Esterification of BenzocaineBy: Nick Makowski and Monica Schaeffer Purpose:To practice the techniques of refluxing and vacuum filtration to perform an esterification reaction to create benzocaine from p-aminobenzoic acid Chemical Structures/Reactions/Mechanisms: Results: Physical Appearances- & soln. It is also 0000006684 00000 n
Preparation of Methyl Benzoate. Draw the major organic product for the following reaction. Draw the major organic product for the following reaction: Draw the major organic product of the following reaction. )Z)<>y3+
?cJaYdf~?TXb%bFsd_0&0ckxH?a{G6b"fdi@Oc@sX hV|xCF + 0WLq Fischer Esterification of Benzoic Acid & Methanol in HCl (RXN Mechanism) - YouTube This video screencast was created with Doceri on an iPad. Vibration analysis was carried out to confirm TS structures and imaginary frequencies. Water can be removed by simple distillation or azeotropic distillation with different solvents. ezmkZdTI'24y[8XIU)bi6^h}iS`j2=2}A3St }3)3vT,CH`D^]"V>Nf'qHw}E]WOxh(g1$#Tj7W6L7JDE!6?,2_kU+GGdA CaCl 2 While separating the layers, it gauge when to close the stopcock perfectly, so that led to a loss of eventual product. First off, a small amount of the weighed benzoic acid did not make into the 100 mL round-bottomed flask. 0000010846 00000 n
So, does the ethoxide attack the carbonyl carbon or the CH2 of the ethyl group? collected in Erlenmeyer flask, The distillate collected has some white Draw the major product formed in the following reaction of an epoxide with methoxide in methanol. ?t"sh@,
W. Benzoic Acid from Ethyl. Why primary alcohols are used in Fischer esterification? HWKs0WgE$D%Cpszpu; !Nfo} @hqW8A!LtgWm]QH`
*qA`oVpDd@5a8*At[} ~.T? A: Given , Concentration of H2CrO4 =0.0150 M. Draw the major organic product for the reaction below. : an American History (Eric Foner), Fischer esterification of benzoic acid lab report. 0000008133 00000 n
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(Methyl Benzoate + Water) - YouTube A carboxylic acid (like benzoic acid) and an alcohol (like methanol) will form an equilibrium with an ester (in this case, methyl benzoate) and water.. Draw the major organic product formed in the following reaction. reactants was chosen because from the mechanism we can see that in the starting material 0000001303 00000 n
Draw the major organic product formed when the compound shown below undergoes a reaction with NaBH4. Porphyrin Esterification and Ester Hydrolysis The Esterification of Benzoic Acid by Mercaptans . And this is when the base-catalyzed ester hydrolysis turns to be more beneficial. Fischer esterification is an acid-catalyzed condensation of a carboxylic acid with an alcohol to form esters. The Fischer exterification technique is utilized in the academic and industrial settings due to the simplified synthesis and safety parameters of the overall reaction. However, they are corrosive chemicals and give the moderate yield of methylesters. 1) Nucleophilic Attack by the Alcohol. The reaction will be prepared by Fischer esterification, which involves the reaction reaching equilibrium after refluxing for a few hours. Learn about esterification and its mechanism. Video transcript. Organic Chemistry Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice Quizzes. Add to it 0.62 mol of methanol in a 100 mL round-bottomed flask. looks clear, As the cooled reaction mixture was product while shaking and releasing pressure during separation. 0000011487 00000 n
Draw structure for the product obtained from the reaction of beta-D-talopyranose with the reagents. If a chiral product is formed, clearly draw stereochemistry. Azeotropes can be distilled using a Dean-Stark trap. In the laboratory manual, they state that the Further, water must be removed as it is produced to shift the equilibrium towards ester formation, to increase the yield. We have a primary carbon and the acetate is not the worst leaving group certainly better than the ethoxide. The experimental procedure was followed pretty much as written. z@{[Qfp(Ukqxd45yIBU`!I)rW,XQRrf#M$N5S7ruK7> .T;kdViOD,xpsCF0#(x^gVEj0fZ[EDyNt'G|f }g Gd xc9XX}fh|A@S*F4ie1GP[%YyiSE+J.EbH:tHN3jJBsU7)W}J{0Is.`=fS5~ja|S?$ufYNA]eVD&t6PBIGbJh1N3$bo$c#^9)YKSc+;\vW% 0000002583 00000 n
Ester Hydrolysis: Acid and Base-Catalyzed Mechanism, Carboxylic Acids and Their Derivatives Practice Problems, Ester Hydrolysis by Acid and Base-Catalyzed Hydrolysis, Esters Reaction with Amines The Aminolysis Mechanism, Ester Reactions Summary and Practice Problems, Preparation of Acyl (Acid) Chlorides (ROCl), Reactions of Acid Chlorides (ROCl) with Nucleophiles, Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents, Reduction of Acyl Chlorides by LiAlH4, NaBH4, and LiAl(OtBu)3H, Preparation and Reaction Mechanism of Carboxylic Anhydrides, Amides Hydrolysis: Acid and Base-Catalyzed Mechanism, Amide Dehydration Mechanism by SOCl2, POCl3, and P2O5, The Mechanism of Nitrile Hydrolysis To Carboxylic Acid, Nitrile Reduction Mechanism with LiAlH4 and DIBAL to Amine or Aldehyde, The Mechanism of Grignard and Organolithium Reactions with Nitriles. 356 0 obj
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Draw the product and a complete mechanism for its formation, for the Fischer esterification of benzoic acid. separatory funnel, shake, and drain off decant the methyl benzoate into it. Draw the organic product(s) formed in the given reaction. b) Washing the organic layer with saturated sodium chloride solution makes the water Some esters can be prepared by esterification, a reaction in which a carboxylic acid and an alcohol, heated in the presence of a mineral acid catalyst, form an ester and water: The reaction is reversible. Draw the organic product for the reaction: CH_3CH_2CH_2OH + K_2Cr_2O_7 (aq) overset{H_2SO_4}{rightarrow}. Therefore, special methods are being used for the synthesis of esters by using tertiary alcohols. This is an important laboratory method for the synthesis of esters, which are widely used as flavorings, fragrances, rubber, and plastics. Esterification. Mechanism of acid-catalyzed Fischer esterification The mechanism of Fischer esterification is similar to acid-catalyzed reactions. In the presence of a small amount of water, this reaction shifts in the backward direction. Esters are made by the reaction of a carboxylic acid with an alcohol, a process that is called esterification. 20.20 (b) 1,4-Benzenedicarboxylic acid (terephthalic acid) is a compound with the formula C8H 6O 4that gives the indicated diol on treatment with LiAlH4followed by protonolysis. The typical and traditional method for the synthesis of carboxylic acid esters is the reaction of carboxylic acids with an excess amount of alcohols in the presence of a catalytic amount of H 2 SO 4 by using Dean-Stark apparatus [ 1, 2, 3 ], in which H 2 SO 4 catalyzes the addition of the alcohol to the carboxylic acid, and the H 2 O thus The carbonyl carbon of carboxylic acid can also get proton from the protonated alcohol. Some sources of error for this difference could have been 0000008969 00000 n
Also, draw what happens when the product of this step is treated with ethyl benzoate. How can we monitor the progress of a chemical reaction? Exp6 prepmethylbenzoate chem234 University Of Illinois. 0000006333 00000 n
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Draw a stepwise mechanism for the following organic reaction: draw the organic product of the following reaction. a. Butanol + NaOH/25^o C gives ? The reaction often involves an alcohol and a Bronsted acid (such as a carboxylic acid, sulfuric acid, or phosphoric acid ). 0000011809 00000 n
Draw the organic product for the following acid-catalyzed hydrolysis reaction. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. How can we increase the yield of the product? Consider the acid-catalyzed Fischer esterification reaction between ethanoic acid and ethanol. The method is equally convenient for esterification of a dicarboxylic acid 4, its anhydride, and chloro, iodo and nitro substituted aromatic carboxylic acids. The complete mechanism showing all intermediates and arrows to demonstrate electron movement. The purity of the benzoate will then be determined using infrared spectroscopy. hb```g``nf`e` ,@QVADeE*00et 9 ``HK XDQ:L,;X>(MpOwp``E Below is the reaction between benzoic acid, a carboxylic acid, and ethanol, an alcohol. Draw the organic product of the reaction of phenol with Br2 in the space below. {HMS#X$jlu`(v}bUjUU1D"NzZo^$UUPuL5][{}*D}a43jws B]h). The single experiment of benzoic acid esterification was started by charging the reactor with different loading of the catalyst, m = (2, 3 and 4) g and 50 mL of benzoic acid solution in methanol with an initial concentration, = 2 g L 1 (mole ratio benzoic acid : methanol = 1:1509). %PDF-1.6
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Ester conversions of 65 to 70% were achieved for all the catalysts under the best reaction conditions. 0000010510 00000 n
Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01, Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. Koehler), The Methodology of the Social Sciences (Max Weber), Psychology (David G. Myers; C. Nathan DeWall), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Civilization and its Discontents (Sigmund Freud), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. Draw a structure for the major organic product you would expect from reaction of 3-methyl-3-pentanol with HCl. 0
Draw the product of the organic reaction shown below. 4) Protonation of the carboxylate. Can anyone show me how to draw this? a cloudy white solid, Methyl benzoate is what is being The experiment was performed to isolate the product methyl benzoate and to separate out the unreacted benzoic acid, by the method of base extraction. 0000001060 00000 n
CH_3CH_2OH, H^+. Discussion/ Conclusion: %PDF-1.3
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!^\c5}]Fy!H- Draw the organic product formed in the below reaction. The reaction will be prepared by Fischer esterification, which involves the reaction reaching equilibrium after refluxing for a few hours. Why is the sulfuric acid necessary? Draw the organic product obtained from the Wittig reaction between cyclohexanone, triphenylphosphine, butyllithium, and 2-bromobutane. Draw the major organic product of the reaction. 15 9 Hydrolysis of Esters Chemistry . Draw the products of the following reactions. form an ester. 0000011182 00000 n
Such a reaction yields an ester that contains a free (unreacted) carboxyl group at one end and a free alcohol group at the other end. and opening the stopcock often. 54 Esterification of Substituted Benzoic Acid acids,7,8 ionic liquids,9,10 11,12or solid acid catalysts. By using Le Chateliers principle, we can shift the equilibrium toward reactants or products. 110 217 because a lot of pressure is produced in the reaction, and it must be released by inverting The partially positive carbon becomes susceptible to the attack of negatively charged species such as the oxygen atom of alcohols. Abstract A biotechnological route via enzymatic esterification was proposed as an alternative way to synthesize the problematic anti-oxidant eugenyl benzoate. The new method overcomes the well-known drawbacks of the chemical route in favor of a more sustainable reaction process. trailer
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Once benzoic acid is added to one end of the ethylene glycol, the remaining OH group is more active toward esterification. Createyouraccount. The hydrogen ion (H+) of alcohol is removed from the alcohol whereas hydroxide (OH) is removed from the acid to form water molecules. 0/mL of methanol x 25mL= 19 PET is used to make bottles for soda pop and other beverages. 0000050812 00000 n
please draw the reaction mechanisms: 2-chloro-2-methylpropane + AgNO3 in ethanol Bromocyclohexane + AgNO3 in ethanol. 2. Draw 2,4-dinitrophenylhydrazine and 2-butanone reaction mechanism. In this question , we have to show the mechanism of acid cataylsed esterification of benzoic acid with (S) -sec-butanol in the presence of catalytic amount of sulfuric acid . Here, the sulphuric acid acts as a catalyst which provides the proton to protonate the carboxylic acid as well as a dehydrating agent. 0000001123 00000 n
methyl ether, Add the t-butyl methyl ether to This gave me a percent yield of 18%. Legal. 0000012257 00000 n
typical yield for students is around 7g. Why we can not use tertiary alcohols for Fischer esterification? It consists of five steps as elucidated below: Protonation Nucleophilic addition Tautomerization Dehydration Deprotonation 1. Write the overall reaction for our esterification reaction, and its mechanism. v`g sh'[m e
H0S4"}A49d9U2R2XhL2"%2 ak>-sRHn1FsIJC*)3(ur~+A)71^EtTw!ym('dCrI Draw the ester that is formed from the reaction of benzoic acid and ethanol. This was proved by the isotope labeling experiment where methanol has an oxygen isotope (O18) treated with benzoic acid. l_2.K {H
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Esterification is the chemical reaction that results from the reaction of alcohol (ROH) and an organic acid (RCOOH) to produce an ester (RCOOR) and water. actual yield: 2, Percent yield: (Actual/ theoretical) x 100= (2.07g/11)100=18%. Lastly, if the concentration of methanol was higher, that would have also led to a higher percent yield. Cross), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Give Me Liberty! methyl benzoate is high, 199C. the water layer, With 25ml of water and 25ml of Draw the mechanism for the following organic reaction. How will this reaction be helpful in separating benzoic acid and piperazine using extraction? When a carboxylic acid reacts with an alcohol, it produces an ester. And that is the acid-catalyzed hydrolysis of esters containing a tertiary alkyl group: The products are a carboxylic acid and alcohol just as expected. 0000001236 00000 n
The process of esterification has been reported to greatly improve the hydrophobic property of starch by substituting the hydroxyl groups on each glucose residue thereby converting it to a hydrophobic ester group with reagents (organic and inorganic acids, and their derivatives). Acid-catalyzed carboxylic acid esterification and ester hydrolysis mechanism: acylium ion as a sharing active intermediate via a spontaneous trimolecular reaction based on density functional theory calculation and supported by electrospray ionization-mass spectrometry. 0000011641 00000 n
Introduction to Psychological Research and Ethics (PSY-260), Instructional Planning and Assessments for Elementary Teacher Candidates (ELM-210), Nursing Process IV: Medical-Surgical Nursing (NUR 411), Managing Projects And Programs (BUS 5611), Introduction To Computer And Information Security (ITO 310), Nurs & Healthcare I: Foundations [Lec] (NURS356), Nutrition and Exercise Physiology (NEP 1034), Foundational Concepts & Applications (NR-500), Professional Application in Service Learning I (LDR-461), Advanced Anatomy & Physiology for Health Professions (NUR 4904), Principles Of Environmental Science (ENV 100), Operating Systems 2 (proctored course) (CS 3307), Comparative Programming Languages (CS 4402), Business Core Capstone: An Integrated Application (D083), Chapter 15 Anxiety and Obsessive-Compulsive Disorders, Database Systems Design Implementation and Management 9th Edition Coronel Solution Manual, Summary Intimate Relationships - chapters 1, 3-6, 8-11, 13, 14, Active Learning Template Nursing Skill form Therapeutic Communication, Wong s Essentials of Pediatric Nursing 11th Edition Hockenberry Rodgers Wilson Test Bank, EDUC 327 The Teacher and The School Curriculum Document, 1.1 Functions and Continuity full solutions. Collect the precipitate of benzoic acid by vacuum filtration. Essentially, we are drawing the reverse order of Fischer esterification so, in the first step the ester is protonated promoting the nucleophilic attack of water: Notice that just like the Fischer esterification, the process is an equilibrium which makes the reaction a little challenging as it may require higher temperatures and removal of the alcohol as it is formed to push the equilibrium forward. For HCrO, Ka is very large and Ka is 3.10 x 10-. B. The mechanism for the reaction is quite complex. Is the mechanism SN1 or SN2? When examining the 1H NMR spectrum no peaks were observed in the 10-13 ppm range indicating presence of benzoic acid. 0000000016 00000 n
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This step involves the intramolecular migration of hydrogen atoms. 0000009431 00000 n
- Maurice Jan 21, 2020 at 21:52 Draw the acetal produced when ethanol adds to ethanal. Selva and Tundo explored the reaction of DMC with mercaptobenzoic acids and carboxylic acids bearing OH substituents in the presence . Carbonyl is a weakly electrophilic compound that is attacked by strong nucleophiles. 0000010044 00000 n
A. Draw the organic intermediate of this reaction. Concentrated sulfuric acid is added as a catalyst in the esterification procedure, even though another acid (benzoic acid) is one of the organic reagents used. Fischer esterification of benzoic acid-1 - Fischer esterification of benzoic acid Purpose: The goal - Studocu Fischer esterification of benzoic acid lab report fischer esterification of benzoic acid purpose: the goal of this experiment is to use reaction called fischer Skip to document Ask an Expert Sign inRegister Sign inRegister Home Answer the following questions about this reaction. A large amount of acetic acid is used to increase the yield of the product by shifting equilibrium in a forward direction. Checked by C. S. Marvel and Tse-Tsing Chu. If a solution of methyl alcohol and benzoic acid containing a small amount of sulfuric acid is headed under reflux for about an hour the ester methyl benzoate is formed. 0000009002 00000 n
chloride pellets to the oil left and heat 0000010571 00000 n
Draw t. Draw the organic products for the following chemical reactions. Draw the structure of the major organic product formed in the reaction. obtained, After second time an oily mixture was <<3baea9eb20b21f4494ce8fadbea0b8fb>]>>
Using the "rule of six", predict the solubilities in water of benzoic acid, methanol, and methyl benzoate. However, it can be simplified by the overall equation: C 7 H 8 (l) +2 KMnO 4 (aq) -> KC 7 H 5 O 2 (aq) + 2 MnO 2 (s) + KOH (aq) + H 2 O (l) )%2F15%253A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives%2F15.07%253A_Preparation_of_Esters, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), source@https://2012books.lardbucket.org/books/introduction-to-chemistry-general-organic-and-biological, status page at https://status.libretexts.org. H)B;+_?btR')Cst4 E\`DL7R?Z*I]9QN++C0ssSu u$j=p}y@kQLv?mF~or9{EMQ&g7ZD]Ut
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Feb 17, 2008 1 download | skip . Figure 1: Fischer Esterification Mechanism of the Formation of Benzocaine 2. Psst: If you find my website helpful or enjoyable, please join my newsletter and/or send me an emailI want to hear from you! Organic Chemistry 1 and 2Summary SheetsAce your Exam. Predict the product of the reaction of p-methyl benzoic acid with each of the following: CH_3MgBr in ether, then H_3O^+. Fischer Esterification: Fischer esterification is a synthetic reaction used in the formation of esters from carboxylic acids and alcohols. The percent recovery of methyl benzoate for the experiment was 62.69%. Legal. Esterification of benzoic acid to give methyl benzoate - Theory: Fig 1 : Esterification mechanism of - Studocu benzoic acid to give methyl benzoate experiment esterification of benzoic acid to give methyl benzoate objectives: the objectives of this experiment is to heat Skip to document Ask an Expert Sign inRegister Sign inRegister Home The equation (4) is also wrong, with 33 H at left-hand side and 28 at right. *bV~l60mf[/;385CWd8\*l-(inVz:FRtLiVBE\?c\0CFvPeT(6".qpKi:*=J eEyn@yj),h%L;~38(=LeeT4c nr2Hi2~4K>u5[n r= 4cr0mg&XA36*jTGblW:%oe v$ wukg3pT9BH[Xh~_q9N1MI#hz11zmiI( 6TLgx;gENY^5[cU`eSM(NP},G{YI}eo;F/eSf2- ccnQ~;o{P*]3O8t0Z,jsb;L&6Kmh(u&6}X
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Zj[[|BsRk2!pl`n?P]WMFSHog7 n5+g/dU[yp[ However, the mechanism is a little different. 11. remove the unreactive benzoic acid. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. r&L6UJAMqoyp :"ek@ V$xt6,pi0x.kYl,^OX&mHtTXgf! We have seen that all the steps in the Fischer esterification are reversible and the equilibrium is shifted toward the ester product by using an excess of alcohol. 0000003466 00000 n
The acid catalyzed esterification of benzoic acid w ith methanol can be represented as in Figure 3. 0000013019 00000 n
soln into round-botttom flask, Wash drying agent with 3 to 5 ml of t- 0000005749 00000 n
Ask me anything over Zoom whenever I am online! Also, while separating the layers, there was some emulsion during mixing, so again eventual product may have been lost because the layers did not completely separate. The aim of the study was to develop a drug delivery system for specific targeting in colon cancer. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Moles of methanol= 19.8g/32.04g/mol=0 mol 772C HWKs6WH$(N=%9e%: AL3&,i_ L0Y9R`ja8lv:u;=+p`V{=/ &.K{)Uxq6{pK,>A80V{xqb$l1[y-c99tdDIJJ>y>Y E IU0'X6E7ewWwPC^n`p7COV0zXc}`)D9cCi37APNOG-H)BNbX\,$evu^h>?n5J++[WV[kO77;5)%]d ;+ copyright 2003-2023 Homework.Study.com. Draw the structures of the reactants or products of the following Fischer Esterification reactions. Draw the product you would obtain from the acid-catalyzed reaction of \beta-D-galactopyranose with ethanol. 0000009123 00000 n
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hX[o:+~G+\J)- substance or 0000007524 00000 n
krCsS ' xweUI*Y{WsT%%U#9>0>PUb5*+n" zb"e([J'}b. { Acid_Anhydrides_react_with_alcohols_to_form_esters : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.
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