The following reaction is showing production of ester using esterification reaction of n-butanol with acetic acid. OH + CH3CO₂H + H₂O Typical procedure of this reaction: 37g butanol, 60g glacial acetic acid and 3drops of sulphuric acid (H2SO4) are mixed together. The reaction mixture is then poured into 250cm³ water. The organic layer is separated and washed again with water (100cm³), saturated NaHCO3 (25cm³) and more water (25cm³). The crude ester is then dried over anhydrous Na2SO4 (5g), and then distilled. The yield=40g (69%). MW: C=12 gmot', O=16 gmot¹, H=1 gmot¹ a) Estimate the atom economy of this reaction b) Calculate the amount of waste and E-factor for this reaction c) Compute the effective mass yield for this reaction. d) Estimate the reaction mass efficiency. e) Critically comment why there is discrepancy in the value for yield, E-factor, atom economy, reaction mass efficiency and effective mass yield. Which one do you suggest the best to represent the greenness state of this reaction.

The following reaction is showing production of ester using esterification reaction of n-butanol with acetic acid. OH + CH3CO₂H + H₂O Typical procedure of this reaction: 37g butanol, 60g glacial acetic acid and 3drops of sulphuric acid (H2SO4) are mixed together. The reaction mixture is then poured into 250cm³ water. The organic layer is separated and washed again with water (100cm³), saturated NaHCO3 (25cm³) and more water (25cm³). The crude ester is then dried over anhydrous Na2SO4 (5g), and then distilled. The yield=40g (69%). MW: C=12 gmot', O=16 gmot¹, H=1 gmot¹ a) Estimate the atom economy of this reaction b) Calculate the amount of waste and E-factor for this reaction c) Compute the effective mass yield for this reaction. d) Estimate the reaction mass efficiency. e) Critically comment why there is discrepancy in the value for yield, E-factor, atom economy, reaction mass efficiency and effective mass yield. Which one do you suggest the best to represent the greenness state of this reaction.

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

Similar questions

Starting with ethene give a suitable reaction scheme to convert it into Ethyl ethanoate in 4 steps
The acetoacetic ester synthesis, shown below, can be used to prepare 5-methyl-2-hexanone. Which one of the following alkyl bromides would be used in the synthesis? (1) NaOEt (1) NaOH H2O heat 5-methyl 2-hexano OEt (2) alkylbromide ? (2) H30" CH;CH,CHB1CH, А. СH),СHBr (CH,),CHCH,Br В. (CH),CHCH,CH,Br С. D.
CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…
In the Grignard reaction. The benzoic acid product (abbreviate PHCO2H) was separated from the impurity biphenyl (abbreviated Ph-Ph) through an extraction with aqueous NAOH which deprotonated benzoic acid and converted it into sodium benzoate (abbreviated PHCO2NA). After the Grignard reagent, phenylmagnesium bromide was mixed with CO2, it was mixed with additional ether and 6M H,SO4. This gave a two phase liquid mixture. What was dissolved in the top layer? Select all answers that are appropriate. There may be one or more. PHCO,H NaCI PHCO Na Ph-Ph PHCO,MgBr 00000
[References] H2O OH TsO. DMSO ÓH Chrysanthemyl tosylate Artemesia alcohol Yomogi alcohol Chrysanthemic acid occurs as a mixture of esters in flowers of the chrysanthemum (pyrethrum) family. Reduction of chrysanthemic acid to its alcohol, followed by conversion of the alcohol to its tosylate, gives chrysanthemyl tosylate. Solvolysis of the tosylate gives a mixture of artemesia and yomogi alcohols. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions :A H-A TH.
Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. CI OMe OMe OMe 'N' HN N CI. + НО, Chloroacetic acid (S)-Metolachlor 3 NH2 CI + MEOH OMe Acetone Methanol 2-Ethyl-6-methylaniline 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.
Ph3P-CHCH3 H₂C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. CH3 00 + The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an SN2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene X m CH3 The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C=C bond is precisely where the C=O bond was in the reactant and no isomers (other than E/Z isomers)…
The mechanism of the Fischer esterification was controversial until 1938, when IrvingRoberts and Harold Urey of Columbia University used isotopic labeling to follow thealcohol oxygen atom through the reaction. A catalytic amount of sulfuric acid was addedto a mixture of 1 mole of acetic acid and 1 mole of special methanol containing the heavy18O isotope of oxygen. After a short period, the acid was neutralized to stop the reaction,and the components of the mixture were separated.H2SO4OCH3 C O H CH3 O H CH3 C O CH3 H2OO18 + +(a) Propose a mechanism for this reaction.(b) Follow the labeled 18O atom through your mechanism, and show where it is found inthe products.(c) The 18O isotope is not radioactive. Suggest how you could experimentally determinethe amounts of 18O in the separated components of the mixture
draw the following reactions and label it properly 1. Esterification of benzoic acid with n-propyl alcohol and concentrated H2SO4. 2. Esterification of salicylic acid with n-propyl alcohol and concentrated H2SO4. 3. Esterification of acetic acid with n-propyl alcohol and concentrated H2SO4. 4.Reaction with neutral FeCl3 with acetic acid 5. Reaction with neutral FeCl3 with tartaric acid
IF esize this compound by the → t-butyl ethyl ether Show the steps necessary to synthesize this compound by a rignard reaction. Start with an alkyl halide; after that you can add any organic or inorganic compound. → 1-hexanol Consider the following compounds:
A student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.
Ilustrate the mechanism of the oxidation of 1-hexanol with Jones Reagent (H2CrO4). Please show how the aldehyde is form (hexanal) and then the carboxylic acid (hexanoic acid).