FUNCTIONAL GROUP Flashcards
contain only carbon (C) and hydrogen (H); H can be replaced by other atoms or groups
HYDROCARBONS
The replacements are called ____________ and are reactive sites in molecules
- group of atoms that is largely responsible for the chemical behavior of the parent molecule
- units by which we divide organic compounds into families of compounds
- serve as the basis for naming organic compounds
- Determine in large measure the physical properties of a compound
- specific group of atoms that have a distinctive acid-base character, contribution to water solubility, and chemical reactivity
- Can influence the properties of adjacent functional groups and together define the physicochemical properties of the drug molecule
functional group
Different molecules containing the same kind of functional group or groups undergo similar reactions
TRUE
- Contain an OH (______) group bonded to a tetrahedral carbon into a family called ______
- Compounds containing a COOH (_______) belong to a family called ______
- hydroxyl
- alcohols
- carboxyl group
- carboxylic acids
enhances water solubility
-OH
alcohol
________: contain both acidic and basic functional groups
- the proton from the carboxylic acid binds to the basic amine producing a molecule with an overall net charge of zero termed as __________
- difficulty dissolving in aqueous environment such as the GIT tract
Effects: formulation and pharmacokinetics
- zwitter ion
AMPHOTERIC DRUGS
hydrocarbons
alkane
alkene
alkyne
simple oxygen heteroatomics
alcohol
ether
epoxide
carbonyl compounds
aldehyde
ketone
carboxylic acid
ester
amide
acyl halide
the rest of functional groups
haloalkane
thiol
arene
amine
nitrile
imine
azo compound
Single chain, no rings involved
aliphatic compounds
made up of only hydrogen and carbon
hydrocarbons
do not contain the benzene group, or the benzene ring
aliphatic hydrocarbon
- Alkanes are _______ hydrocarbons; that is, they contain only carbon-carbon ______ bonds.
— Has no rings of carbon atoms (_______) - A hydrocarbon that contains one or more carbon-carbon double bonds, triple bonds, or benzene rings is classified as an _______
- saturated hydrocarbons; single
— acyclic - unsaturated hydrocarbons
hydrocarbon that contains carbon atoms joined to form a ring
cyclic hydrocarbons
saturated hydrocarbon in which carbon atoms connected to one another in a cyclic (ring) arrangement are present
cycloalkanes
contain one or more benzene rings
aromatic compounds
formula of alkane
CnH2n+2
The three simplest alkanes
methane
ethane
propane
3D STRUCTURAL REPRESENTATIONS
DASH-WEDGE-LINE STRUCTURE
BALL-AND-STICK MODEL
SPACE-FILLING MODEL
_______ represent bonds receding behind the page, ______ bonds coming out of the page, and _______ bonds in the plane of the page.
- Dashes
- wedges
- solid lines
DASH-WEDGE-LINE STRUCTURE
This type of model emphasizes the connections (bonds) among the atoms and shows the tetrahedral arrangement of bonds about carbon atoms.
BALL-AND-STICK MODEL
This type of model emphasizes the overall shape of the molecule and shows the tetrahedral arrangement of bonds about carbon atoms.
SPACE-FILLING MODEL
2D STRUCTURAL REPRESENTATIONS
EXPANDED
CONDENSED
SKELETAL
LINE-ANGLE STRUCTURAL FORMULA
A structural formula that shows all atoms in a molecule and all bonds connecting the atoms.
EXPANDED STRUCTURAL FORMULA
A structural formula that uses grouping of atoms, in which central atoms and the atoms connected to them are written as a group.
CONDENSED STRUCTURAL
FORMULA
A structural formula that shows the arrangement and bonding of carbon atoms present but does not show the hydrogen atoms attached to the carbon atoms.
SKELETAL STRUCTURAL FORMULA
A structural formula in which a line represents a carbon-carbon bond and a carbon atom is understood to be present at every point where lines meet and at the ends of lines.
LINE-ANGLE STRUCTURAL FORMULA
General Formula of Cycloalkanes
CnH2n
Thus a given ______ contains two fewer hydrogen atoms than an alkane with the same number of hydrogen atoms
cycloalkane
Butane (C4H10) and cyclobutane (C4H8) are not isomers; isomers must have the same ___________
molecular formula
are generally used to represent cycloalkane structures
hexagon
o _______________ is a triangle
o _______________ is a square
o _______________ is a pentagon
o Cyclohexane is a hexagon
cyclopropane
cyclobutane
cyclopentane
Alkanes in which one or more hydrogen atoms have been replaced by a halogen atom
4 chemicals under alkyl halides
alkyl halides / haloalkanes
- CHCl3 - Chloroform
- CCl4 - Carbon Tetrachloride
- CH2Cl2 - Methylene Chloride
- Chlorofluorocarbons
- a volatile, sweet-tasting liquid that was used for many years as an anesthetic
- However, because of its toxicity (it can severely damage the liver, kidneys, and heart) it has been replaced by other compounds.
chloroform
also a toxic substance, serves as a cleaning liquid, for it removes grease stains
from clothing.
carbon tetrachloride
used as a solvent to decaffeinate coffee and as a paint remover
methylene chloride
Alkanes and cycloalkanes are ___________.
- The water insolubility of alkanes makes them ___________.
o prevent water from reaching the metal surface
o causing corrosion
o have biological functions as protective coatings.
- insoluble in water
- good preservatives for metal / non-polar
Alkanes and cycloalkanes have densities ______ than that of water.
- Alkane and cycloalkane densities fall in range _____ to _____, compared with water’s density of ___________
- When alkanes and cycloalkanes are mixed with water, two layers form (because of insolubility),
with the hydrocarbon layer on _____ (because of its lower density)
o This density difference between alkanes/cycloalkanes and water explains why oil spills in aqueous environments spread so quickly.
o the floating oil follows the movement of water.
- lower
- 0.6 - 0.8 g/mL
- 0.1 g/mL
- top
The boiling points of continuous-chain alkanes and cycloalkanes _____ with an ______ in carbon chain length or ring size.
- Continuous-Chain Alkanes
o The boiling point _____ roughly _____ for every carbon atom added to the chain as the result of increasing London force strength
— London forces become stronger as ________ area increases.
- increase, increase
- increase, 30*
- surface
____________ chain alkanes (1 to 4 carbon atoms) are _________ at room temperature
Short, continuous alkanes
gas
Continuous-chain alkanes containing 5 to 17 carbon atoms are _____, and alkanes that
have carbon chains longer than this are _____ at room temperature
- liquid
- solid
Branching alkanes
o Branching on a carbon chain ______ the boiling point of an alkane.
o Branched alkanes are more ______, with _______ areas than
their straight-chain isomers.
- decrease
- compact, smaller surface
o Cycloalkanes have ______ boiling points than their non-cyclic counterparts with the same number of carbon atoms
—- An important factor contributing to this effect is the _______ of carbon halogen bonds, which results in increased dipole-dipole interactions.
o __________ containing two or more chlorine atoms, bromoalkanes, and iodoalkanes are all more dense than water.
o ________ and ________ are gases at room temperature, and _________ through _________ are liquids at room temperature.
- higher
- polarity
- chloroalkanes
- cyclopropane & cyclobutane = gas
- cyclopentane & cyclooctane = liquid
A chemical reaction between a substance and oxygen (usually form air) that proceeds with the evolution of heat and light (usually as a flame)
Combustion
When sufficient oxygen is present to support _______, carbon dioxide and water are the products
total combustion (blue flame)
______, ______, ______: alkanes that undergo highly exothermic combus on
reac ons
natural gas, gasoline, fuel oil
o ________: used in home heating in rural areas and in gas barbecue units
o ________: fuels portable camping stoves
o ________: complex mixture of many alkanes and other types of hydrocarbons
- propane
- butane
- gasoline
can occur if insufficient oxygen is present during combus on
process
- Some carbon monoxide and/or elemental carbon are reaction products along with carbon dioxide (CO2)
- Appearance of deposits of carbon soot on the bottom of glassware is physical evidence that incomplete combustion is occurring.
- The problem is that the air-to-fuel ratio for the Bunsen burner is not correct
incomplete combustion (yellow flame)
- Chemical reacTIon between a substance and a halogen in which one or more halogen atoms are incorporated into molecules of the substance
- Produces a hydrocarbon derivative in which one or more halogen atoms have substituted for hydrogen atoms
- A chemical reaction in which part of a small reacting molecule replaces an atom or a group of
atoms on a hydrocarbon or hydrocarbon derivative - an alkane reaction of this is an example of ________
substitution
HALOGENATION
An R group can be an ___________: methyl, ethyl, propyl, etc. – or any number of other organic
groups.
Consider the symbol R to represent the REST of an organic molecule.
alkyl group
physical properties of alkanes and cycloalkanes
- solubility
- insoluble in water
- soluble in nonpolar solvents - density
- less dense than water
- float on top - boiling point
- increase as C chain length increases
- decrease when branching
chemical properties of alkanes and cycloalkanes
- combustion
- flammable
- combustion products are CO2 and water - halogenation
- H atoms replaced by halogens (substitution reaction)
- requires presence of heat/light
- Rules established by the Interna onal Union of Pure and Applied Chemistry (IUPAC)
- IUPAC name for an alkane with an unbranched chain of carbon atoms
- IUPAC name for an alkane with a branched chain of carbon atoms
The IUPAC System
- Older system of common nomenclature, the total number of carbon atoms in an alkane,
regardless of their arrangement, determine the name - Iso – branched chain
common names
____________: an atom or group of atoms a ached to a chain (or ring) of carbon atoms
susbtituent
For branched-chain alkanes, the substituents are specifically called ________
o An alkyl group is the group of atoms that would be obtained by removing a hydrogen atom from an alkane
o Hydrogen in an alkane is replaced by an OH, the compound becomes _______
o Replaced by an NH2, the compound becomes an ______
o Replaced by a halogen, the compound becomes an ________
o Replaced by an OR, the compound becomes an __________
The alkyl group name followed by the name of the class of the compound (alcohol, amine, etc.) yields the common name of the compound
- alkyl group
- alcohol
- amine
- alkyl halide
- ether
- The names of straight-chain alkyl groups o en have the prefix “n” (for normal) to emphasize that the
carbons are in unbranched chain. - Whenever the prefix “iso” is used, the iso structural unit is at one ed of the molecule, and any group replacing a hydrogen is at the other end
