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Organic Chemistry Lab > Exercise 10: ALDEHYDES AND KETONES > Flashcards

Exercise 10: ALDEHYDES AND KETONES Flashcards

1
Q

organic compounds both containing a carbonyl functional group
(C=O)

 has two more bonds that may be occupied by hydrogen or alkyl or
aryl substituents

A

ALDEHYDES AND KETONES

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2
Q

if one R is hydrogen =
If both R are neither H =

A

aldehyde

ketone

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3
Q

naturally occurring
organic
compounds, often
combined with
other functional
groups

 can be found in
plants, animals,
and even
microorganisms

A

ALDEHYDES AND KETONES

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4
Q

(cinnamon bark)

A

cinnamaldehyde

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5
Q

(musk deer)

A

muscone

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6
Q

(vanilla bean)

A

vanillin

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7
Q

(male sex hormone)

A

testosterone

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8
Q

(lemongrass)

A

citral

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9
Q

(female sex hormone)

A

progesterone

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10
Q

(a fungal toxin)

A

helminthosporal

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11
Q

(spearmint & caraway

A

carvone

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12
Q

(adrenal hormone)

A

cortisone

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13
Q

camphor tree)

A

camphor

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14
Q

largely responsible some of the shared physicochemical
properties of aldehydes and ketones

a - group because of the greater
electronegativity of the oxygen

as a result of this polarization, the carbonyl group is
susceptible to

A

CARBONYL GROUP

highly polarized

nucleophilic attack

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15
Q

commonly
synthesized in the
laboratory through

of alcohols

A

oxidation reaction

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16
Q

are oxidized to
aldehydes while

are oxidized to ketones

A

primary alcohols

secondary alcohols

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17
Q

TEST FOR CARBONYL GROUP

A

• 2,4-DNPH TEST
• SODIUM BISULFITE TEST

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18
Q

2,4-DNPH (BRADY’S) TEST results

acetone

A

clear orange solution

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19
Q

2,4-DNPH (BRADY’S) TEST results

acetophenone

A

yellow-orange precipitate

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20
Q

2,4-DNPH (BRADY’S) TEST results

acetone

A

Clear orange soln

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21
Q

2,4-DNPH (BRADY’S) TEST results

formaldehyde

A

reddish orange precipitate

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22
Q

detect the presence of carbonyl
group

A

2,4-DNPH (BRADY’S) TEST

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23
Q

 reagent: Brady’s reagent

named after Oscar Brady

A

(2,4-
dinitrophenylhydrazine in methanol);

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24
Q

positive result: 2,4-DNPH (BRADY’S) TEST

A

yellow to orange precipitate for
aldehydes

red to orange precipitate for
ketones

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25
Q

condensation reaction; aldehyde
reacts with 2,4-DNPH to forms an while ketone reacts with
to form a

A

aldehyde 2,4-
dinitrophenylhydrazone

ketone 2,4-dinitrophenylhydrazone

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26
Q

SODIUM BISULFITE TEST results

acetaldehyde

A

white precipitate

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27
Q

SODIUM BISULFITE TEST results

acetone

A

white precipitate

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28
Q

used to determine if a compound is an aldehyde or
an aliphatic methyl ketone

A

SODIUM BISULFITE TEST

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29
Q

 reagent: sodium bisulfite

A

SODIUM BISULFITE TEST

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30
Q

SODIUM BISULFITE TEST
 positive result:

A

white precipitate

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31
Q

the reacts with
sodium bisulfite by breaking the pi bond of the carbonyl
group through - attack; the - then
attaches to the original carbonyl group to form the bisulfite
addition compound

A

aldehyde or the methyl ketone

nucleophilic

bisulfite ion

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32
Q

with ketones, only will yield positive result
(ketones with - groups sterically hinders the bisulfite ion
in attaching to the carbonyl group)

A

methyl ketones, bulky

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33
Q

SCHIFF’S TEST resuts

acetophenone

A

Clear colorless soln

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34
Q

SCHIFF’S TEST resuts

acetone

A

clear colorless solution

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35
Q

SCHIFF’S TEST resuts

acetophenone

A

clear colorless solution

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36
Q

SCHIFF’S TEST resuts

benzaldehyde

A

magenta red solution

37
Q

SCHIFF’S TEST resuts

formaldehyde

A

magenta red solution

38
Q

used to differentiate aldehydes from ketones

A

SCHIFF’S TEST

39
Q

 reagent: Schiff’s reagent (); named after Hugo Schiff

A

sodium bisulfite with the organic dye
pararosaniline hydrochloride

40
Q

SCHIFF’S TEST
 positive result:

A

magenta red solution

41
Q

oxidation of aldehyde to carboxylic acid;
reaction involved is the same as explained in the
sodium bisulfite test

 some ketones may also produce a color change but
not a magenta red color

A

SCHIFF’S TEST

42
Q

TOLLENS’ TEST results

acetone

A

clear colorless solution

43
Q

TOLLENS’ TEST results

5% glucose

A

silver mirror precipitate

44
Q

TOLLENS’ TEST results

benzaldehyde

A

turbid gray solution

45
Q

TOLLENS’ TEST results

formaldehyde

A

silver mirror precipitate

46
Q

used to differentiate aldehydes from ketones

A

TOLLENS’ TEST

47
Q

 reagent: Tollens’ reagent (to render solution colorless);

named after Bernhard
Tollens

A

silver nitrate with sodium hydroxide and excess
ammonium hydroxide

48
Q

TOLLENS’ TEST
 positive result:

A

silver mirror precipitate

49
Q

oxidation of aldehyde to
carboxylic acid; the - is reduced to silver while producing
the carboxylic acid-ammonium salt
product

 can detect both aliphatic and
aromatic aldehydes

A

ammoniacal silver
nitrate

Tollens’ test

50
Q

FEHLING’S TEST

acetone

A

clear blue solution

51
Q

FEHLING’S TEST

5% glucose

A

brick red precipitate

52
Q

FEHLING’S TEST

benzaldehyde

A

clear blue solution

53
Q

FEHLING’S TEST

formaldehyde

A

brick red precipitate

54
Q

used to differentiate aldehydes from ketones

A

Schiff’s Test
Fehling’s Test

55
Q

 reagent: Fehling’s reagent
(a solution of Fehling’s A prepared by mixing

and Fehling’s B prepared by mixing

named after Hermann von Fehling

A

concentrated sulfuric acid with aqueous solution of copper sulfate pentahydrate

sodium hydroxide with potassium tartrate);

56
Q

FEHLING’S TEST
 positive result:

A

brick red precipitate

57
Q

oxidation of aldehyde to
carboxylic acid; aldehyde reduces the
cupric ions in complex with- to
cuprous ions; forming cuprous oxide

Fehling’s test is very specific to produce
the positive result with an- ; - and
- give a negative result with this test

A

tartrate ions

aliphatic aldehyde

aromatic aldehydes, ketones

58
Q

TEST FOR METHYL KETONES

A

• SODIUM NITROPRUSSIDE TEST
• IODOFORM TEST

59
Q

SODIUM NITROPRUSSIDE TEST results

acetone

A

wine red solution

60
Q

SODIUM NITROPRUSSIDE TEST results

ethyl methyl ketone

A

wine red solution

61
Q

function of test: identify the presence of an acetyl group (CH3C=O)

A

SODIUM NITROPRUSSIDE TEST

62
Q

 reagent: sodium nitroprusside

A

SODIUM NITROPRUSSIDE TEST

63
Q

SODIUM NITROPRUSSIDE TEST
 positive result:

A

wine red solution

64
Q

in presence of alkali, a methyl ketone such as
acetone is converted to - ion which reacts
with nitroprusside ion [Fe(CN)5NO]2- to give

A

CH3C=OCH2- ,

highly
colored ion [Fe(CN)5NOCH2C=OCH3]2-

65
Q

is also used in clinical tests to
detect the presence of acetone in urine

A

sodium nitroprusside test

66
Q

IODOFORM TEST results

acetone

A

canary yellow precipitate

67
Q

IODOFORM TEST results

ethyl methyl ketone

A

canary yellow precipitate

68
Q

IODOFORM TEST results

ethyl acetate

A

clear colorless solution

69
Q

used to identify methyl ketones or secondary
alcohols adjacent to a methyl group

A

Iodoform test

70
Q

 reagent: Wagner’s reagent ()

A

iodine in potassium iodide in sodium
hydroxide

71
Q

IODOFORM TEST
 positive result:

A

canary yellow precipitate

72
Q

solution of I2 in KI in sodium
hydroxide reacts only for compounds
with the structure - to form iodoform

A

RCH(OH)CH3 or
RC=OCH3

73
Q

this test is very specific test and it does
not work for all ketones and does not
work also for water-insoluble
compounds

A

IODOFORM TEST

74
Q

TEST FOR SACCHARIDES

A

• MOLISCH’S TEST
• BIAL’S TEST

75
Q

MOLISCH’S TEST

5% glucose

A

purple ring at junction of two layers

76
Q

MOLISCH’S TEST

5% starch

A

purple ring at junction of two layers

77
Q

MOLISCH’S TEST

benzaldehyde

A

dark red solution

78
Q

general test for saccharides

A

MOLISCH’S TEST

79
Q

 reagent: Molisch’s reagent (

named after Hans Molisch

A

10% α-naphthol in 95% ethanol);

80
Q

MOLISCH’S TEST
 positive result:

A

purple ring at junction of two
layers

81
Q

Molisch reagent dehydrates
pentoses to - and
hexoses to -; furfural compounds further
react with- producing a purple-
colored product

A

furfural derivatives

5-hydroxymethyl furfural
derivatives

α-naphthol

82
Q

 yield rapid results while
react slower

A

monosaccharides

disaccharides

83
Q

BIAL’S TEST results

5% ribose

A

dark blue solution

84
Q

BIAL’S TEST results

5% glucose

A

clear golden brown solution

85
Q

specific test for pentoses (or carbohydrates with
five carbon chain)

A

BIAL’S TEST

86
Q

 reagent: Bial’s reagent (; named after Manfred Bial

A

orcinol, hydrochloric acid and ferric
chloride)

87
Q

BIAL’S TEST
 positive result:

A

blue solution

88
Q

Bial’s reagent dehydrates
pentoses to form -; the furfural further
reacts with - and the -
present in Bial’s reagent producing a blue
product

A

furfural

orcinol, ferric ion

Organic Chemistry Lab (5 decks)

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