(b) (i) Ethyl acetoacetate D is a versatile reagent for the synthesis of a wide range of ketones. Suggest reagents and conditions which could be used to convert D into E and F. D OEt E Ph Ph F (ii) Explain your chosen synthetic route to compound E with the aid of reaction mechanisms.

(b) (i) Ethyl acetoacetate D is a versatile reagent for the synthesis of a wide range of ketones. Suggest reagents and conditions which could be used to convert D into E and F. D OEt E Ph Ph F (ii) Explain your chosen synthetic route to compound E with the aid of reaction mechanisms.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter27: Biomolecules: Lipids

Section27.SE: Something Extra

Problem 15MP

See similar textbooks

Related questions

Q: Suggest a synthesis of the following alkene using a Wittig reaction strategy. Clearly draw the…

A: This compound wall be synthesized by using writting reaction.As we can see that the given alkene is…

Q: Draw the molecular orbital (MO) electron diagram for the Li2 molecular ion. Be sure your diagram…

A: The objective of this question is to explain the molecular orbital diagram of Li22-.

Q: (Thanks for the help if you can break down the steps and provide drawings(needed) during the answer…

A: The objective of the question is to understand the heme environment in oxymyoglobin and how the…

Q: An insulated container is used to hold 46.2 g of water at 32.5 \deg C. A sample of copper weighing…

A: The specific heat capacity for a given chemical substance or a solution refers to the amount of the…

Q: How will you synthesize 6-hepten-2-one starting from ethyl 3 - oxobutanoate ? Write the sequence of…

A: The question is based on the concept of organic synthesis.We need to synthesize the product using…

Q: 49. The figure is an anodic scan or a quiescent solution cyclic voltammetry experiment of a redox…

A: The purpose of this question is to show the

Q: Q4.2 A container, of volume 0.85 m³, has 500 g of an ideal gas at a temperature of 30°C and a…

A: The solution involves a series of mathematical calculations and conversions, and careful attention…

Q: QUESTION 12 What is the molarity of a solution of 10% by mass cadmium sulfate, CdSO 4 (molar mass =…

A: We have to find the molarity of a solution of 10% by mass cadmium sulfate (CdSO4)(molar mass=…

Q: Moody [1] studied the efficiency of a GC separation of 2-butanone on a dinonyl phthalate column.…

Q: OH 1) NaOH 2) Etl 1) xs EtMgBr 2) H₂O+ ? ?

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

Q: о N MYCH CO.H in hy EtoH

A: As we know that quinoline react with per acid form quinoline N oxide , then quinoline N oxide gives…

Q: i. ii. 111. Use the following data and Excel to plot a standard addition constant volume calibration…

A: The objective of this question is to show the plot of standard addition constant volune calibration…

Q: 55) What is the concentration of Cu2+ in the following cell at 25°C if the cell voltage is ¹253 V?…

A: The objective of the question is to find the concentration of Cu2+ in the given electrochemical cell…

Q: What are the products of the following reactions? Show all stereoisomers that are formed. Part A 1.…

A: The Gilman reagent, typically an organocopper compound, reacts with electrophilic carbon and form…

Q: A compound with two elements A and B has the cubic structure. A atoms are situated at the corners of…

Q: Suppose that the concentration of Cl- outside the cell is 10 and inside the cell is 100 mmol/liter.…

Q: - 5 solvolyzes 2x 10³ more rapidly in acetic acid than does 6. A -H CI 5 31 6 H -CI

A: The aim of this question is to show the chlorine in the axial position exhibits significantly faster…

Q: . which is generally not a component of a potentiometric measurement? voltmeter salt bridge…

A: The objective of the question is to identify the component that is generally not a part of a…

Q: (+) NH3 Br Na OH

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

Q: 2) Draw all constitutional isomers of C₂H8BN showing all atoms (zigzag structures are preferred but…

A: All constitutional isomers of C2H8BN

Q: Draw the initial organic product of the Bronsted acid-base reaction. Include all lone pairs and…

A: Alkenes has nucleophilic character hence, it can give electrophilic addition reaction. First of all…

Q: (i) Draw the chemical structure of the diazonium salt W. (ii) Draw the mechanism for the conversion…

A: . Chemical Structure of Diazonium Salt W:The diazonium salt is derived from the aniline molecule,…

Q: Control wells in the dopamine assay normally look like this: dopamine HVA neural cells Legend: =…

A: Dopamine is a neurotransmitter and is responsible to carry out many brain-related functions. Its…

Q: KMnO (C6H₁00) + (C₂H40₂) hot + (co₂)

A: We know KMnO4 is strong oxidising agent. will oxidise double bond to ketone and aldehy."

Q: The orbital occupancies for the d orbitals of several complex ions are diagrammed below. [Select]…

Q: Select the smaller member of each pair. a N or N³ ΟΝ ON³.

A: Ionic radii :- Ionic radii is the distance between the center of nucleus of ion and…

Q: Draw product OHC CHO

A: The given reaction is shown below.We have to predict the major product of the given reaction.

Q: (b) (c) Which of the following (B) and (C) will favour the enol form? Briefly explain your…

A: The aim of this question is to show the enol formation between b and c molecule. The enol form by…

Q: Step 4 C >97% ее ОН ОН

A: The given Synthesis show epoxidation formation by using Sharpless epoxidation by DET.

Q: In the glycogen structural diagram shown below, glycogen phosphorylase would be able to cleave…

A: The main aim of this question is to show the correct structure consists of alpha-1,4-glycosidic…

Q: 1. Answer ALL parts (a)-(c). (a) Answer BOTH parts (1) and (ii) (i) Predict the major product of the…

A: The objective of this question is to show the Nucleophilic addition reaction or epoxidation by MCPBA…

Q: estion 3: Which of the alkenes in Figure 3 can exist both as a cis and a trans mer? . А . в .с D…

A: Alkene can show geometrical isomerism .if they fullfill following conditions.

Q: Q5: Name the following compound A. m-Carboxyphenol C. 1-Carboxyphenol .CO2H OH B. o-Hydroxybenzoic…

Q: For the structures below, state whether the hydrogens marked Ha and H, are homotopic, enantiotopic…

A: A question based on introduction to organic chemistry. Three dimensional structures of two compounds…

Q: Consider the equilibrium shown below for an acid-base indicator: H+ + In HIn red yellow The K₂ for…

A: An indicator helps in visualizing the end point of the titration. It changes colour at the end…

Q: Draw the enantiomer of the following bicyclic carbonyl compound. Then draw a regioisomer. CH3 ОН

A: -> Enantiomers are pairs of molecules that are non-superimposable mirror images of each other.…

Q: Select the option showing a chair conformation with all Hydrogen atoms in the equatorial position.…

A: We have to find out the chair conformation with all H atoms in equatorial position.

Q: The carbon-14 decay rate of a sample obtained from a young tree is 0.251 disintegrations per second…

A: The given problem involves determining the age of an object based on the decay rates of two…

Q: How many of the following will undergo a favourable rearrangement to a lower energy carbocation? Me

Q: You have 0.100 M solutions of acetic acid (pKa = 4.76) and sodium acetate. If you wanted to prepare…

A: To prepare a buffer solution with a pH of 4.00 using acetic acid (CH3COOH) and sodium acetate…

Q: For each of the following compounds, draw three-dimensional (perspective) diagrams of the…

A: The aim of this question is to explain the enantiomers in three dimensions helps visualize their…

Q: R' O= N₂ R

A: The objective of this question is to show the nomenclature of given molecule. It is done by using…

Q: Give IUPAC names for the following compounds: CI O CH3CHCH₂CH₂CN(CH₂CH3)2 O || CH3OCCH₂CH₂COCH3

A: The objective of this question is to show the iupac nomenclature of the compound. It contain…

Q: Determine the lowest energy allowed absorption transition of carbon to El or E2. Justify your…

A: Let's break down the problem step by step.1. Russell-Saunders Coupling Scheme:The Russell-Saunders…

Q: 6. The general expression for the density of quantum states D(e) as a function of energy & under…

A: The objective of the question is to find the density of states for a two-dimensional quantum system…

Q: مند HIC OH OH CH3 CH3

A: The purpose of this question is to determine the iupac nomenclature of given' molecule.

Q: e. OH 1) NaOH 2) Etl 1) xs EtMgBr 2) H.Q+ ? ?

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

Q: What is the primary role of a catalyst in a chemical reaction? A) To increase the reactants'…

A: Catalyst never consumed in a chemical reaction.

Q: Standard Addition Variable Volume Calibration Curve i. Use the following data and Excel to plot a…

A: Given that:V= Total volume (volume of standard + sample)Vs= Volume of standard addedVo= Initial…

Q: What is the product: A) B) C) (CH₂=CH)₂CuLi ether 0= D) OH

A: Given acid chloride and reagent in ether solvent. Determine the product.

Concept explainers

Aldehydes and Ketones

Aldehydes and ketones are organic compounds that have a carbonyl group, C = O, as their functional group. They both differ in the placement of this carbonyl group in their structures.

Question

(b)
(i)
Ethyl acetoacetate D is a versatile reagent for the synthesis of a wide
range of ketones. Suggest reagents and conditions which could be used to
convert D into E and F.
D
OEt
E
Ph
Ph
F
(ii) Explain your chosen synthetic route to compound E with the aid of reaction
mechanisms.

Expert Solution

This question has been solved!

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

SEE SOLUTION Check out a sample Q&A here

Step 1: Introduction

VIEW

Step 2: Synthesis of Compound E:

VIEW

Step 3: Reaction Mechanism:

VIEW

Step 4: Synthesis of Compound F

VIEW

Solution

VIEW

Step by step

Solved in 5 steps with 1 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

(i) The enolisation of ketone A can generate an equilibrium mixture of A and either enol B or enolate C. Give the structure of both B and C, and the mechanism for their formation from A under the given conditions. (ii) A HCI (cat.) NaOH (cat.) B с Draw the structure of the product obtained when A is dissolved in D3O*. Give a detailed mechanism to account for the structure you propose.
(v) Compound K can be synthesised in excellent yield via a Robinson annulation between a,ß- unsaturated ketone H and ketone J. Provide detailed reaction mechanisms to account for the formation of product K. H KOH EtOH K
(iii) Rank the carbonyl compounds given below in terms of their relative reactivity with sodium borohydride. RT R CH3 CI (iv) Suggest two factors which combine to make the aldehyde react with sodium borohydride at a different rate from the ketone. (v) Based on electronegativity one might assume that the ester and acid chloride possess similar reactivity towards nucleophiles. Suggest why this turns out not to be the case (your answer should mention resonance and inductive effects).
(c) Treating lactone B with two equivalents of phenylmagnesium bromide, followed by hydrolysis in aqueous acid, gives a compound with the molecular formula C18H22O2, as shown below. Propose a structural formula for this compound. 1. PhMgBr (2 eq.) 2. H'/H>O C18H2202 bj 1o 14 10I f6 40 & 3 4 00 (8)
(b) A student wanted to synthesize methyl tert-butyl ether. He attempted the synthesis by adding sodium methoxide to tert-butyl chloride, but he obtained none of the desired product (1) (ii) Use an equation to show the product formed in this reaction Propose a suitable William ether synthetic route for methyl tert-butyl ether tach l.
Answer ALL parts. (a) Treatment of enone C with tetrabutylammonium fluoride leads to the formation of heterocycle D. 2 steps BU4NF C9H1602 A + B D OSIME,tBu (i) Enone C can be prepared from alkyne A and aldehyde B in two steps via a gold-catalysed reaction. Identify A and B and provide reagents/conditions for a synthesis of C. (ii) Give the structure of D and classify the ring-closing reaction for its formation from C according to Baldwin's rules (iii) Sketch the key molecular orbitals involved in the ring-closing reaction in part (ii) and hence explain whether the reaction is favourable or unfavourable.
(d) Propose a reaction mechanism to account for the following reaction. AIC3
Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)
(b) Suggest a reasonable biosynthesis for the naturally occurring alkaloid coniine (isolated from hemlock), starting from octanoic acid. Coniine
When N-bromosuccinimide is added to hex-1-ene in CCl4 and a sunlamp is shone on themixture, three products result.(a) Give the structures of these three products.(b) Propose a mechanism that accounts for the formation of these three products
(c) During Corey's synthesis of allomone he utilised the ketone shown below. OMe Outline the retrosynthesis to a monocyclic precursor.
(b) (c) Suggest a synthesis of the following compound (D) which utilises a conjugate addition strategy. Explain your reasoning clearly by drawing the mechanism. D Ph3P Me Predict the product and provide a mechanism for each of the following transformations; (i) H