Chem 31.

1 Post Lab 3
11 May 2015

Experiment 8
CARBONYL COMPOUNDS AND
CARBOHYDRATES

Aldehydes and Ketones

Synthesis of Aldehydes
1. Oxidation of 1 Alcohols

2. Ozonolysis of Alkenes

Synthesis of Ketones
1. Ozonolysis of Alkenes

2. Ketones from Nitriles

Nucleophilic Addition to the

Carbonyl Carbon
Note: aldehydes are more reactive than ketones,
product: 2 alcohol or 3 alcohol

Nucleophilic Addition to the

Carbonyl Carbon
Mechanism:

Reaction with 2,4 DNP

Solid, oily
derivative

Iodoform test: methyl ketones

Yellow precipitate

Tollens Test: test for aldehydes

Silver mirror

Carbohydrates
Polyhydroxy aldehydes or ketones
Classification:
A. Hydrolysis
1. Monosaccharides (glucose, fructose, galactose)
2. Disaccharides (sucrose, lactose, maltose)
3. Polysaccharides (starch, amylose, amylopectin)
B. Functional groups
1. Aldoses (glucose)
2. Ketoses (fructose)
C. Number of Carbon atoms
1. Hexoses (glucose)
2. Pentoses (fructose)

Glucos
e

Glucose +
fructose

fructos
e

galacto
se

Glucose + galactose
Glucose +
glucose

Carbohydrates

Structural Formulae for

Monosaccharides

Anomers
Diastereomers which differ only at the hemiacetal or
acetal carbon are called anomers. Can be an anomer or
anomer depending on the location of the OH group

Polysaccharides

Hemiacetal Carbon
The essential features of a hemiacetal carbon are an OH
and an OR group attached to the same carbon atom.

Hemiacetal Carbon

aldehyde

Hemiacetal carbon carbonyl

carbon
(marked with an asterisk)

Hemiacetal Carbon

ketone

Carbohydrates are reactive only if

it is in the open chain structure

Hydrolysis of Polysaccharides

Tollens test for Aldoses

Silver mirror

Molisch Test: a color reaction

Carbohydrates are hydrolyzed by

sulfuric acid then the monomers Positive: purple ring at the interface
of two liquids
are dehydrated to furfural

Benedicts Test: test for reducing

sugars

Of the sugar tested, only sucrose

gave a negative for benedicts
test while the hydrolysate of
sucrose is positive. Why?

Osazone Formation

Yellow crystalline solid

Useful for identifying simple

sugars (time for the crystals to
appear)
Sample
Time for osazone
formation
Fructose

2 min

Glucose

4-5 min

Lactose

Soluble in hot water

Sucrose

30 min (hydrolysis)

Epimers
Pair of diastereomers that differ only in configuration at only a
single tetrahedral chirality center.

mannose and glucose are C2 epimers

Killiani- Fischer synthesis

Ruff Degradation

Glycosidic linkages of Disaccharides

vs

Experiment 9
ACYL COMPOUNDS: SOAPS AND
DETERGENTS

Acyl Compounds: Carboxylic

Acid Derivatives

Acyl Substitution: Nucleophilic AdditionElimination at the Acyl Carbon

The result: substitution at the acyl carbon
Key mechanism: formation of a tetrahedral intermediate

Acyl Substitution: Nucleophilic AdditionElimination at the Acyl Carbon

Specific Example:

Relative Reactivity of Acyl

Compounds
Acyl chlorides are the most reactive toward nucleophilic
addition- elimination and amides are the least reactive.

General Synthesis

Acidity of Acyl Compounds

Carboxylic acids are acidic compounds that can react
with a base. (Bronsted- Lowry base)

Strong acids
Soluble in both
NaOH and NaHCO3

Weak acids
Soluble in NaOH
but not in NaHCO3

Sulfonic acids RSO3H

Carboxylic acids
RCOOH

Phenols (Ar-OH)

Hydrolysis of Acyl Compounds

Product: carboxylic acid and the leaving group w/ hydrogen

Soap Formation

Cookin
g oil
Soap is formed thru base hydrolysis of cooking
oil.
The process is called saponification

Detergent

Sulfated

Alkylated to be more
environmentally
friendly (biodegradable
and soluble)

Soap and detergents have

the same action on dirt. It
creates micelles where the
dirt (grease) is dissolved by
the non polar tail and the
polar head projects outward
to dissolve in water

Reaction with soft and hard water.

Detergents offer an advantage over soaps
because they function well in hard water.
They dont produce scum in hard water.
Calcium, iron and magnesium salts of
alkanesulfonates and alkyl hydrogen
sulfates are largely water soluble. Soaps,
by contrast, form precipitates, the ring
around the bathtub, when they are used
in hard water.

Emulsifying Action
Both are able to emulsify two insoluble liquids because
both have polar and non- polar moiety in the molecule.

Experiment 10
AMINES, AMINO ACIDS and
PROTEINS

General Structure

Amines (1, 2, 3)

Solubility of amine compounds

Amines (5<C) are soluble in water due to Hydrogen
bonding; are basic
1, 2 amines are also
capable of
intermolecular H
bonding (higher boiling
point than 3 amine)
Amino acids are zwitterion ions; it
has a basic and acid part in one
molecule

Relative basicity of amine

compounds

Alkyl substituted ammonia (amines)

are more basic than amine because
of the electron donating properties of
alkyl groups. (electron pair is more
available)

Relative basicity of aromatic amines

Aromatic amines are less basic

than alkyl amines because the
electrons are localized in the ring.

Relative basicity of substituted

aniline

Aniline with electron donating

groups increases basicity
(alkyl)
Unknown that is insoluble in water but
soluble in aqueous acid is most probably an
amine.

Amino acids and proteins

Protein structure

Alpha helix

Beta
sheets

myoglobuli

Ninhydrin Test: test for amino acid

Purple colored
complex

Biuret Test: test for proteins

Violet colored
complex

Diazonium Coupling Reaction

Diazonium salt

Diazonium salt Reaction Series

Lead Acetate test for proteins

The sulfur group of cysteine and cystine is liberated by
heating with strong alkali. If lead ions are present, lead
sulfide is formed as dark precipitate.

END OF POST LAB 3

EXAM: 18 May 2015