CHEM 40

Second Long Quiz

1st semester AY 2013-2014
I.

Modified True or False (28 points)

On the blank space provided, write TRUE if the statement is true otherwise CHANGE THE
UNDERLINED WORD/S to make the statement true.
1. Based on the hydrolysis test, the -glycosidic bond in starch is more susceptible to acid
cleavage than the -glycosidic linkage in the cellulose molecule.
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2. A carboxylic acid can be converted to its functional derivative by nucleophilic aromatic
substitution.
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3. Acid halides are converted to alkyl halides upon hydrolysis in water.
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4. Propanoic anhydride gives a neutral solution with water.
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5. Formation of gray precipitate is an indication of the oxidation-reduction reaction between
the ammoniacal AgNO3 and acetylene gas.
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6. Hydrocarbons are soluble in dichoromethane and insoluble in water.
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7. The Lucas and Baeyers test can classify alcohols as primary, secondary or tertiary.
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8. Esters are generally characterized by their solubility in concentrated H2SO4 solution and
unreactivity with common chemical tests.
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9. Methyl ketones and secondary alcohols with a methyl substituent attached to the carbon
bearing the OH group are oxidized by I2/KI in basic solution.
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10. All disaccharides react with Benedicts reagent producing a brick red precipitate.
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11. Diazonium salts are stable at high temperature.
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12. In proteins, glycosidic bonds link individual units of amino acids.
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13. Acetic anhydride undergoes nucleophilic acyl substitution with salicylic acid to produce
acetylsalicylic acid.

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14. Acetylene gas is prepared by reacting calcium chloride with water.
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15. Primary alcohols are more reactive towards Lucas than secondary alcohols.
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16. The higher the degree of branching in alcohol, the more soluble it is in water.
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17. Molisch test is used to identify carbohydrates based on the time of reaction with
phenylhydrazine.
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18. Upon reaction with an acid, soap produces alkylsulfonic acid, which is soluble in water.
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19. Water-insoluble amines can be made soluble by dissolving them in an aqueous base.
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20. Positive result in lead acetate test is indicated by the formation of yellow precipitate.
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21. A replacement reaction in a diazonium salt is indicated by the bubbling of the reaction
mixture.
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22. In the synthesis of aspirin, cold water is added to destroy any excess salicylic acid.
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23. Aspirin gives a positive result upon reaction with ferric chloride.
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24. Azo compounds are formed from the reaction of primary aromatic amines with nitrous acid.
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25. Ninhydrin test detects the presence of -amino group in amino acids and proteins.
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26. Among cysteine, glutamic acid, albumin, and N,N-dimethylaniline, only N,N-dimethylaniline
will give positive result for Biuret test.
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27. Terminal alkenes are reactive towards alcoholic AgNO3.
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28. All aldehydes and ketones form yellow to orange precipitate with 2,4dinitrophenylhydrazine.
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II.

STRUCTURE ELUCIDATION (17 points)

Ginger is an organic chemistry student investigating SPICEH, the substance that gives her
spicy namesake a hot taste. She was able to isolate and purify the substance with a
chemical formula C11H14O3.
1.

Compute for the degree of unsaturation,, SPICEH.

= (2+ 2C+ N-H-X)/2

2. Ginger performed the following solubilty and chemical tests below. Help her identify the
functional groups that may be present or absent in SPICEH by completing the table below.
Solubility/Chemical
Test
Solubility in water
Solubility in NaHCO3
Solubility in NaOH
Ferric chloride test
Solubility in H2SO4
Molisch test
Reaction with 2,4-DNP
Iodoform test
Baeyers test
HCl/ZnCl2

Result

Inference

+
+
+

+
+

3. Propose a possible structure of SPICEH consistent with the chemical data.

III.

IDENTIFICATION OF ORGANIC COMPOUNDS (30 points)

Given below is a schematic diagram on the identification of organic compounds. Fill up each
box with the set of letter corresponding to the identity of these compounds.
CODE

COMPOUND

CODE

ICE

NAG

PRY

QUA

SLY

Albumin

RAM

SUE

WRY

RYE

YAW

DUB

SEC

Fructose

NAB

ZEN

COMPOUND

IV.

CHEMICAL CHARACTERIZATION (25 points)

Complete the table below. Solubility and Litmus tests will NOT be considered as classification tests.

Sucrose

Lactose

Soap
Albumin

Detergent
Cellulose

Reagent
or Test

Compound
that will
give the (+)
result

Visible
Sign