Identify each compound below as either a protic solvent or an aprotic solvent. H3C CH3 N N. H3C H,C CH3 `CH3 H3C-C=N N H3C-OH HO НО H Ethane-1,2-diol (Ethylene glycol) Methanamide Ethanenitrile Methanol Hexamethylphosphorotriamide (ΗMPA) (Formamide) (Acetonitrile) O=0
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In which solvents in Problem 2.55 do you think NaCl will have a substantially greater solubility than in dimethyl sulfoxide
(DMSO)? Explain.
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- How to set-up a separatory funnel? Please narrate the process in 5 sentences.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?4-bromobenzoic acid (1.0 g) is dissolved in 20 ml dichloromethane. After addition to a separatory funnel, the dichloromethane solution is treated with 20 ml 3.0 M NaOH solution. After the layers are separated, which layer(s) will contain an organic compound (non-solvent)? What would happen if the aqueous layer is treated with 20 ml 3.0 M HCl?
- Q1. Discuss the role of the following reagents in the extraction of caffeine. a. Vinegarb. Baking soda Q2. What are emulsions? Why do they form during extractions? How is their formation minimized? Q3. Why is it necessary to turn the separatory funnel upside down and to open thestopcock?A chemist was charged with the task of making amino alcohol 2. This chemist decided to attempt a Grignard reaction between two equivalents of phenylmagnesium bromide and amino ester 1. To this end, two equivalents of the Grignard reagent were added to a flask containing a stirred THF solution of ester 1 at -78 °C. Upon acidic aqueous work-up of the reaction mixture, the desired alcohol 2 was not isolated, even though one equivalent of methanol was produced and all the starting materials were consumed. Instead, two products with the molecular formulae of C6H6 and C7H13NO were obtained in a 2:1 ratio, respectively. Identify the structures of these two products and describe, mechanistically, how they were formed.You have learned that ester may be hydrolyzed in aqueous base. Why does a workup using 50ml of 10% NaOH and 50g of ice not hydrolyze a nitro benzocaine derivative?
- Treatment of pentanedioic (glutaric) anhydride with ammonia at elevated temperature leads to a compound of molecular formula C5H7NO2. What is the structure of this product? [Hint: You need to think about the reactivity not only of acid anhydrides but also of amides and carboxylic acids]Which layer (aqueous or organic) would you expect to find 3,5-dimethylaniline in the following liquid-liquid extractions? Explain. Draw chemical structures to help explain your answers. If the structure of themolecule changes in the aqueous solution, then draw the new structure. i. water and dichloromethaneii. aq. NaOH and dichloromethaneiii. aq. HCl and dichloromethane(a) Write the structures of main products when aniline reacts with the following reagents :(i) Br2 water (ii) HCI (iii) (CH3CO)2O/pyridine(b) Arrange the following in the increasing order of their boiling point :C2H5NH2, C2H5OH, (CH3)3N(c) Give a simple chemical test to distinguish between the following pair of compounds : (CH3)2NH and (CH3)3N
- For the following pairs, determine what could be the best solvent to differentiate them based on their predicted solubility. 1. beta-naphthol and butyric acid 2. anthracene and benzylamine 3. p-xylene and benzaldehydeo - Nitroaniline is more soluble in ethanol than p - nitroaniline. Propose a scheme by which a pure sample of o-nitroaniline might be obtained from this reactionPropose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitroaniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.