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

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

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

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.31P: Show reagents and experimental conditions to synthesize the following compounds from 1-propanol (any...

See similar textbooks

Similar questions

Propose 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.
Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.
The fungus responsible for Dutch elm disease is spread by European bark beetles when they burrow into the tree. Other beetles congregate at the site, attracted by the scent of a mixture of chemicals, some emitted by other beetles and some coming from the tree. One of the compounds given off by female bark beetles is 4-methyl-3-heptanol. Suggest an efficient synthesis of this pheromone from alcohols of five carbon atoms or fewer.
Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)
Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.
The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.
1-Phenyl-2-butanol is used in perfumery. Show how to synthesize this alcohol from bromobenzene, 1-butene, and any necessary inorganic reagents.
Using your reaction roadmaps as a guide, show how to convert 4-methyl-1-pentene and carbon dioxide into 5-methylhexanoic acid. You must use 4-methyl-1-pentene and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.
Account for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.
List the products of the reaction of acetaldehyde and acetone with sodium ethoxide in ethanol.Explain it briefly
Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.
The odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate) (a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender (b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester. (c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).