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Based on the results of the solubility tests and chemical tests, what is the most probable structure of C6H5C3H5O? Draw your answer in the box You may draw the compound usingline-bond formula OR Lewis structure.   Problem statement: You were tasked to propose a structure for a compound with a chemical formula of C6H5C3H5O. In the laboratory, the compound appears as a clear, colorless liquid.

Based on the results of the solubility tests and chemical tests, what is the most probable structure of C6H5C3H5O? Draw your answer in the box You may draw the compound usingline-bond formula OR Lewis structure.   Problem statement: You were tasked to propose a structure for a compound with a chemical formula of C6H5C3H5O. In the laboratory, the compound appears as a clear, colorless liquid.

EBK A SMALL SCALE APPROACH TO ORGANIC L
EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN:9781305446021
Author:Lampman
Publisher:Lampman
Chapter47: Benzocaine
Section: Chapter Questions
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Based on the results of the solubility tests and chemical tests, what is the most probable structure of C6H5C3H5O? Draw your answer in the box You may draw the compound usingline-bond formula OR Lewis structure.

 

Problem statement:
You were tasked to propose a structure for a compound with a chemical formula of C6H5C3H5O. In the laboratory, the compound appears as a clear, colorless liquid.

See table 1, for the results of solubility tests for C6H5C3H5O.

Table 1. Results of the solubility tests for C6H5C3H5O.

SOLUBILITY TEST

OBSERVATIONS

+(soluble/miscible)/

- (insoluble)

distilled water

two layers of liquid

-

10% NaHCO3

two layers of liquid

-

10% NaOH

two layers of liquid

-

10% HCl

two layers of liquid

-

concentrated H2SO4

pinkish solution

+

Based on the results of the solubility tests, the compound can be grouped in VI, which is insoluble in water, 10% NaOH and 10% HCl but soluble in concentrated H2SO4.

If the compound is water-insoluble but soluble in concentrated H2SO4, it is most probably an alcohol, aldehyde, anhydride, ester, ether, ketone, or an unsaturated hydrocarbon.

The functional group/class is identified to be Methyl Ketone, base on the results of the chemical tests on Table 2.

CHEMICAL TEST

OBSERVATIONS

+(compound tested positive for the chemical reaction)/

otherwise (-) 

Molisch test

turbid colorless solution

-

2,4-DNP test

formation of orange-yellow precipitates

+

Tollen’s test

turbid colorless solution

-

Ninhydrin test

clear pale-yellow solution

-

iodoform test

clear pale-yellow solution

+
GENERAL SCHEMATIC DIAGRAM FOR DETERMINING THE FUNCTIONAL GROUP OF AN ORGANIC COMPOUND UNENOWN COMPOUND Logend: (4)-soluble/miscible or positive test i-)- insolubleimmiscible or negative test WATER SOLUBILITY TEST INSOLUBLE SOLUBLE Solubility in 10% NAHCO Litmus paper test ((+) neutral acidic basic Solubility in 10% NaOH CARBOXYLIC ACID Ninhydrin test Ninhydrin test Molisch test Fed, test (+) CARBOXYLIC Biuret test Hard water test Biuret test Benedict's test ACID (+) (-) (+) (-) PHENOL Solubility in 10% HCI | PROTEIN PROTEIN I | AMINO ACID | REDUCING SUGAR AMINO ACID NON-REDUCING DETERGENT SOAP SUGAR ( (+) Lead acetate test Lead acetate test Ninhydrin test Solubility in concentrated H,S0 (-) (+) ( (+) AMINE NON-SULFUR- CONTAINING SULFUR- CONTAINING AMINO ACID NON-SULFUR- CONTAINING SULFUR- CONTAINING AMINO ACID 2,4-DNP Test Biuret Test AMINO ACID AMINO ACID Bra with light (+)(-) Molisch Test (-) (+) Tollen's Test AMINO ACID PROTEIN hot acidic KMno test ALKANE, ALKYLBENZENE POLYSACCHARIDE 24DNP Test BENZENE (-) (+) (+) ) (AROMATIC HYDROCARBON) Lead acetate tes TERTIARY ALCOHOL (+) (-) (+) PRIMARY and SECONDARY ALCOHOL KETONE ALDEHYDE Tollen's Test NON-SULFUR- CONTAINING SULFUR- CONTAINING AMINO ACID Bayar'stest ledofarm Test AMINO ACID (+) (+) (-) hot acidic KMnOc test KETONE ALDEHYDE METHYL KETONE NON-METHYL KETONE (+) (-) ALKYNE ALKENE lodaform Test PRIMARY and SECONDARY ALCOHOL TERTIARY ALCOHOL Reaction with (+) (-) Ammoniacal AgNOz (+) (-) METHYL NON-METHYL KETONE КЕTONE TERMINAL ALKYNE INTERNAL ALKYNE
Transcribed Image Text:GENERAL SCHEMATIC DIAGRAM FOR DETERMINING THE FUNCTIONAL GROUP OF AN ORGANIC COMPOUND UNENOWN COMPOUND Logend: (4)-soluble/miscible or positive test i-)- insolubleimmiscible or negative test WATER SOLUBILITY TEST INSOLUBLE SOLUBLE Solubility in 10% NAHCO Litmus paper test ((+) neutral acidic basic Solubility in 10% NaOH CARBOXYLIC ACID Ninhydrin test Ninhydrin test Molisch test Fed, test (+) CARBOXYLIC Biuret test Hard water test Biuret test Benedict's test ACID (+) (-) (+) (-) PHENOL Solubility in 10% HCI | PROTEIN PROTEIN I | AMINO ACID | REDUCING SUGAR AMINO ACID NON-REDUCING DETERGENT SOAP SUGAR ( (+) Lead acetate test Lead acetate test Ninhydrin test Solubility in concentrated H,S0 (-) (+) ( (+) AMINE NON-SULFUR- CONTAINING SULFUR- CONTAINING AMINO ACID NON-SULFUR- CONTAINING SULFUR- CONTAINING AMINO ACID 2,4-DNP Test Biuret Test AMINO ACID AMINO ACID Bra with light (+)(-) Molisch Test (-) (+) Tollen's Test AMINO ACID PROTEIN hot acidic KMno test ALKANE, ALKYLBENZENE POLYSACCHARIDE 24DNP Test BENZENE (-) (+) (+) ) (AROMATIC HYDROCARBON) Lead acetate tes TERTIARY ALCOHOL (+) (-) (+) PRIMARY and SECONDARY ALCOHOL KETONE ALDEHYDE Tollen's Test NON-SULFUR- CONTAINING SULFUR- CONTAINING AMINO ACID Bayar'stest ledofarm Test AMINO ACID (+) (+) (-) hot acidic KMnOc test KETONE ALDEHYDE METHYL KETONE NON-METHYL KETONE (+) (-) ALKYNE ALKENE lodaform Test PRIMARY and SECONDARY ALCOHOL TERTIARY ALCOHOL Reaction with (+) (-) Ammoniacal AgNOz (+) (-) METHYL NON-METHYL KETONE КЕTONE TERMINAL ALKYNE INTERNAL ALKYNE
+ Table 3. Solubility groups to dassify an organic compound based on solubility. DESCRIPTION SOLUBILITY GROUP Compounds with 5 carbons or less and containing either oxvgen, nitrogen, or sulfur. Increasing the carbon chain to six or more decreases solubility in water. Branching increases solubility in water. I If the aqueous solution is neutral, the compound is most probably a low- Soluble in both water and molecular-weight alcohols, aldehyde, or ketone. ether If the aqueous solution is acidic, the compound is most probably a low- molecular-weight carboxylic acid or a sulfonicacid. If the aqueous solution is basic, the compound is most probably a low- molecular-weight amine. If the aqueous solution is acidic, the compound is most probably a polycarboxylic acid or an amine salt. II Soluble in water but not in If the aqueous solution is neutral, the compound is most probably a metal or ammonium salt of a carboxylic acid, carbohydrate, amino acid, or polyhydric alcohol. ether III If the compound is water-insoluble but soluble in dilute bases, it is most probably a sulfonic acid, carboxylic acid, or a phenol with electron- Insoluble in water but soluble in 10% NaOH and withdrawing substituents. 10% NaHCO, IV If the compound is water-insoluble but soluble in dilute strong bases, it is Insoluble in water and 10% NaHCO, but soluble most probably a phenol, enol, or a 1,3-dicarbonyl compound. in 10% NaOH V Insoluble in water and 10% NaOH but soluble in 10% HCl If the compound is water-insoluble but soluble in dilute acids, it is most probably an amine. VI Insoluble in water, 10% If the compound is water-insoluble but soluble in concentrated H.so, it N2OH and 10% HCI but soluble in concentrated is most probably an alcohol, aldehyde, anhydride, ester, ether, ketone, or an unsaturated hydrocarbon. H:SO. VII Insoluble in water, 10% NaOH, 10% HCl and concentrated H;SO, If the compound is insoluble in water or in any aqueous solution, it is most probably an alkyl or aryi halide, aromatic hydrocarbon, alkane, or a diaryl ether.
Transcribed Image Text:+ Table 3. Solubility groups to dassify an organic compound based on solubility. DESCRIPTION SOLUBILITY GROUP Compounds with 5 carbons or less and containing either oxvgen, nitrogen, or sulfur. Increasing the carbon chain to six or more decreases solubility in water. Branching increases solubility in water. I If the aqueous solution is neutral, the compound is most probably a low- Soluble in both water and molecular-weight alcohols, aldehyde, or ketone. ether If the aqueous solution is acidic, the compound is most probably a low- molecular-weight carboxylic acid or a sulfonicacid. If the aqueous solution is basic, the compound is most probably a low- molecular-weight amine. If the aqueous solution is acidic, the compound is most probably a polycarboxylic acid or an amine salt. II Soluble in water but not in If the aqueous solution is neutral, the compound is most probably a metal or ammonium salt of a carboxylic acid, carbohydrate, amino acid, or polyhydric alcohol. ether III If the compound is water-insoluble but soluble in dilute bases, it is most probably a sulfonic acid, carboxylic acid, or a phenol with electron- Insoluble in water but soluble in 10% NaOH and withdrawing substituents. 10% NaHCO, IV If the compound is water-insoluble but soluble in dilute strong bases, it is Insoluble in water and 10% NaHCO, but soluble most probably a phenol, enol, or a 1,3-dicarbonyl compound. in 10% NaOH V Insoluble in water and 10% NaOH but soluble in 10% HCl If the compound is water-insoluble but soluble in dilute acids, it is most probably an amine. VI Insoluble in water, 10% If the compound is water-insoluble but soluble in concentrated H.so, it N2OH and 10% HCI but soluble in concentrated is most probably an alcohol, aldehyde, anhydride, ester, ether, ketone, or an unsaturated hydrocarbon. H:SO. VII Insoluble in water, 10% NaOH, 10% HCl and concentrated H;SO, If the compound is insoluble in water or in any aqueous solution, it is most probably an alkyl or aryi halide, aromatic hydrocarbon, alkane, or a diaryl ether.
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