23.1 Introduction To Functional Groups

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Chapter 23.

1 Functional Groups

23.1 Introduction to Functional Groups (Aprenderse Table 23.1 pg. 726)

Most organic chemistry involves substituents.

Substituents: groups attached to hydrocarbon chains.


The substituents of organic molecules often contain oxygen, nitrogen, sulfur and or
phosphorus.
They are called functional groups because there are the chemically functional parts
of the molecules.
Functional group: specific arrangement of atoms in an organic compound that is
capable of characteristic chemical reactions.
Most organic chemistry is functional-group chemistry.
Organic compounds can be classified according by their functional groups.
The symbol ‘R’ represents any carbon chains or rings attached to the functional
group.
Halocarbons: class of organic compounds containing covalently bonded fluorine
(F), Chlorine (Cl), Bromine (Br) or iodine (I). A halocarbon is a carbon-containing
compound with a halogen substituent.
Alkyl halides: Halocarbons in which a halogen is attached to a carbon of an
aliphatic chain.
Aryl Halides: Halocarbons in which a halogen is attached to a carbon of an arene
ring.
Attractions between halocarbon molecules are primarily the result of a weak van
der Waals interactions called dispersion forces.
Organic reactions procced more slowly than inorganic reactions. Catalysts are
needed for this to happen. The product most be separated by: distillation,
crystallization, or other means.
A common type of organic reaction is a substitution reaction that are the ones in
which an atom, or group of atoms, replaces another atom or group of atoms.
A halogen can replace a hydrogen atom on an alkane to produce a halocarbon.

23.2 Alcohols and Ethers

An alcohol is an organic compound with an –OH group. The –OH functional group
in alcohols is called hydroxyl group or hydroxyl function.
Aliphatic alcohols can be classified into structural categories according to the
number of R groups attached to the carbon with the hydroxyl group.
If one ‘R’ group is attached is a primary alcohol. If two ‘R’ groups, secondary alcohol. If
three ‘R’ groups, tertiary alcohol.
When using the IUPAC system to name alcohols, drop de –e ending and add the ending
o –ol.
Alcohols containing two, three or four –OH substituents are named: diols, triols,
and tetrols.
Phenols are compounds in which a hydroxyl group is attached directly to an
aromatic ring. Phenol is a parent compound. Phenols are used to make plastics,
fibers and drugs.
Alcohols are capable of intermolecular hydrogen bonding. They boil at
higher temperatures than alkanes and halocarbons. Alcohols are soluble. Alcohols
of up to 4 carbons are soluble in water in all proportions. The solubility of alcohols
with 4 or + carbons in the chain is usually much lower. Alcohols consist of 2 parts:
the carbon chain and the hydroxyl group. The carbon is nonpolar and the hydroxyl
group strongly polar.
Some alcohols: isopropyl (rubbing alcohol), ethylene glycol (ingredient of
anti-frezzes), glycerol (component of fats and oils).
Fermentation: production of ethanol from sugars by the actions of yeast
and bacteria.
o Breakdown of sugar glucose: pg. 733 (aprendan la formula)

Denatured alcohol: ethanol with an added substance to make it toxic.


Addition reaction: when a substance is added to the double or triple bond
of an alkyne or alkene. Addition reactions of alkenes are an important method of
introducing new functional groups into organic molecules.
Hydration reaction: the addition of water to an alkene.
Hydrogenation reaction: the addition of hydrogen to a carbon-carbon
double bond to produce an alkane. (Requires a catalyst). The hydrogenation of a
double bond is a reduction reaction.

Ethers.

Ether: compound in which oxygen is bonded to two carbon groups. The general
structure of an ether is R-O-R. The alkyl group attached to the ether linkage are
named in alphabetical order and are followed by the word ether.

23.3 Carbonyl Compounds

Carbonyl group: functional group with the general structure: 𝐶 ≡ 𝑂.


The: 𝐶 ≡ 𝑂 functional group is present in aldehydes and ketones.
Aldehyde: Organic compound in which the carbon of the carbonyl group is always
joined to at least one hydrogen. The general formula of an aldehyde is RCHO.
Ketone: organic compound in which the carbon of the carbonyl group is joined to 2
other carbons. The general formula is RCOR.
They don’t have hydroxyl groups. When the carbon chains of aldehydes and
ketones get longer its solubility decreases. Their boiling points are high.
They are isolated of plants and animals. They have fragrant and penetrating odors.
Aromatic aldehydes are often used as flavoring agents. Benzaldehyde is the
simplest aromatic aldehyde and it is also known as oil of bitter almond.
The simplest aldehyde is methanal, also called formaldehyde. Methanal is a 40%
aqueous solution known as formalin. Formalin can be used to preserve biological
specimens from decaying. But it causes cancer.
The most common industrial ketone is propanone also called acetone.

Carboxylic acids.

Carboxylic acid: compound with a carboxyl group. The general formula is RCOOH.
They are weak acids because they ionize slightly in solution to give a carboxylate
ion and a hydrogen ion. The carboxyl group in it is polar.
Carboxyl group: consists of a carbonyl group attached to a hydroxyl group.
Fatty acids: continuous-chain carboxylic acids that were isolated from fats.

Esters

Esters: derivatives of carboxylic acids in which the –OH of the carboxyl group has
been replaced by an –OR from an alcohol. Esters contain a carbonyl group and an
ether link to the carbonyl group. The general formula is RCOOR. They are prepared
from a carboxylic acid and an alcohol.
Dehydrogenation reaction: Loss of hydrogen. Dehydrogenation is an oxidation
reaction because the loss of each molecule of hydrogen involves the loss of two
electrons from the organic molecules.
Primary alcohols can be oxidized to aldehydes and secondary alcohols to ketones.
Tertiary alcohols cannot be oxidized.

23.4 Polymerization

Polymer: large molecule formed by the covalent bonding of repeating smaller


molecules. The smaller molecules that combine to form a polymer are called
monomers.
An addition polymer forms when unsaturated monomers react to form a polymer.
Condensation polymers are formed by a head-to-tail joining of monomer units.
Chapter 24 The Chemistry of life
24.1 A strategy of life

Two mayor cell types occur in nature: cells of bacteria (prokaryotic cells) and the
cells of all other organisms (eukaryotic cells). The prokaryotic cell is older.
One things that distinguish both of the cells from each other is that eukaryotic cells
have membrane- enclosed organelles. (Organelles are little organs, small
structures suspended in the cytoplasm. Eukaryotic cells have a nucleus and
prokaryotic cells don’t.
Photosynthesis: process in which light-capturing systems convert light energy into
chemical energy in the chloroplast. Photosynthesis uses the energy from sunlight
to reduce carbon dioxide to compounds that contain C-H bonds, mainly in the form
of glucose. (C6 H12 O6).
(Aprender la ecuación de este proceso.)

24.2 Carbohydrates

Carbohydrates: monomers and polymers of aldehydes and ketones that have


numerous hydroxyl groups attached; they are made up of carbon, hydrogen and
oxygen. Carbohydrates are present in most foods.
Monossacharides: Simplest carbohydrate molecules, simple sugars. Glucose and
fructose are examples of it.
Glucose is abundant in plants and animals.

Disaccharides and plyssacharides

The cyclic forms of 2 simple sugars can be linked by means of a condensation


reaction.
Disaccharide: a sugar that forms from 2 monosaccharides.
Polysaccharide: polymers produced by the linkage of many monosaccharide
monomers.

24.3 Amino acids and their Polymers

Amino Acid: any compound that contains an amino group and a carboxyl group in
the same molecule. Amino acids have a skeleton that consists of a carboxyl group
and an amino group, both which are covalently bonded to a central carbon atom.
The remaining 2 groups on the central carbon atom are hydrogen and an R group
that constitutes the amino acid side chain.

Peptides.

Peptide: any combination if amino acids in which the amino group of the one
amino acid is united with the carboxyl group of another amino acid.
The amide bonds between amino acids always involve the central amino and the
central carboxyl groups.

Proteins

Protein: a peptide with more than about 100 amino acids. Differences in the
chemical and physiological properties of peptides and proteins result from
differences in amino acid sequences.

Enzymes

Enzyme: proteins that act as biological catalysts. Enzymes increase the rates of
chemical reactions in living things.
Substrates: molecules on which an enzyme acts.
Active site: the place on an enzyme where a substrate binds.

24.4 Lipids

Lipids: fats, oils, and other water-insoluble compounds. Lipids tend to dissolve
readily in organic solvents, such as ether and chloroform, rather than in highly
polar solvents such as water. This property sets them apart from most biological
substances such as carbohydrates and proteins.
Triglyceride: long chain carboxylic acids.
Saponification: hydrolysis of oils and fats by boiling with an aqueous solution of an
alkali-metal hydroxide.
Phospholipids: lipids that contain phosphate groups. In water, phospholipids
spontaneously form a spherical double layer, called a lipid bilayer, in which
hydrophobic tails of phospholipid molecules are sandwiched between 2 layers of
hydrophilic heads.
Waxes: esters of long-chain fatty acids and long chain-alcohols.

(Estudiar el cuadro de acid, alcohol and odor. Está en el cuaderno)

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