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(SLU) PHARMA 113: Chem Lec > FUNCTIONAL GROUP > Flashcards

FUNCTIONAL GROUP Flashcards

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1
Q

contain only carbon (C) and hydrogen (H); H can be replaced by other atoms or groups

A

HYDROCARBONS

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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

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3
Q

Different molecules containing the same kind of functional group or groups undergo similar reactions

A

TRUE

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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
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5
Q

enhances water solubility

A

-OH

alcohol

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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

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7
Q

hydrocarbons

A

alkane
alkene
alkyne

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8
Q

simple oxygen heteroatomics

A

alcohol
ether
epoxide

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9
Q

carbonyl compounds

A

aldehyde
ketone
carboxylic acid
ester
amide
acyl halide

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10
Q

the rest of functional groups

A

haloalkane
thiol
arene

amine
nitrile
imine
azo compound

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11
Q

Single chain, no rings involved

A

aliphatic compounds

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12
Q

made up of only hydrogen and carbon

A

hydrocarbons

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13
Q

do not contain the benzene group, or the benzene ring

A

aliphatic hydrocarbon

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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
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15
Q

hydrocarbon that contains carbon atoms joined to form a ring

A

cyclic hydrocarbons

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16
Q

saturated hydrocarbon in which carbon atoms connected to one another in a cyclic (ring) arrangement are present

A

cycloalkanes

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17
Q

contain one or more benzene rings

A

aromatic compounds

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18
Q

formula of alkane

A

CnH2n+2

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19
Q

The three simplest alkanes

A

methane
ethane
propane

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20
Q

3D STRUCTURAL REPRESENTATIONS

A

DASH-WEDGE-LINE STRUCTURE
BALL-AND-STICK MODEL
SPACE-FILLING MODEL

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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

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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

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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

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24
Q

2D STRUCTURAL REPRESENTATIONS

A

EXPANDED
CONDENSED
SKELETAL
LINE-ANGLE STRUCTURAL FORMULA

25
Q

A structural formula that shows all atoms in a molecule and all bonds connecting the atoms.

A

EXPANDED STRUCTURAL FORMULA

26
Q

A structural formula that uses grouping of atoms, in which central atoms and the atoms connected to them are written as a group.

A

CONDENSED STRUCTURAL
FORMULA

27
Q

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.

A

SKELETAL STRUCTURAL FORMULA

28
Q

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.

A

LINE-ANGLE STRUCTURAL FORMULA

29
Q

General Formula of Cycloalkanes

A

CnH2n

30
Q

Thus a given ______ contains two fewer hydrogen atoms than an alkane with the same number of hydrogen atoms

A

cycloalkane

31
Q

Butane (C4H10) and cyclobutane (C4H8) are not isomers; isomers must have the same ___________

A

molecular formula

32
Q

are generally used to represent cycloalkane structures

A

hexagon

33
Q

o _______________ is a triangle
o _______________ is a square
o _______________ is a pentagon
o Cyclohexane is a hexagon

A

cyclopropane
cyclobutane
cyclopentane

34
Q

Alkanes in which one or more hydrogen atoms have been replaced by a halogen atom

4 chemicals under alkyl halides

A

alkyl halides / haloalkanes

  1. CHCl3 - Chloroform
  2. CCl4 - Carbon Tetrachloride
  3. CH2Cl2 - Methylene Chloride
  4. Chlorofluorocarbons
35
Q
  • 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.
A

chloroform

36
Q

also a toxic substance, serves as a cleaning liquid, for it removes grease stains
from clothing.

A

carbon tetrachloride

37
Q

used as a solvent to decaffeinate coffee and as a paint remover

A

methylene chloride

38
Q

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.

A
  • insoluble in water
  • good preservatives for metal / non-polar
39
Q

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.

A
  • lower
  • 0.6 - 0.8 g/mL
  • 0.1 g/mL
  • top
40
Q

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.

A
  • increase, increase
  • increase, 30*
  • surface
41
Q

____________ chain alkanes (1 to 4 carbon atoms) are _________ at room temperature

A

Short, continuous alkanes

gas

42
Q

Continuous-chain alkanes containing 5 to 17 carbon atoms are _____, and alkanes that
have carbon chains longer than this are _____ at room temperature

A
  • liquid
  • solid
43
Q

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.

A
  • decrease
  • compact, smaller surface
44
Q

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.

A
  • higher
  • polarity
  • chloroalkanes
  • cyclopropane & cyclobutane = gas
  • cyclopentane & cyclooctane = liquid
45
Q

A chemical reaction between a substance and oxygen (usually form air) that proceeds with the evolution of heat and light (usually as a flame)

A

Combustion

46
Q

When sufficient oxygen is present to support _______, carbon dioxide and water are the products

A

total combustion (blue flame)

47
Q

______, ______, ______: alkanes that undergo highly exothermic combus on
reac ons

A

natural gas, gasoline, fuel oil

48
Q

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

A
  • propane
  • butane
  • gasoline
49
Q

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
A

incomplete combustion (yellow flame)

50
Q
  • 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 ________
A

substitution

HALOGENATION

51
Q

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.

A

alkyl group

52
Q

physical properties of alkanes and cycloalkanes

A
  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
Q

chemical properties of alkanes and cycloalkanes

A
  1. combustion
    - flammable
    - combustion products are CO2 and water
  2. halogenation
    - H atoms replaced by halogens (substitution reaction)
    - requires presence of heat/light
54
Q
  • 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
A

The IUPAC System

55
Q
  • Older system of common nomenclature, the total number of carbon atoms in an alkane,
    regardless of their arrangement, determine the name
  • Iso – branched chain
A

common names

56
Q

____________: an atom or group of atoms a ached to a chain (or ring) of carbon atoms

A

susbtituent

57
Q

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

A
  • alkyl group
  • alcohol
  • amine
  • alkyl halide
  • ether
58
Q
  • 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
A

(SLU) PHARMA 113: Chem Lec (13 decks)

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