Shared Flashcard Set

Details

Chapter 3: Organic Compounds: Alkanes and Their Stereochem
Part of OCHEM Test 1
225
Organic Chemistry
Undergraduate 2
06/05/2017

Additional Organic Chemistry Flashcards

 


 

Cards

Term
functional groups
Definition
groups of atoms within a molecule that have a characteristic chemical behavior
Term
the chemistry of every organic molecule is determined by...
Definition
its functional groups
Term
3 categories functional groups can be categorized into
Definition
-those w/ C-C multiple bonds
-those in which C forms a single bond with an enegative atom
-those w/ C=O 2bl bond
Term
alkanes are formed by...
Definition
ovrlap of C sp3 orbitals
Term
alkanes are described as...
Definition
saturated hydrocarbons
Term
why alkanes are hydrocarbons
Definition
because they contain only C and H
Term
why alkanes are saturated
Definition
because all bonds are single
Term
the general formula for alkanes
Definition
CnH2n+2
Term
straight-chain alkane
Definition
alkane w/ all the C's in a row
Term
branched-chain alkane
Definition
alkane that has a branched C chain
Term
constitutional isomers
Definition
isomers whose atoms are connected differently
Term
do constitutional isomers have different properties?
Definition
alwauys
Term
straight-chain alkanes are named according to...
Definition
# of C's in their C chain
Term
alkyl group
Definition
the partial structure that results from the removal of 1 H from an alkane
Term
how alkyl groups are named
Definition
by replacing -ane with -yl
Term
n-alkyl group
Definition
formed by removal of an H atom from the end of a straight-chain alkane
Term
branched-chain alkyl groups
Definition
formed by removing an H from an internal C
Term
the prefixes sec- and tert- refer to...
Definition
the number of other C atom attached to the branching C atom
Term
sec-
Definition
secondary (2 C's attached to the branching C)
Term
tert-
Definition
tertiary (3 C's attached to the branching C)
Term
the possible degrees of alkyl substitution for C
Definition
-primary
-2ndary
-tertiary
-quarternary
Term
primary C
Definition
bonded to 1 other C
Term
secondary C
Definition
bonded to 2 other C's
Term
tertiary C
Definition
bonded to 3 other C's
Term
quarternary C
Definition
bonded to 4 other C's
Term
R
Definition
this symbol refers to the rest of the molecule
Term
primary H's
Definition
bonded to primary C's
Term
secondary H's
Definition
bonded to secondary C's
Term
tertiary H's
Definition
bonded to tertiary C's
Term
the system of nomenclature used in this book for naming alkanes
Definition
IUPAC system
Term
the components of a chemical name in the IUPAC system
Definition
-locant
-prefix
-parent
-suffix
Term
locant
Definition
shows the location of substituents and functional groups
Term
prefix
Definition
indicates the type of constituent or functional group
Term
parent
Definition
# of C's in the principal chain
Term
suffix
Definition
identifies functional group family
Term
how to name an alkane
Definition
1: find the parent hydrocarbon
2: number the atoms in the parent chain
3: identify and number the substituents
4: write the name as a single word
5: name a complex substituent as if it was a compound, and set it off in parentheses
Term
how to find the parent hydrocarbon in an alkane
Definition
1: find the longest continuous chain of C's, and use its name as the parent name
2: if 2 chains have the same number of C's, choose the one with more branch points
Term
how to number the atoms in the parent chain
Definition
1: start numbering at the end nearer the 1st branch point
2: if branching occurs an equal distance from both ends, begin numbering at the end nearer the second branch point
Term
how to identify and number the substituents
Definition
1: give each substituent a number that corresponds to its number on the parent chain
2: 2 substituents on the same C receive the same #
Term
how to write the name as a single word
Definition
1: use hyphens to separate prefixes and commas to separate numbers
2: use the prefixes di-, tri-, and tetra- if necessary, but don't use them for alphabetizing
Term
how to name a complex substituent as if it was a compound and set it off within parentheses
Definition
1: some simple branched-chain alkyl groups have common names
2: the prefix iso- is used for alphabetixing, but sec- and tert- are not
Term
some properties of alkanes
Definition
-alkanes are chemically inert to most laboratory reagents -alkanes react with O2 (combustion) and Cl2 (substitution) -the boiling and melting points of alkanes increase with increasing molecular weight -increased branching lowers an alkane's boiling point
Term
reactivity of alkanes to most laboratory reagents
Definition
chemically inert
Term
rxn of alkanes with O2
Definition
combustion
Term
rxn of alkanes with Cl2
Definition
substitution
Term
boiling and melting points of alkanes vs. molecular weight
Definition
directly proportional
Term
why the boiling and melting poiunts of alkanes increase with increasing molecular weight
Definition
weak dispersion forces
Term
strength of dispersion forces vs. molecular weight
Definition
directly proportional
Term
branching vs. an alkane's boiling point
Definition
the more branching, the higher the boiling point
Term
some straight-chain alkanes
Definition
-ethane
-propane
-butane
Term
stereochemistry
Definition
the branch of chemistry concerned with the 3D aspects of molecules
Term
conformations of ethane
Definition
photograph figure 3-5
Term
what produces isomers of ethane at different conformation?
Definition
rotation about a single bond
Term
2 ways isomers can be represented
Definition
-sawhorse representations
-Newman projections
Term
sawhorse representation
Definition
views the C-C bond at an oblique angle
Term
Newman projection
Definition
views the C-C bond end-on-end and represents the 2 C's as a circle
Term
staggered conformation
Definition
the lowest energy conformation

occurs when all C-H bonds are as far from each other as possible (H's not lining up with each other)
Term
eclipsed conformation
Definition
the highest energy conformation

occurs when all the C-H bonds are as close to each other as possible (H's lining up with each other)
Term
the energy difference in staggered conformation is due to...
Definition
torsional strain from interactions between C-H bonding orbitals on one C and C-H bonding antibonding orbitals on an adjacent C, stabilizing the staggered conformation
Term
torsional strain
Definition
the extra energy in eclipsed conformation
Term
graph showing potential energy vs. angle of rotation
Definition
photograph figure 3-7
Term
conformations of propane
Definition
photograph figure 3-8
Term
conformations of butane
Definition
photograph the conformations in section 3.7
Term
the lowest energy conformation of butane occurs when...
Definition
the 2 large methyl groups are as far from each other as possible
Term
gauche conformation of butane
Definition
when 2 methyl groups are 60 degrees apart
Term
the energy difference in different conformations of molecules is due to...
Definition
steric strain
Term
steric strain
Definition
the repulsive interaction that results from forcing atoms to be closer together than their atomic radii allow
Term
the highest energy conformations of butane occur when...
Definition
the 2 methyl groups are eclipsed
Term
the most favored conformation for any straight-chain alkane
Definition
has C-C bonds in staggered arrangements and large substituents anti to each other
Term
the conformation adopted by most molecules
Definition
the most stable conformation
Term
the 5 parts to every name when naming organic molecules
Definition
1: stereoisomerism
2: substituents
3: parent
4: unsaturation
5: functional group
Term
stereoisomerism
Definition
indicates whether 2bl bonds are cis/trans and indicates stereocenters (R,S)
Term
substituents
Definition
groups connected to the main chain
Term
parent
Definition
the main chain
Term
unsaturation
Definition
identifies whether there are any 2bl or triple bonds
Term
functional group
Definition
the group after which the compound is named
Term
why you must name an organic molecule starting with the functional group
Definition
because the position of the functional group affects which parent chain you chose
Term
alkene (double bond) functional group
Definition
R2C=CR2
Term
R2C=CR2
Definition
alkene (double bond) functional group
Term
alkane (triple bond) functional group
Definition
RCCR
Term
RCCR
Definition
alkane (triple bond) functional group
Term
arene (aromatic ring) functional group
Definition
6 trigonal planar C's in a ring
Term
6 trigonal planar C's in a ring
Definition
arene (aromatic ring) functional group
Term
halide functional group
Definition
R-X

X = halogen
Term
R-X

X = halogen
Definition
halide functional group
Term
alcohol functional group
Definition
R-OH
Term
R-OH
Definition
alcohol functional group
Term
ether functional group
Definition
R-O-R
Term
R-O-R
Definition
ether functional group
Term
monophosphate functional group
Definition
R-PO42-
Term
R-PO42-
Definition
monophosphate functional group
Term
diphosphate functional group
Definition
R-P2O73-
Term
R-P2O73-
Definition
diphosphate functional group
Term
amine functional group
Definition
R-NH2
Term
R-NH2
Definition
amine functional group
Term
imine (Schiff base) functional group
Definition
R=NH
Term
R=NH
Definition
imine (Schiff base) functional group
Term
nitrile functional group
Definition
RN

the bond is a triple bond
Term
RN

the bond is a triple bond
Definition
nitrile functional group
Term
thiol functional group
Definition
R-SH
Term
R-SH
Definition
thiol functional group
Term
sulfide functional group
Definition
R-S-R
Term
R-S-R
Definition
sulfide functional group
Term
disulfide functional group
Definition
R-S-S-R
Term
R-S-S-R
Definition
disulfide functional group
Term
sulfoxide functional group
Definition
R2-S+-O-
Term
R2-S+-O-
Definition
sulfoxide functional group
Term
aldehyde functional group
Definition
[image]
Term
[image]
Definition
aldehyde functional group
Term
ketone functional group
Definition
[image]
Term
[image]
Definition
ketone functional group
Term
carboxylic acid functional group
Definition
[image]
Term
[image]
Definition
carboxylic acid functional group
Term
ester functional group
Definition
[image]
Term
[image]
Definition
ester functional group
Term
thioester functional group
Definition
[image]
Term
[image]
Definition
thioester functional group
Term
amide functional group
Definition
[image]
Term
[image]
Definition
amide functional group
Term
acid chloride functional group
Definition
[image]
Term
[image]
Definition
acid chloride functional group
Term
carboxylic acid anhydride functional group
Definition
[image]
Term
[image]
Definition
carboxylic acid anhydride functional group
Term
suffix associated with alkene
(double bond) functional group
Definition
-ene
Term
suffix associated with alkyne (triple bond) functional group
Definition
-yne
Term
suffix associated with arene (aromatic ring) functional group
Definition
none
Term
suffix associated with halide functional group
Definition
none
Term
suffix associated with alcohol functional group
Definition
-ol
Term
suffix associated with ether functional group
Definition
ether
Term
suffix associated with monophosphate functional group
Definition
phosphate
Term
suffix associated with diphosphate functional group
Definition
diphosphate
Term
suffix associated with amine functional group
Definition
-amine
Term
suffix associated with imine (Schiff base) functional group
Definition
none
Term
suffix associated with nitrile functional group
Definition
-nitrile
Term
suffix associated with thiol functional group
Definition
-thiol
Term
suffix associated with sulfide functional group
Definition
sulfide
Term
suffix associated with disulfide functional group
Definition
disulfide
Term
suffix associated with sulfoxide functional group
Definition
sulfoxide
Term
suffix associated with aldehyde functional group
Definition
-al
Term
suffix associated with ketone functional group
Definition
-one
Term
suffix associated with carboxylic acid functional group
Definition
-oic acid
Term
suffix associated with ester functional group
Definition
-oate
Term
suffix associated with thioester functional group
Definition
-thioate
Term
suffix associated with amide functional group
Definition
-amide
Term
suffix associated with acid chloride functional group
Definition
-oyl chloride
Term
suffix associated with carboxylic acid anhydride functional group
Definition
-oic anhydride
Term
suffix to use when there's no functional group involved
Definition
put an e at the end of it
Term
when naming the parent chain, meth means...
Definition
1 C atom in the alkane or parent chain
Term
when naming an alkane or the parent chain, eth means...
Definition
2 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, prop means...
Definition
3 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, but means...
Definition
4 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, pent means...
Definition
5 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, hex means...
Definition
6 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, hept means...
Definition
7 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, oct means...
Definition
8 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, non means...
Definition
9 C atoms in the alkane or parent chain
Term
when naming an alkane or the parent chain, dec means...
Definition
10 C atoms in the alkane or parent chain
Term
methane
Definition
alkane or parent chain with 1 C atom
Term
ethane
Definition
alkane or parent chain with 2 C atoms
Term
propane
Definition
alkane or parent chain with 3 C atoms
Term
butane
Definition
alkane or parent chain with 4 C atoms
Term
pentane
Definition
alkane or parent chain with 5 C atoms
Term
hexane
Definition
alkane or parent chain with 6 C atoms
Term
heptane
Definition
alkane or parent chain with 7 C atoms
Term
octane
Definition
alkane or parent chain with 8 C atoms
Term
nonane
Definition
alkane or parent chain with 9 C atoms
Term
decane
Definition
alkane or parent chain with 10 C atoms
Term
methyl
Definition
methane with one H replaced by R
Term
ethyl
Definition
ethane with 1 H replaced by R
Term
propyl
Definition
propane with 1 H replaced by R
Term
butyl
Definition
butane with 1 H replaced by R
Term
pentyl
Definition
pentane with 1 H replaced by R
Term
hexyl
Definition
hexane with 1 H replaced by R
Term
heptyl
Definition
heptane with 1 H replaced by R
Term
octyl
Definition
octane with 1 H replaced by R
Term
nonyl
Definition
nonane with 1 H replaced by R
Term
decyl
Definition
decane with 1 H replaced by R
Term
when there is a double bond, should the parent chain include the double bond?
Definition
yes
Term
when there is no double bond, but there is a functional group attached, should the parent chain include the C next to the functional group?
Definition
yes
Term
depiction of propyl
Definition
[image]

attached to the end C
Term
[image]
Definition
propyl
Term
depiction of isopropyl
Definition
[image]

attached to the middle C
Term
[image]
Definition
isopropyl
Term
isobutane
Definition
[image]
Term
[image]
Definition
isobutane
Term
depiction of butyl
Definition
[image]

here, it's connected to a Cl
Term
[image]
Definition
butyl
Term
sec-butyl
Definition
[image]

notice the Cl is attached to the secondary C
Term
[image]
Definition
sec-butyl
Term
tert-butyl
Definition
[image]

notice the R is attached to the tertiary C
Term
[image]
Definition
tert-butyl
Term
primary C
Definition
bonded to 1 R
Term
secondary C
Definition
bonded to 2 R
Term
tertiary C
Definition
bonded to 3 R
Term
quarternary C
Definition
bonded to 4 R
Term
what R is used for
Definition
to represent a generalized organic group
Term
what characters to use to indicate whether a C is primary, 2ndary, tertiary, or quarternary
Definition
p
s
t
q
Term
is an H bonded to a primary C primary, secondary, or tertiary?
Definition
primary
Term
is an H bonded to a secondary C primary, secondary, or tertiary?
Definition
secondary
Term
is an H bonded to a tertiary C primary, secondary, or tertiary?
Definition
tertiary
Term
the template for the name of an alkane
Definition
locant-prefix-parent-suffix
Term
what the locant in the name of an alkane is supposed to indicate
Definition
where the substituents and functional groups are
Term
what the prefix in the name of an alkane is supposed to indicate
Definition
what the substituents are
Term
what the parent in the name of an alkane is supposed to indicate
Definition
how many carbons in alkane
Term
what the suffix in the name of an alkane is supposed to indicate
Definition
primary functional group
Term
if 2 hydrocarbon chains of equal length have different numbers of branch points, which hydrocarbon chain is the parent?
Definition
the one with more branch points
Term
when numbering the C's in the hydrocarbon chain, where should you begin?
Definition
at end nearer to the first branch point
Term
when numbering the hydrocarbons in a molecule with branching an equal distance away from the parent chain, where should you begin?
Definition
at the end nearer to the 2nd branch point
Term
order to list substituents when naming an alkane
Definition
alphabetical order
Term
how a substituent that is itself branched is included in the name of an alkane
Definition
1: numbered beginning at its point of attachment to the main chain
2: it is then set off in parentheses
Term
why a positive charge can be an indicator of acidity
Definition
because having the positive charge, it's more like hydronium
Term
what arrows in acid-base reactions indicate
Definition
mechanisms
Term
what do you compare when comparing bases?
Definition
stability of the electrons on each base
Term
number of resonance forms vs. stability of an anion
Definition
the more resonance forms, the more stable
Term
the only intermolecular force that deals with nonpolar molecules
Definition
London forces
Term
London forces
Definition
intermolecular forces that occur as the result of induced dipoles between molecules

induced dipoles occur as the result of an instantaneous uneven distribution of electrons
Term
how the size of the molecule's electron cloud affects London forces
Definition
the bigger the electron cloud, the easier it is to distort the London forces into greases
Term
polarizeability vs. strength of London forces
Definition
directly proportional
Term
what branching of molecule does to boiling point
Definition
general rule of thumb: branching tends to lower the boiling point
Term
how the shape of different isomers of the same compound can affect boiling point
Definition
the more spherical the molecule, the lower the boiling point due to less area of overlap between adjacent molecules and weaker London forces
Term
dipole-dipole forces
Definition
positive end of a bond on one molecule being attracted to the negative end of a bond on another molecule
Term
H-bond
Definition
a dipole-dipole force between a proton attached to an N or O and an O or N

this isn't a bond; it's an association or attraction
Term
in an organic molecule, a functional group is...
Definition
a group of atoms that isn't a sp3 hybridized CH group
Term
constitutional isomer
Definition
isomers that have their atoms connected in a different order
Term
amount of substitution arount a bond vs. amount of strain
Definition
the more substitution around a bond, the more strain
Supporting users have an ad free experience!