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Chemistry Exam #3
Terms in this set (78)
Organic Chem (Beginning of Ch.12)
The study of the chemistry of carbon compounds
The study of the chemistry of all other elements
Any family of compounds in which adjacent members differ from each other by a definite factor
Alkane (saturated hydrocarbon)
A hydrocarbon with only carbon-to-carbon single bonds and existing as a continuous chain of carbon atoms also bonded to hydrogen atoms
Compounds having the same molecular formula but different structural formulas and properties
A continuous (unbranched) chain of carbon atoms
Also called normal alkanes
A chemical formula that shows how the atoms of a molecule are attached to one another
Condensed Structural Formula
An organic chemical formula that shows the hydrogen atoms (or other atoms or groups) right next to the carbon atoms to which they are attached
An organic chemical formula in which carbon atoms are implied at the corners and ends of lines.
Each carbon atom is understood to be attached to enough hydrogen atoms to give each carbon atom four bonds.
IUPAC System of Nomenclature
A systematic way of naming chemical substances so that each has a unique name
A hydrocarbon group derived from an alkane by removal of a hydrogen atom
IUPAC Rules for naming alkanes:
Name alkanes according to the LCC (longest continuous chain) of carbon atoms in the molecule (rather than the total number of carbon atoms).
If the hydrocarbon is branched, number the carbon atoms of the LCC.
Place the names of the substituent groups in alphabetical order before the name of the parent compound.
Chemical Properties of Alkanes
nonpolar and neither positive ions nor negative ions are attracted to a nonpolar molecule.
generally unreactive toward laboratory acids, bases, oxidizing agents, and reducing agents.
react with oxygen (combustion) and with halogens (halogenation
A hydrocarbon in which one or more hydrogen atoms has been replaced by a halogen atom
Alkyl Halide (haloalkane)
A compound resulting from the replacement of a hydrogen atom of an alkane with a halogen atom.
Common names of alkyl halides
the name of the alkyl group plus the stem of the name of the halogen, with the ending -ide
The IUPAC system uses the name of the parent alkane with a prefix indicating the halogen substituents, preceded by number indicating the substituent's location
The prefixes are fluoro-, chloro-, bromo-, and iodo-
A hydrocarbon with a ring of carbon atoms
A cyclic hydrocarbon with only single bonds
Naming Cycloalkanes (End of Ch.12)
named by adding the prefix cyclo- to the name of the open-chain compound having the same number of carbon atoms as there are in the ring
The properties of cyclic hydrocarbons are similar to those of the corresponding open-chain compounds
Unsaturated hydrocarbon (Beginning of Ch.13)
An alkene or alkyne having one or more multiple (double or triple) bonds between carbon atoms.
Alkene: A hydrocarbon with one or more carbon-carbon double bonds.
Alkyne: A hydrocarbon with a carbon-carbon triple bond
Rules for naming alkenes from the International Union and Pure and Applied Chemistry (IUPAC)
The longest chain of carbon atoms containing the double bond is considered the parent chain.
It is named using the same stem as the alkane having the same number of carbon atoms but ends in -ene to identify it as an alkene.
If there are four or more carbon atoms in a chain, we must indicate the position of the double bond.
The carbons atoms are numbered so that the first of the two that are doubly bonded is given the lower of the two possible numbers.
Substituent groups are named as with alkanes, and their position is indicated by a number.
An isomer in which two substituent groups are attached on the same side of a double bond or ring in an organic molecule
An isomer in which two substituent groups are attached to opposite sides of a double bond or ring in a molecule
Cis-Trans Isomers (geometric isomers)
Isomers that have different configurations because of the presence of a rigid structure such as a double bond or ring.
The two requirements for cis-trans isomerism are:
Rotation must be restricted in the molecule.
There must be two nonidentical groups on each doubly bonded carbon atom.
Physical Properties of Alkenes
The boiling points of straight-chain alkenes increase with increasing molar mass, just as with alkanes.
Insoluble in water but soluble in organic solvents.
A reaction in which substituent groups join to hydrocarbon molecules at points of unsaturation—the double or triple bonds
A reaction in which hydrogen gas reacts at a carbon-to-carbon double or triple bond or a carbon-to-oxygen double bond to add hydrogen atoms to carbon atoms.
A reaction in which a halogen reacts at a carbon-to-carbon double or triple bond to add halogen atoms to carbon atoms.
The addition of water to a substance; in organic chemistry, the addition of water across the carbon-to-carbon double bond of an alkene or the carbon-to-oxygen double bond of an aldehyde or ketone
A giant molecule formed by the combination of monomers in a repeating manner
A small molecule that can be combined with other small molecules to make polymers
A reaction in which monomers add to one another to produce a polymeric product that contains all the atoms of the starting monomers.
are hydrocarbons with carbon-to-carbon triple bonds and properties much like those of alkenes
is the simplest member of the alkyne family and its molecular formula is C2H2.
A hydrocarbon with a benzene-like structure.
molecule of benzene has a cyclic, hexagonal, planar structure of six carbon atoms with one hydrogen atom bonded to each.
All the carbon-to-carbon bonds in benzene are equivalent, and the molecule is unusually stable.
Chemists represent benzene as a hexagon with an inscribed circle.
The inner circle indicates that the valence electrons are shared equally by all six carbon atoms.
Any compound that contains a benzene ring or has certain benzene-like properties.
A group derived from an aromatic hydrocarbon by the removal of a hydrogen atom.
The most common aryl group is derived from benzene (C6H6) by removing one hydrogen atom (C6H5) and is called a phenyl group.
Polycyclic aromatic hydrocarbon (PAH)
(End of Ch.13)
An aromatic hydrocarbon consisting of fused benzene rings sharing a common side
(Beginning of Ch.14)
A structural arrangement of atoms and/or bonds that imparts a wide range of important properties to organic compounds
An organic compound with an OH functional group on an aliphatic carbon atom.
Represented by the general formula ROH where R is an alkyl group.
With one to four carbon atoms are frequently called by common names, in which the name of the alkyl group is followed by the word alcohol.
Basic IUPAC rules for naming alcohols:
The longest continuous chain (LCC) of carbon atoms containing the OH group is taken as the parent compound and is numbered from the end nearest the OH group.
The number that indicates the position of the OH group is prefixed to the name of the parent hydrocarbon, and the -e ending of the parent alkane is replaced by the suffix -ol.
If more than one OH group appears in the same molecule (polyhydroxy alcohols), suffixes such as -diol and -triol are used
In these cases, the -e ending of the parent alkane is retained
Physical Properties of alcohols
can be considered derivatives of water and like the H-O-H bond in water, the R-O-H bond is bent, and alcohol molecules are polar.
Alcohols have higher boiling points than do ethers and alkanes of similar molar masses because the OH group allows alcohol molecules to engage in hydrogen bonding.
Alcohols can engage in hydrogen bonding with water molecules.
Hydrocarbons are insoluble in water, alcohols with one to three carbon atoms are completely soluble.
As the length of the chain increases, the solubility of alcohols in water decreases; the molecules become more like hydrocarbons and less like water.
An alcohol with two OH functional groups.
Commonly called glycerol or glycerin, 1,2,3-propanetriol is the most important trihydroxy alcohol.
Glycerol is a product of the hydrolysis of fats and oils
It is a sweet, syrupy liquid.
Are an aromatic compound with an OH group attached directly to a benzene ring.
The parent compound, C6H5OH, is itself called phenol.
It is a white crystalline compound that has a distinctive odor.
Phenols are widely used as antiseptics and as disinfectants.
Are an organic compound that has an oxygen atom between two hydrocarbon groups.
It may be considered a derivative of an alcohol (ROH) in which the hydrogen atom of the OH group is been replaced by a second alkyl or aryl group.
To give ethers common names, name the groups attached to the oxygen atom, followed by the generic name ether.
If both groups are the same, the group name should be preceded by the prefix di.
Ether molecules have no OH group and thus no intermolecular hydrogen bonding.
Ethers have quite low boiling points for a given molar mass.
Ether molecules have an oxygen atom and can engage in hydrogen bonding with water molecules.
An ether molecule has about the same solubility in water as the alcohol that is isomeric with it.
A compound with an carbon-to-oxygen double bond.
define two related families of organic compounds: ketone and aldehyde
An organic compound whose molecules have a carbonyl functional group between two hydrocarbon groups.
An organic compound with a carbonyl functional group that has an hydrogen atom attached and either a hydrocarbon group or a second hydrogen atom
Naming Ketones and Aldehyde
The stem names of aldehydes and ketones are derived from those of the parent alkanes, defined by the longest continuous chain (LCC) of carbon atoms that contains the functional group.
For an aldehyde, drop the -e from the alkane name and add the ending -al.
For a ketone, drop the -e from the alkane name and add the ending -one.
To indicate the position of a substituent on an aldehyde, the carbonyl carbon atom is always considered to be C1; it is unnecessary to designate this group by number.
To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible number.
Properties of Ketones and Aldehydes
Higher aldehydes have pleasant odors and are used in perfumes and artificial flavorings.
Ketones - acetone has a pleasant odor, but most of the higher homologs have rather bland odors.
The oxygen atom of the carbonyl group engages in hydrogen bonding with a water molecule.
The solubility of aldehydes is therefore about the same as that of alcohols and ethers.
Aldehydes are readily oxidized to carboxylic acids, whereas ketones resist oxidation.
Acetone is the simplest and most important ketone.
It is miscible with water and with most organic solvents.
Its chief use is as an industrial solvent.
Thiol (end of Ch.14)
A compound with an SH functional group.
The mild oxidation of thiols gives compounds called disulfides.
Thioethers, which are sulfur analogs of ethers, have the form general formula RSR′
Carboxylic Acid (beginning of Ch.15)
An organic compound that has a carboxyl group
A functional group that contains a carbon-oxygen bond and an OH group also attached to the same carbon atom
An organic compound derived from a carboxylic acid and an alcohol in which the OH of the acid is replaced by an OR group
An organic compound derived from ammonia by the replacement of one, two, or three of the hydrogens atoms by alkyl or aryl groups
An organic compound with a carbonyl group joined to a nitrogen atom from ammonia or an amine
Common carboxylic acids
Formic acid- simplest acid, obtained by the distillation of ants, bites of some ants, and the wings wasps and bees
Acetic Acid-made by fermenting cider and honey in the presence of oxygen; most familiar weak acid used in educational and industrial chemistry laboratories
Benzoic acid- acid with carboxyl group attached directly to a benzene group
Naming carboxylic acids
Parent hydrocarbon is the one that corresponds to the longest continuous chain (LCC) containing the carboxyl group.
The -e ending of the parent alkane is replaced by the suffix -oic and the word acid.
Carboxyl carbon atom is counted first; numbers are used to indicate any substituted carbon atoms in the parent chain
The formation of carboxylic acids
oxidation of aldehydes or primary alcohols from this
Physical properties of carboxylic acids
Colorless liquids with disagreeable odors
Exhibit strong hydrogen bonding between molecules
Chemical properties of carboxylic acids
Water-soluble carboxylic acids ionize slightly in water to form moderately acidic solutions.
Carboxylic acids react with aqueous solutions of sodium hydroxide (NaOH), sodium carbonate (Na2CO3), and sodium bicarbonate (NaHCO3) to form salts.
Carboxylic acid salts are named in the same manner as inorganic salts: the name of the cation is followed by the name of the organic anion.
General formula: RCOR
R may be a hydrogen atom, an alkyl group, or an aryl group.
R′ may be an alkyl group or an aryl group but not a hydrogen atom.
Group name of the alkyl or aryl portion is given first and is followed by the name of the acid portion.
In both the common and IUPAC nomenclature, the -ic ending of the parent acid is replaced by the suffix -ate.
Physical Properties of esters
Ester molecules are polar but have no hydrogen atom attached directly to an oxygen atom.
Absence of the hydrogen atom prevents esters from engaging in intermolecular hydrogen bonding.
Esters are intermediate in boiling points between the nonpolar alkanes and the alcohols, which engage in hydrogen bonding.
Ester molecules can engage in hydrogen bonding with water molecules.
Esters of low molar mass are somewhat soluble in water.
The formation of an ester from a carboxylic acid and an alcohol
The reaction of a substance with water
Ester of Phosphoric Acid
Inorganic acids react with alcohols to form esters.
Inorganic acids such as nitric acid (HNO3), sulfuric acid (H2SO4), and phosphoric acid (H3PO4) form esters.
A phosphoric acid molecule can form a monoalkyl, a dialkyl, or a trialkyl ester by reaction with one, two, or three molecules of an alcohol.
Esters of Phosphoric Acid (2)
Esters of these acids are present in every plant and animal cell.
They are biochemical intermediates in the transformation of food into usable energy.
The bonds between phosphate units in adenosine triphosphate (ATP) are called phosphoanhydride bonds.
Phosphate esters are also important structural constituents of phospholipids and nucleic acids
Water, alcohol, ether
Physical Properties of Amines
The boiling points of tertiary amines, which cannot engage in hydrogen bonding because they have no hydrogen atom on the nitrogen atom, are comparable to those of alkanes and ethers of similar molar mass.
All three classes of amines can engage in hydrogen bonding with water
Amines of low molar mass are quite soluble in water
Amines as Bases
Amines have a lone electron pair on their nitrogen atoms and can accept a proton from water to form substituted ammonium (NH4+) ions and hydroxide (OH−) ions.
Amines will react with strong acids to form salts soluble in water.
Amine salts are named like other salts: the name of the cation is followed by the name of the anion.
A cyclic compound in which one or more atoms in the ring is an element other than a carbon atom
Heterocyclic amines derived from plants
A nitrogen-containing organic compound obtained from plants that has physiological properties
Structure of Amides
The amide functional group has an nitrogen atom attached to a carbonyl carbon atom.
If the two remaining bonds on the nitrogen atom are attached to hydrogen atoms, the compound is a simple amide.
If one or both of the two remaining bonds on the atom are attached to alkyl or aryl groups, the compound is a substituted amide
Amides of five or fewer carbon atoms are soluble in water.
Solutions of amides in water usually are neutral—neither acidic nor basic.
Most amides are solids at room temperature; the boiling points of amides are much higher than those of alcohols of similar molar mass.
Solubility in water results from the polar nature of the amide group and hydrogen bonding
Formation of Amides
Reaction of ammonia (NH3) with a carboxylic acid forms an amide
Water molecules are split out, and a bond is formed between the nitrogen atom and the carbonyl carbon atom
In proteins, the amide functional group is called a peptide bond
The reaction of a diacid and a diamine yields a polyamide.
Some polyamides are known as nylons.
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