question is a multipart question, hence I solved first three questions according to…

Q: p) (1) Hg(OAc)2 Н.0 (q) (2) NaBH4 H,O

Q: The 2 + 2 cycloaddition with one suprafacial and one antarafacial interaction is allowed. Show this…

A: An addition reaction in which two or more unsaturated molecules combine and form a cyclic product is…

Q: Select the method that would be successful in producing the given product in good yield starting…

A: This transformation involves aromatic electrophilic substitution and oxidation.This reaction…

Q: Dimethyl azodicarboxylate takes part in a DielsAlder reaction as a dienophile. Write the structure…

A: The solution is given below -

Q: A2. Complete the following by drawing the structure of the main organic product(s) AB-AG for each…

Q: Br () H Pd on C (a) () NANO, HCI, 0-5 °C () CUCN NO2 KMno, (b) heat Pd(OAc), PPh, (c) -B(OH Na,Co,…

Q: Q3] Diethyl malonate was treated with 2 moles of NaH followed by reaction with 1,4-dibromo-2-butene…

A: Diethyl malonate was treated with 2 moles of NaH followed by reaction with 1,4-dibromo-2-butene. The…

Q: What would be the expected major product when cyclooctene reacts with Cl2 in aqueous solution with…

A: The answer to the following question is-

Q: 6. Predict the products of the following reactions. Include stereochemistry where appropriate (a)…

Q: Which of the molecules below would be the expected product for hydrobro (addition of HBr) of the…

A: Product of following reaction can be made by applying appropriate reaction mechanism.

Q: NH₂ Br₂ AlBr3 HNO3/H₂SO4 OH NH₂ Br₂ AlBr3 NO2 HNO3/H₂SO4

Q: NaOH H20

Q: Organotin compounds play a significant role in diverse industrial applications. They have been used…

Q: CH3 1. Hg(OAc)2, H₂O 2. NaBH4 1. LDA 2. PhCH₂Br ? ?

A: Here we are required to predict the product of the reaction

Q: ad ebried emgie medi ja 1) BH3 2) H₂O2, H₂O, NaOH TOVO Vitor

A: The reaction of alkenes with BH3 in the presence of peroxide, water, and sodium hydroxide produces…

Q: Ts H,C- S-CI ÓH only geometric isomer OO, (тCРВA) OCH,CH, i) NaH CH,0 CH,0 racemic racemic two…

A: Tosylation of alcohol by tosyl chloride in the presence of pyridine gives corresponding tosylated…

Q: Can you please check my work on the following ochem reaction scheme and let me know if it is correct…

A: We have to check the answer which is given in the question.

Q: Provide the products for the reactions shown below. Suggest a reasonable mechanism (show electron…

A: Step 1: Step 2: Step 3: Step 4:

Q: Indane can undergo free-radical chlorination at any of the alkyl positions onthe aliphatic ring.…

A: The possible monochlorinated products from the given free-radical chlorination of indane are shown…

Q: a. 1. LIAIH4 3. РСС 2. H3O* workup b. Br 1. Mg', Et,0 2. CO2 3. H3O* workup C. HO OMe OMe p-TSA…

A: Answer:

Q: For each of the reactions shown below, give the products as indicated. Clearly show all…

A: Since we only answer up to 3 sub-parts, we’ll answer the first 3. Please resubmit the question and…

Q: Draw structures for the thermodynamic products of the following reaction. Pay careful attention to…

A: Here, we have to draw the products of the given reaction & then identify the thermodynamic…

Q: Consider the reaction of two compounds ‘A’ and ‘B’ which could make two possible diastereomers ‘AB’…

Q: (b)

A: Since you have posted multiple questions, we can only answer the last one as mentioned by you.

Q: (c) Diels-Alder reactions are a highly effective way to synthesise stereospecifically fused cyclic…

Q: (a) Determine if the following reaction is likely to be SN1, SN2, E1 or E2, discuss your rationale…

A: Hello. Since your question has multiple parts, we will solve the first question for you. If you want…

Q: • PRACTICE PROBLEM 8.25 How would you modify the procedure given in Solved Problem 8.8 so as to…

A: Hydrogenation of alkynes is done using hydrogen and Ni2B (P-2) catalyst. syn-Addition takes place to…

Q: See attached image

A: Number the four groups attached to the central carbon atom. Higher the atomic number more would be…

Q: a) The following two cyclobutenes 4 and 5 can be opened to form diene structures thermally, however…

A: An electrocyclic ring opening reaction is that type of reaction in which one sigma bond of a ring…

Q: D. NH₂ 1. 2. CH3 HNO3 H₂SO4 ▶ OH + v *** A

A: The first reaction is , reaction of aniline with NaNO2, HCl produces phenol as a product. In this…

Q: Write complete equations (using structures) to the following sequence of reactions and give the…

Q: 20.50 For each of the following, identify the product (represented by A, B, and C) that would be…

A: Answer :---

Q: a) b) ô Y HBr peroxide Br₂ CC14 (1) BH3.THF (ii) H₂O₂, OH

A: As per the rules only the first three sub-parts are being answered. Please resubmit for the…

Q: Suggest an explanation for the fact that the order of reactivity of the halides toward…

A: The order of reactivity of halides towards n-butyl brosylate in acetone is determined by the nature…

Q: Organotin compounds play a significant role in diverse industrial applications. They have been used…

Q: 5e

A: -Br is good leaving group than the -Cl. And acetate anion is strong nucleophile and weak base Hence…

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.

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1: Examining the Question and its subparts

VIEW

Step 2: Establishing the concept and reaction for Q a

VIEW

Step 3: Establishing the concept and reaction for Q b

VIEW

Step 4: Establishing concept and reaction for Q c

VIEW

Solution

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 5 steps with 4 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

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

Indane can undergo free-radical chlorination at any of the alkyl positions onthe aliphatic ring.Once the products have been separated, what instrumental technique would be most helpful for determining the structures of all the dichlorinated products?
Please don't provide handwritten solution ....
Provide a reasonable synthetic strategy for the synthesis of a racemic mixture of (1R,2R) and (1S,2S)-2-bromo-1-methylcyclopentanol from the compound shown below... Provide the bond line structure for the major organic products obtained in each step of the proposed strategy
Can you answer the question and explain it? With the mechanism Only g and h and i
Predict major organic product(s) in each of the following reactions with the alkene pictured. Clearly indicate the major product and be sure and indicate any stereochemistry. H2O, Br2 KMNO4, KOH heat Cold KMN04/KOH 1) BH3/THF 2) H202, NaOH (аq) HI CI CO3H 1) Hg(O2CCH3)2 CH3OH 2) NaBH4 Cl2
Predict the product of the following Diels-Alder reaction. Make sure to indicate stereochemistry whereverapplicable.
Q2 The following Diels-Alder reactions have been used in industrial syntheses of pharmaceutical agents. Suggest structures for the products A -E and briefly explain your reasoning. a) A CHCO2H, 20 °С b) B Mco H3CO Toluene, 120 °C c) Lewis acid catalyst OCH3 + D 'BuO CH2CI2, -78 °C major minor d) PHCH20. E Xylene, 150 °C
Dienes, Aromaticity, EAS, NAS 1. Give a systematic name for each of the following structures. Indicate relevant stereochemistry if present. NH₂
Deuterium (D, or 2H) is an isotope of hydrogen with atomic mass=2. Deuterium can be introduced into organic compounds by using reagents in which hydrogen has been replaced by deuterium. Outline preparation of the following compounds from the same alkene using appropriate deuterium-containing reagents.
How would the molecular orbitals of cyclopenta-1,3-diene, the carbocation, carbanion, and the radical differ? Drawings would be appreciated! Thank you in advance.
3 a only please
Based on the given information. Need help drawing the structure of the zinc reagent formed from Et2Zn and ClCH2I that allows for the ultimate formation of the cyclopropene ring.