FUNCTIONAL GROUP Flashcards
1
Q
contain only carbon (C) and hydrogen (H); H can be replaced by other atoms or groups
A
HYDROCARBONS
2
Q
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
A
functional group
3
Q
Different molecules containing the same kind of functional group or groups undergo similar reactions
A
TRUE
4
Q
- Contain an OH (______) group bonded to a tetrahedral carbon into a family called ______
- Compounds containing a COOH (_______) belong to a family called ______
A
- hydroxyl
- alcohols
- carboxyl group
- carboxylic acids
5
Q
enhances water solubility
A
-OH
alcohol
6
Q
________: 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
A
- zwitter ion
AMPHOTERIC DRUGS
7
Q
hydrocarbons
A
alkane
alkene
alkyne
8
Q
simple oxygen heteroatomics
A
alcohol
ether
epoxide
9
Q
carbonyl compounds
A
aldehyde
ketone
carboxylic acid
ester
amide
acyl halide
10
Q
the rest of functional groups
A
haloalkane
thiol
arene
amine
nitrile
imine
azo compound
11
Q
Single chain, no rings involved
A
aliphatic compounds
12
Q
made up of only hydrogen and carbon
A
hydrocarbons
13
Q
do not contain the benzene group, or the benzene ring
A
aliphatic hydrocarbon
14
Q
- 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 _______
A
- saturated hydrocarbons; single
— acyclic - unsaturated hydrocarbons
15
Q
hydrocarbon that contains carbon atoms joined to form a ring
A
cyclic hydrocarbons
16
Q
saturated hydrocarbon in which carbon atoms connected to one another in a cyclic (ring) arrangement are present
A
cycloalkanes
17
Q
contain one or more benzene rings
A
aromatic compounds
18
Q
formula of alkane
A
CnH2n+2
19
Q
The three simplest alkanes
A
methane
ethane
propane
20
Q
3D STRUCTURAL REPRESENTATIONS
A
DASH-WEDGE-LINE STRUCTURE
BALL-AND-STICK MODEL
SPACE-FILLING MODEL
21
Q
_______ represent bonds receding behind the page, ______ bonds coming out of the page, and _______ bonds in the plane of the page.
A
- Dashes
- wedges
- solid lines
DASH-WEDGE-LINE STRUCTURE
22
Q
This type of model emphasizes the connections (bonds) among the atoms and shows the tetrahedral arrangement of bonds about carbon atoms.
A
BALL-AND-STICK MODEL
23
Q
This type of model emphasizes the overall shape of the molecule and shows the tetrahedral arrangement of bonds about carbon atoms.
A
SPACE-FILLING MODEL
24
Q
2D STRUCTURAL REPRESENTATIONS
A
EXPANDED
CONDENSED
SKELETAL
LINE-ANGLE STRUCTURAL FORMULA
25
A structural formula that shows all atoms in a molecule and all bonds connecting the atoms.
EXPANDED STRUCTURAL FORMULA
26
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
27
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
28
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
29
General Formula of Cycloalkanes
CnH2n
30
Thus a given ______ contains two fewer hydrogen atoms than an alkane with the same number of hydrogen atoms
cycloalkane
31
Butane (C4H10) and cyclobutane (C4H8) are not isomers; isomers must have the same ___________
molecular formula
32
are generally used to represent cycloalkane structures
hexagon
33
o _______________ is a triangle
o _______________ is a square
o _______________ is a pentagon
o Cyclohexane is a hexagon
cyclopropane
cyclobutane
cyclopentane
34
Alkanes in which one or more hydrogen atoms have been replaced by a halogen atom
4 chemicals under alkyl halides
alkyl halides / haloalkanes
1. CHCl3 - Chloroform
2. CCl4 - Carbon Tetrachloride
3. CH2Cl2 - Methylene Chloride
4. Chlorofluorocarbons
35
- 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
36
also a toxic substance, serves as a cleaning liquid, for it removes grease stains
from clothing.
carbon tetrachloride
37
used as a solvent to decaffeinate coffee and as a paint remover
methylene chloride
38
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
39
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
40
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
41
____________ chain alkanes (1 to 4 carbon atoms) are _________ at room temperature
Short, continuous alkanes
gas
42
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
43
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
44
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
45
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
46
When sufficient oxygen is present to support _______, carbon dioxide and water are the products
total combustion (blue flame)
47
______, ______, ______: alkanes that undergo highly exothermic combus on
reac ons
natural gas, gasoline, fuel oil
48
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
49
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)
50
* 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
51
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
52
physical properties of alkanes and cycloalkanes
1. solubility
- insoluble in water
- soluble in nonpolar solvents
2. density
- less dense than water
- float on top
3. boiling point
- increase as C chain length increases
- decrease when branching
53
chemical properties of alkanes and cycloalkanes
1. combustion
- flammable
- combustion products are CO2 and water
2. halogenation
- H atoms replaced by halogens (substitution reaction)
- requires presence of heat/light
54
* 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
55
* 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
56
____________: an atom or group of atoms a ached to a chain (or ring) of carbon atoms
susbtituent
57
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
58
- 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
