Chapter 3 Review (for Exam 2): Organic Compounds - Alkanes and Their Stereochemistry
Alkanes are sometimes referred to as "paraffins", a word derived from Latin, meaning...
"little affinity".
A phosphate group has the general formula...
(OPO3 3-)
When naming acyclic aliphatic (non aromatic) aldehydes, we generally use the suffix...
-al
When naming amides, we use the suffix...
-amide
IUPAC prefers that amines be named with the suffix...
-amine
According to the rules of IUPAC nomenclature, ketones are named by changing the suffix -ane, of the parent alkane, to...
-anone
When naming compounds with an arene (a benzene derivative), we use the suffix...
-benzene (e.g. Chlorobenzene)
When naming alkenes (R2C=CR2), we use the suffix...
-ene (e.g. Ethene)
When naming ethers, we use generally use the suffix...
-ether (alkyl ether)
Naming esters requires using the suffix...
-oate
Carboxylic acids are named with the suffix...
-oic acid.
When naming carboxylic acid anhydrides, we use the suffix...
-oic anhydride
When naming alcohols we use the suffix...
-ol
If a compound is a natural product of carboxylic acid, to indicate which carbon atom is part of the aldehyde group, we use the infix...
-oxo- (C=O)
When naming ethers, we can also use infix...
-oxy- (alkoxyalkane)
When an acyl chloride functional group takes priority, acyl chlorides are named by taking the name of the parent carboxylic acid, and substituting ...
-oyl chloride
When naming sulfides with different substituents attached to the same sulfur, we use the infix...
-sulfanyl-
Thioesters, being the sulfur analogue to esters, use the naming suffix...
-thioate
The method for naming thiols is nearly identical to alcohols, but thiols are given the suffix...
-thiol (alkanethiol)
When naming alkynes (R-C≡C-R'), we use the suffix...
-yne (e.g. Ethyne)
A propane molecule substituted with a hydroxyl group on each carbon atom would be named...
1,2,3-tripropanol (or propan-1,2,3-triol)
A substituted, propane-derived, ketone compound with a carbonyl group on carbon 2 (higher priority), and a hydroxyl group on carbon 1 (lower priority), would be named...
1-hydroxy-2-propanone.
An eclipsing CH3-CH3 interaction has a torsional strain value of...
11kJ/mol
The eclipsed conformation of butane, where both methyl groups are eclipsed by H atoms, has a torsional strain of...
16kJ/mol (2 CH3-H interactions @ 6kJ/mol + 1 H-H interaction @ 4kJ/mol)
The eclipsed conformation of butane where the methyl groups eclipse each other, has a torsional strain value of...
19 kJ/mol (11kJ/mol for methyl-methyl + 2x methyl-H @ 6kJ/mol)
A pentane derived ketone with the carbonyl group on carbon 3, and a methyl group on carbons 2 and 4, would be named...
2,4-dimethyl-3-pentanone
A propane substituted with a sulfhydryl group on its second carbon would be given the name...
2-Propanethiol.
A substituted propane molecule with a carboxyl group on the first carbon (higher functional group) and a terminal carbonyl group on the last carbon (lower functional group), would be named...
3-oxopropanoic acid
A gauche CH3-CH3 interaction has a torsional strain value of...
3.8 kJ/mol
The torsional strain produced from a single H-H eclipsing interaction is equal to...
4kJ/mol (x3 in ethane = 12kJ/mol)
An eclipsing H-CH3 interaction has a torsional strain value of...
6 kJ/mol
The general formula name for amides is...
Alkanamide
Esters with both substituents being alkanes, have the general name formula...
Alkyl alkanoate
Disulfides with substituents that are different from each other, are given the general name formula...
Alkyl disulfanylalkane
A butyl group can be abbreviated...
Bu
After irradiating methane and Cl2 with UV light, the first products are...
CH3Cl and HCl
When naming sulfides with the same substituent bonded to the sulfur atom twice, the general naming form is...
Di(substituent) sulfide
The ether, Ethoxyethane, can also be given the name (and is more commonly known as)...
Diethyl ether.
A compound with two ethyl substituents bonded to the same sulfur would be named...
Diethyl sulfide.
A compound with two identical ethyl substituents bonded to a sulfinyl functional group (S=O) would be named...
Diethyl sulfoxide.
Disulfides with substituents that are the same, are given the general name formula...
Disubstituent disulfide.
Sulfoxides with two identical substituents have the general name formula...
Disubstituent sulfoxide.
An ethyl group can be abbreviated...
Et
The carboxylic acid anhydride of two ethanoic acid derivatives, is known as...
Ethanoic anhydride.
The acyl chloride derived from Ethanoic acid would be named...
Ethanoyl chloride.
An ester with its two substituents being an ethyl and a butyl group would be named...
Ethyl butanoate.
A methyl group can be abbreviated...
Me
Multiplier prefixes di-, tri-, tetra-, and so forth, should...
NOT be used when alphabetizing substituents.
Compounds that contain one or more electronegative halogen atoms bonded to a carbon atom are known as...
Organohalides (or Haloalkanes)
Alkanes are able to react with both...
Oxygen and halogens.
A propyl group can be abbreviated...
Pr
The amide of propanoic acid is...
Propanamide (CH3CH3C=O(NH2))
A primary amine with a bonded propyl substituent would be named...
Propylamine.
Carboxylic acids have the general formula...
R-COOH
The general formula for an alkyne is...
R-C≡C-R'
The general formula for an alcohol is...
R-OH
Organohalides (haloalkanes) have the general formula...
R-X
The general formula for an alkene is...
R2C=CR2
Ketones have the general formula...
R2C=O
An arene (phenyl group) has the general formula...
RC6H5 (or RPh)
Aldehydes have the general formula...
RCH=O
Amides have the general formula...
RCONR2 (R2 can be H2)
A carboxylic acid anhydride has the general formula...
RCOOCOR'
Esters have the general formula...
RCOOR'
Thioesters have the general formula...
RCOSR
Amines are classified as either primary, secondary, or tertiary, with the general formulas of...
RNH2, R2NH, and R3N, respectively.
Diphosphates have the general formula...
ROP2O6 3-
Monophosphates have the general formula...
ROPO3 2-
Ethers have the general formula...
ROR'
The general formula for thiols is...
RSH
Sulfides have the general formula...
RSR'
Disulfides have the general formula...
RSSR'
Sulfides are the sulfur analogue to ethers, and are thus sometimes termed...
Thioethers.
A tertiary amine with three bonded methyl groups would be named...
Trimethylamine
An acidic compound that contains a carboxyl group (C(O)OH) is known as...
a carboxylic acid
A compound that has two acyl groups (-RC=O-) bonded to a common oxygen atom is known as...
a carboxylic acid anhydride
A compound that has two organic groups bonded to two linked sulfur atoms, is known as...
a disulfide.
A compound that has two organic substituents bonded to the same carbonyl group (C=O) is known as...
a ketone.
The position of the carbonyl group of a ketone is denoted by...
a locant. (number)
A compound that has two organic substituents bonded to the same sulfur atom, is known as...
a sulfide.
The sulfur analogue to a carbonyl functional group (C=O) is known as...
a sulfinyl functional group (S=O)
A compound containing a sulfinyl functional group (S=O) attached to two carbons is known as...
a sulfoxide.
The sulfur analogue of alcohols, a compound that contains a carbon atom bonded to an electronegative Sulfhydryl functional group (SH) is known as...
a thiol.
When naming organohalides (haloalkanes) we can also use the the halide as the suffix, using the general naming formula...
alkyl halide. (substituted with actual halogen, e.g. Ethyl chloride)
Using the infix -sulfanyl-, the general naming formula for a sulfide is...
alkyl sulfanylalkane
Eclipsed conformation is the highest-energy conformer of a molecule since...
all C-H bonds are as close to each other as possible.
Staggered conformation is the lowest-energy conformer of a molecule since...
all C-H bonds are as far away from each other as possible.
Amines can also be named with the prefix...
amino-
A compound that has an acyl group bonded to a chloride is known as...
an acyl chloride (or acid chloride)
A carbonyl group (C=O) and an alkyl group (R ) combined, make up...
an acyl group.
A compound with a hydroxyl group bonded to an sp3 hybridized carbon is known as...
an alcohol
A compound that contains a terminal carbonyl group is known as...
an aldehyde.
A double bond acting as a functional group between two carbon atoms, forms a compound known as...
an alkene.
A triple bond acting as a functional group between two carbon atoms, forms a compound known as...
an alkyne.
If one of the carbons attached to an amine (RNH2, R2NH, R3N) is a carbonyl-group carbon (C=O), then the entire functional group is known as...
an amide
A derivative of ammonia, a compound that contains one or more organic substituents to an electronegative nitrogen atom, with a lone pair of electrons, is known as...
an amine.
Acting as a functional group, an alkyl-substituted benzene ring is known as either...
an arene or a phenyl group.
A compound, such as a disaccharide, that has two organic substituents bonded to the same electronegative oxygen atom is known as...
an ether.
Between staggered and eclipsed conformations exists...
an infinite number of conformations.
A sawhorse representation views a Carbon-Carbon bond at...
an oblique angle.
In butane, the lowest-energy arrangement is its...
anti conformation.
The anti conformation of butane involves the methyl groups...
being as far away from each other as possible. (180º)
An aldehyde derivative of butane would be named...
butanal
Alkanes show regular increases in both boiling point and melting point as...
chain length (molecular weight) increases.
Isomers with different conformations are known as...
conformational isomers.
Rotation around a single bond produces isomers with different...
conformations.
The decrease in melting and boiling point of branch-chained alkanes is due to...
decreased London dispersion forces. (molecules are less attracted to each other and thus transfer heat more easily)
A compound with two methyl groups attached to two linked sulfur atoms would be named...
dimethyl disulfide
A Newman projection views a Carbon-Carbon bond...
end-on
Chemical compounds derived from a carboxylic acid, in which one hydroxyl group is replaced by an -O-alkyl (alkoxy) group, are known as...
esters.
Phosphate groups of a disphosphate are linked via...
ether bonds. (O atoms)
When naming organohalides (haloalkanes) we us the prefix...
halo- (substituted with actual halogen, e.g. Chloro-)
When naming alcohols, if a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), we use the prefix...
hydroxy-
The stabilization of the staggered conformation, relative to the eclipsed one, of ethane, is due to the orbitals on one carbon...
interacting with the antiorbitals on the other carbon.
The reaction of an alkane with Cl2 occurs when a mixture of the two is...
irradiated with ultraviolet light
The more Carbon atoms a compound has, the larger the number of possible...
isomers.
Based on the functional groups of a given compound, we can predict both...
its properties and reactivity.
The energy barrier to rotation makes some conformational isomers...
lower in energy to others.
Compared to straight-chain alkanes, branched-chain alkanes have...
lower melting and boiling points.
A methyl substituent sharing the same oxygen with an ethyl substituent would be named...
methOXYethane.
A compound with a methyl group (lower substituent) and an ethyl group (parent chain) attached to two linked sulfur atoms would be named...
methyl disulfanylethane
For example, a compound with a sulfur atom bonded to both a methyl group (smaller substituent) and a pentyl group (larger substituent i.e. parent chain) would be named...
methyl sulfanylpentane
A compound with an alkyl group bonded to one of the O atoms of a phosphate group, is known as a...
monophosphate
The hyphenated and italicized prefixes sec- and tert- are...
not used for alphabetizing purposes.
In general, the weakly electronegative carbonyl carbon of an ester (electrophile), reacts with...
nucleophiles (groups with a tendency to donate electrons to electron-poor sites)
The symbol R is used throughout chemistry to indicate a generalized...
organic group.
A pentane substituted carboxylic acid would be named...
pentanoic acid.
When naming compounds with an arene (phenyl group), we can also use the prefix...
phenyl- (e.g. Phenylalanine)
Primary, secondary, and tertiary H atoms are attached to...
primary, secondary, and tertiary carbon atoms, respectively.
Alkanes are often described as...
saturated hydrocarbons.
Saturation refers to having the maximum number of Hydrogens per Carbon atom due to alkanes having only...
single bonds. (C-C and C-H)
Sulfoxides are oxidized derivatives of...
sulfides.
The hindered rotation around the Carbon-Carbon bonds of propane are due to...
the 14 kJ/mol rotational barrier of the molecule.
Citric acid is a tertiary alcohol because...
the carbon atom bonded to the hydroxyl functional group is also bonded to three other carbons.
Alcohols are classified as either primary, secondary, or tertiary, based upon the number of carbon atoms connected to...
the carbon atom that bears the hydroxyl group.
An anhydride is the compound obtained by removing...
the elements of water from an acid.
When naming compounds with a complex substituent, the complex substituent is treated as a whole and is alphabetized according to...
the first letter of its complete name
An alkyl group is the functional group that results from...
the removal of a H atom from an alkane.
The most favorable, lowest energy, conformation of an alkane is...
the straight-chain anti conformation.
Isomers are compounds that have the same numbers and kinds of atoms, but differ in ...
the way the atoms are arranged.
The product of esterification between a carboxylic acid (RCOOH) and a thiol (SH) is a...
thioester functional group
The extra 12kJ/mol of energy present in the eclipsed conformation of ethane is called...
torsional strain.
The nonhyphenated prefix iso- is...
used for alphabetizing purposes. (considered part of the alkyl-group name)