1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl ether (ethyl isobutyl ether). Be sure that at some point in one or more of your syntheses you utilize the following reagents (not all in the same synthesis, however): PBR3, SOCI2, p- toluenesulfonyl chloride (tosyl chloride), NaH, ethanol, 2-methyl-1-propanol (isobutyl alcohol), concentrated H2SO4, Hg(OAc)2, ethene (ethylene). (b) Evaluate the relative merits of your syntheses on the basis of selectivity and efficiency. (Decide which ones could be argued to be the "best" syntheses and which might be "poorer" syntheses.)

1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl ether (ethyl isobutyl ether). Be sure that at some point in one or more of your syntheses you utilize the following reagents (not all in the same synthesis, however): PBR3, SOCI2, p- toluenesulfonyl chloride (tosyl chloride), NaH, ethanol, 2-methyl-1-propanol (isobutyl alcohol), concentrated H2SO4, Hg(OAc)2, ethene (ethylene). (b) Evaluate the relative merits of your syntheses on the basis of selectivity and efficiency. (Decide which ones could be argued to be the "best" syntheses and which might be "poorer" syntheses.)

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.38P: Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline...

See similar textbooks

Similar questions

Using benzene and any necessary organic or inorganic reagents, suggest efficient syntheses of (a) Isobutylbenzene, C6H5CH2CH(CH3)2 (b) (2,2-Dimethylpropyl)benzene, C6H5CH2C(CH3)3
starting with 1-bromobutane give a sequence of laboratory reactions which could be used to produce 1-phenyl-1-pentanol
Draw a flowchart showcasing the purification step done for the reaction under basic conditions (the basic reaction of 4-methoxyacetophenone with bleach, sodium hydroxide, and acetone), starting from the crude reaction mixture all the way to the isolated solid product. Assume for this drawing that the reaction was complete, and that none of the intermediates are found in the crude mixture. There may still be however traces of your starting material in the crude mixture, along with any excess reagents
You are given a mixture of benzoic acid, 2-naphthol and 1,4-dimethoxybenzene and you are asked to separate the mixture into its following compounds. You are limited to using dichloromethane, pentane, cyclohexane and ethyl acetate as organic solvents. This doesn't involve solvents used to convert the 3 compounds to ionic salts. Suggest possible organic solvents and explain a procedure you would carry out to separate the 3 mixtures briefly.
Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH3)3 as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanoleliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.
(i) Name, draw and describe the organic product of the reaction between 2-methylbut-1-ene and H2O in the presence of H2SO4 and provide a clear rationale as to why this is the major product of the reaction. (ii) The elimination reaction between 2-bromobutane and NaOCH2CH3 gives two organic products. Draw a mechanism for the reaction which produces the major organic elimination product and provide a rationale as to why that is the major product.
Suggest a synthesis for the molecule below starting from benzene, alcohols of four carbons or fewer and any inorganic reagents
Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline hydrogen peroxide gives the following alcohol. Of the four possible cis,trans isomers, one is formed in over 85% yield. (a) Draw structural formulas for the four possible cis,trans isomers of the bicyclic alcohol. (b) Which is the structure of the isomer formed in 85% yield? How do you account for its formation? Create a model to help you make this prediction.
In two parts, outline the Electrophilic aromatic substitution for the nitration of benzene using nitric acid and sulfuric acid: A) In part I, using the curved arrow formalism, outline a mechanism for the formation of the nitronium ion, NO2+ starting from nitric acid, HNO3 and sulfuric acid, H2SO4. Do not forget to show all of the formal charges for each atom that is not zero in this mechanism. B) Starting from the nitronium ion that you generated in part “a” from above, outline the Electrophilic Aromatic Substitution of this ion with benzene.
Give an explanation, why the acidity of these phenolic derivatives give these pKa value? Describe it by using the electronic effect on the acidity.
3. Obtain acetophenone and acetaldehyde by reaction of glycols with periodic acid. Justify your answer with the reaction mechanism.
Starting with benzene, give a sequence of laboratory reactions which could be used to prepare p-isopropylaniline. If separation of ortho, meta, or para-isomers is required, give evidence that it is feasible.