Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. CI + ČOOET (Needed for the Ethyl acetoacetate synthesis of vitamin A) + HCI 2-Methyl-1,3-butadiene (Isoprene)

Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. CI + ČOOET (Needed for the Ethyl acetoacetate synthesis of vitamin A) + HCI 2-Methyl-1,3-butadiene (Isoprene)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.60P: Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A....

See similar textbooks

Related questions

Q: The compound obtained by treating propan-1-ol with PCC followed by excess of ethanol in presence of…

Q: . (a) Oxidation of 1-butanol with PCC will produce which of the following? 2-chlorobutanal…

A: PCC oxidation and Williamson ether synthesis

Q: 4 pts Provide the structure of the major organic product. in the following reaction sequence. 1.…

A: Answer:- This question is answered by using the simple concept of chemical reaction of ketone with…

Q: Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product.…

A: The reaction between isoprene and HCl is an addition reaction. The mechanism has been discussed…

Q: Identify compounds A and B, two synthetic intermediates in the 1979 synthesis of the plant growth…

A: Gibberellic acid induces cell division and elongation, thus making plants tall and leaves large.

Q: OH OH H2N Benzoie Acid Biphenyl Benzocaine Phenol benzocaine phenol biphenyl benzoic acid | dissolve…

A: The organic compounds present in the mixture are benzocaine, phenol, biphenyl and benzoic acid.

Q: Propanol plus phosphorous tribromide will yield __________. 1-bromopropane 1,1,1-tribromopropane…

Q: . In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask…

A: Explained as follows

Q: 6. Provide a synthesis for the molecule below showing all reagents and synthetic intermedate „CH3…

A: According to the question, we need to convert ethylbenzene to 4-chloro ethylbenzene.

Q: toluene n-butanol reflux Dean-Stark trap 2 hours но но 4a 5. 1a

Q: Introduction preparation of adipic acid from cyclohexanone and mechasim

A: cyclo hexanone is carbonyl compound (ketone) Cyclo hexanone oxidised into adpic acid in presence…

Q: 3. Suggest convenient methods of preparation of each of the following compounds from readily…

A: Interpretation - To prepare the each of following compounds which is given above in the question by…

Q: A retrosynthetic analysis of 1 was undertaken suggesting a forward synthesis starting from compounds…

A: Epoxides can be converted to aminoalcohols by the reaction of epoxide directly with ammonia or first…

Q: Discuss three methods that can be utilised to synthesise n – heptane in the laboratory

A: We’ll answer the first question since the exact one wasn’t specified. Please submit a new question…

Q: Predict the product for the following reactions using 2,4-Dinitrophenylhydrazine Test (letter i.)…

Q: constriction of bronchial tubes. Cromolyn sodium is synthesized in the above series of steps. 1.…

A: In any reaction bond making and breaking takes place and move ment of electron is found .

Q: OH pyridine 1. SOCI, SO2 Br DMSO / H20 2. N-Br OH N-H a = Proton transfer d = El Elimination f = Syl…

Q: What is the predicted product of the reaction shown? SOCI2 pyridine ОН

A: Given,

Q: . ammoniacal AgNO₃ which will match and quickly differentiate the compounds in the ff: 1.…

A: The question is based on the concept of organic reactions. we have to identify which of the given…

Q: o synthesize trans-cinnamic acid from benzaldehyde (PhCHO) and acetic anhydride (Ac2O) under basic,…

A: Chemical reaction with arrow pushing mechanism :

Q: Arrange the compounds in order of INCREASING reactivity towards bromination. I. Toluene,…

A: Benzene ring under go electrophilic substitution reactions Activating groups increase reactivity…

Q: Treatment of a carboxylic acid with triflwergacetic anhydride leads to an unsymmetrical anhydride…

A: unsymmetrical anhydride and ester are formed by reaction of nucleophilic addition to carbonyl group.…

Q: POD 9: 02-10-21 Provide the Stepwise synthesis for the following transformation

A: In this transformation, from a saturated lower analog, saturated higher analog is formed. Thus it…

Q: c) Scheme 1 shows the retrosynthetic analysis of compound M to the precursors via Functional Group…

A: The given transformation can be done by following reagents A= 1)Mg/Ether, 2) CO2 3) H3O+ B= 1)…

Q: 16. Give the major product of mononitration of the compound. 17. -OCH3 Give the product of the…

Q: 2. Selectivity. Show the reaction intermediates obtained after each step and the major product…

A: The details explanation of the organic reaction is given below

Q: Suggest a synthetic strategy for the synthesis of 6-methyl-3-heptanol from 4-methylpentanenitrile,…

Q: Show the product of treating y-butyrolactone with reagent.

A: Lactones are esters formed by various organic acids which are cyclic in nature. Gamma lactones are…

Q: OMe OMe

Q: What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence of steps? 1. Mg,…

Q: Reaction of (Z)-methyl-3-hexene with H2O/H2SO4 produces 3-methyl-3-hexanol (75% yield) 1. Write a…

A: We have given that Reaction of (Z)-methyl-3-hexene with H2O/H2SO4 produces 3-methyl-3-hexanol.…

Q: When CO2 is bubbled through a solution of benzyl magnesium bromide, and the mixture is then…

A: Grignard reagent react with carbondioxide carboxylic acid formed.

Q: но 3 но но Tamoxifen

A: Reagents and reaction conditions for each step

Q: propose a retrosynthetic analysis for the following molecules HO 4-chloro-6-methoxyquinazolin-7-ol…

A: The retrosynthesis of the given compounds are :

Q: Acid-catalyzed hydrolysis of HOCH2CH2C(CH3)2CN forms compound A (C6H10O2). A shows a strong peak in…

A: The formula for given compound is C6H10O2. The DBE for this compound is calculated in order to…

Q: A retrosynthetic analysis of 1 was undertaken suggesting a forward synthesis starting from compounds…

A: We have to synthesize organic compound 1 :

Q: OH NH, N2CI Anhydrous ZnCl2 NANO2 + HCI + NH, 300°C 0°-5°C Phenol aniline 1-chloro-2-phenyldiazene…

A: Please show the electron-flow mechanism of the general synthesis of Benzyl Chloride from Phenol.…

Q: How to prepare isoamyl 4-methoxycinnamate (bp 170°C) using basic glassware. state (i) the reactants,…

A: Using fundamental steps of synthesis of organic molecules via steps , reagent , purification etc.

Q: Synthesis of 1-bromobutane from 1-butanol (11 mL) – N-butanol (7.4 mL) – Sulfuric acid Give the…

Q: When diethyl succinate (1) is treated with NaOEt in EtOH, the major product is diethyl…

Q: . explain each step with words on how to get the structure. Step 1: Calculate the Index of…

Q: 6. Propose a route to Compound 2 from only bromobenzene and methyl formate as carbon sources, plus…

A: Let us talk about the grignard reagent. Here firstly the bromobenzene is used. The we have to…

Q: The sex pheromone of the common house fly has the molecular formula C23H46. It can be synthesized…

A: Concept revision: 1. We know hydrogen atom of terminal alkynes is acidic and can be abstracted by…

Q: 10-Bromo-a-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from…

Q: 4 Suggest the retrosynthetic analysis of Decane CH-(CH))s-CHs

A: It is a technique ofchemical synthesis by involving deconstructing a target molecule into readily…

Q: a O of d y 3. Suggest convenient methods of preparation of each of the following compounds from…

A: Concept behind synthesis of above four compound a) 1-indanone synthesis from dihydrocinnamic acid…

Q: -NH, ) from toluene( -CH, 6. Outline a synthesis of aniline ( ) using any necessary inorganic…

A: 1. Toluene is oxidized to benzoic acid using KMnO4. Benzoic acid is converted into benzoyl chloride…

Question

Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate

Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of
vitamin A.
CI
+
ČOOET
(Needed for the
Ethyl acetoacetate
synthesis of
vitamin A)
+ HCI
2-Methyl-1,3-butadiene
(Isoprene)

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

The vitamin A precursor has to be synthesised.

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 2 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

1. Discuss three methods that can be utilised to synthesise n – heptane in the laboratory 2. Outline the processes you would adopt to purity and test the purity of sodium benzoate, an active ingredient of most cosmetic products in the laboratory 3. The reaction of (Z)-3-Methyl-3-hexene with H2O/H2SO4 produces 3 – Methyl-3-hexanol (75 % yield)(a) Write a balanced chemical equation for the reaction (b) Propose a mechanistic explanation for the reaction
Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.
Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.
(a) Arrange the following compounds in an increasing order of their indicated property :(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)(b) How would you bring about the following conversions :(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde(iii) Bromobenzene to 1-phenylethanol
The following scheme shows the retrosynthetic analysis of 1-isopentylaziridine to form series of intermediates via Functional Group Inversion (FGI). Choose the correct reagents of N-S for the respective conversion
The compound obtained by treating propan-1-ol with PCC followed by excess of ethanol in presence of dry HCl(g) is: propanoic acid 1,1-Diethoxypropane 1-methoxypropan-1-ol Propylethanoate
A Grignard reaction of phenylmagnesium bromide with 3-pentanone gives 3-phenylpentan-3-ol as the major product. The crude product contains the 3-phenylpentan-3-ol product, unreacted 3-pentanone, and biphenyl (a side product). A developing solvent is found that separates the mixture into three spots on a silica gel TLC plate. Considering the functional groups present, predict which compounds would have the smallest and largest Rf values. Briefly justify your answer.
A. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.
E. TESTS FOR PHENOLIC COMPOUNDSPhenolic compounds such as phenol, salicylic acid, etc., give characteristiccolors with FeCl3 and Millon’s Reagent.1. Ferric Chloride TestAdd 5 drops of FeCl3 solution to 4 different test tubes containing 1 mL each ofdilute solutions of the following compounds and note the color obtained.a. Phenol _______________________________________________________________b. Salicyclic acid ___________________________________________________________c. Resorcinol _______________________________________________________________d. Picric acid _______________________________________________________________2. Millon’s TestPrepare another set of 4 test tubes containing 1 mL each of the solutions listedbelow. Add 3 drops of Millon’s reagent to each and place all the test tubes in aboiling water bath. Note the color formed.a. Phenol _______________________________________________________________b. Salicylic acid ___________________________________________________________c.…
(a) How will you carry out the following conversions?(i) Acetylene to Acetic acid (ii) Toluene to m-nitrobenzoic acid(iii) Ethanol to Acetone(b) Give reasons :(i) Chloroacetic acid is stronger than acetic acid.(ii) pH of reaction should be carefully controlled while preparing ammonia derivatives of carbonyl compounds.
Develop a synthetic strategy for 1-phenylpropyne from ethyl benzene.Start by writing the retrosynthesis analysis and then write the reactions as needed.
The pKas of chemicals HX and HY are 5 and 7 respectively. The pKa of carbonic acid H2CO3is 6. If you made up an ether solution of chemicals HX and HY in a separatory funnel, andthen added an aqueous solution of sodium bicarbonate NaHCO3 to that separatory funnel,would both HX and HY stay in the ether layer? Or would either or both of them transfer intothe aqueous layer? If one goes into the water layer, will it be in it’s neutral HX/HY form, or init’s deprotonated anionic form?