Chemistry Tests of Aldehydes and Ketones Key Worksheet

Homework 7 (Chapter 19)Name _____________________________
1. Provide the IUPAC name for each of the compounds.
(a)
O
H2
C
(b)
C
C
H2
H3C
O
____________________________________________________
O
O
(c)
______________________________________
OH
O
O
_______________________________________________
(d)
O
O
(e)
O
N
H
(f)
O
O
_____________________________________________
O
(g)
O
N
Br
_____________________________________________________
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2. Provide the structure for the following compounds.
(a) p-nitrobenzamide
(b) diethyl ethanedioate
(c) ethanoic propanoic anhydride
(d) ethyl trans-pent-2-enoate
3. Draw the product for the following reactions.
(a)
O
H2O, NaOH
NH2
heat
(b)
NH2
O
O
+
O
O
(c)
(d)
O
O
H2O, H+
O
H2O, NaOH
O
2
Experiment Activity 3 Tests of Aldehydes and Ketones Key
Aldehydes and ketones both contain the carbonyl group, C=O. Their functional groups have very
similar structure. In this experiment, we are going to learn more about aldehydes and ketones by
looking at their reactions and perform tests on a variety of aldehydes and ketones to distinguish
between them.
Watch this video https://youtu.be/idzztTrFsE4 up to 11:45 minutes only (skip aldol
condensation reaction) and answer the following questions.
1. Tollen’s silver mirror test is used to distinguish between aldehydes and ketones. In the
experiment, five compounds were tested with the Tollen’s reagent. Name and draw the five
compounds.
2. In the Tollen’s silver mirror test, a decanting technique was used. What is decanting?
3. Which of the five compounds produced a positive Tollen’s silver mirror test (formation of a
silver mirror)?
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4. Which of the five compounds should porduce a positive Tollen’s silver mirror test but the
reaction was too slow to be observed?
5. Which of the five compounds produced a negative Tollen’s silver mirror test?
6. What can you conclude from the result of the Tollen’s sliver mirror test? Provide an
explanation.
7. In the addition reaction of aldehydes and ketones, sodium bisulfite was used to detect the
presence of aldehydes and ketones. Describe what happened when sodium bisulfite was
added to acetone in the addition reaction?
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The reactions of the enolate anions are also known as the haloform reactions. This is a test for
methyl ketones with an example structure that is shown below:
O
CH3
a methyl ketone
A ketone with a methyl group next to the carbonyl group will show a positive haloform test
(yellow precipitate) while aldehydes and non-methyl ketones will not have a reaction in the
haloform test.
8. In the table below, fill in the name of the five compounds that were being tested, their
structures and their haloform test results.
Compound
Structure
Results of the haloform test
9. Are the results in the haloform test as expected? Explain.
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Homework 6 (Chapter 16 and Chapter 18)
Name _____________________________
1. Provide the IUPAC name for each of the compounds.
(a)
OH
O
(b)
__________________________________________________________
COOH
OH
________________________________________________________
(c) CCl3COOH ______________________________________________________________
(d)
O2N
COOH
NO2
__________________________________________________________
(e)
HOOC
COOH
____________________________________________________
(f)
OH
H
O
NH2
O
(g)
_________________________________________________________
N
_____________________________________________________________
(h)
NH2
OH
__________________________________________________________
1
(i)
NH2
Cl
_________________________________________________________________
(j)
NH2
___________________________________________________________
(k)
N
________________________________________________________
(l)
HN
___________________________________________________________
2. Provide the structure for each of the following.
(a) tert-butylamine
(b) 2,4-dimethylaniline
(c) 4-phenylbutanoic acid
(d) 3-aminobutanoic acid
3. Classify each amino group as primary, secondary or tertiary and as aliphatic or aromatic.
(a)
NH2
HO
N
2
(b)
N
HN
4. Explain why 1-butanamine (bp 78℃) has a lower boiling point than 1-butanol (bp 117℃).
5. Hexanoic acid, heptanal and 1-heptanol have approximately the same molecular weight.
Arrange them in the order of increasing boiling point?
_____________________ < _____________________ < _______________________ (lowest bp) (highest bp) 6. Arrange these compounds in the order of increasing solubility in water: acetic acid, pentanoic acid and decanoic acid. _____________________ < ______________________ < ________________________ (least soluble) (most soluble) 7. True or False. (a) Carboxylic acids are stronger acids than alcohols but weaker acids than phenols. _____ (b) water-insoluble amines react with strong aqueous acids such as HCl to form water-solule salts. _____ (c) Aliphatic amines are stronger bases than aromatic amines. ______ 3 8. Rank the following four compounds in the order of increasing acidity. O O OH Cl OH B OH OH Cl A O O Cl C D _______ < _______ < _______ < _______ (least acidic) (most acidic) 9. Draw the form of the carboxylic acid or amine in the given pH of the solution. Compound pH 2 pH 7.4 pH 12 Acetic acid (pKa = 4.5) Ethylamine (pKa = 10.8) Benzoic acid (pKa = 4.2) Aniline (pKa = 4.6) 4