PRELIM 03 - Nomenclature, Structure, and Stereochemistry Flashcards
Compounds with the same molecular formula
Isomers
Different connectivity of atoms
Constitutional
Different functional groups
Functional
Different positions of functional group
Positional
Different carbon skeleton
Skeletal
Same connectivity but different spatial orientation of atoms
Stereoisomers
Different, non-interconverting spatial arrangement of atoms
Configurational
Result from restricted rotation around a double bond or on cyclic alkanes
Geometric
Around a chiral carbon
Optical
Non-superimposable mirror images
Enantiomers
Non-mirror images
Diastereomers
Different, interconverting spatial arrangement of atoms, the result of rotation about single bonds; same compound
Conformational
Usually uses the name given when it was discovered
Common name
Names compound as a derivative of a parent compound
Derived name
Most systematic; based on the longest continuous chain of carbon atoms
IUAPC (International Union of Pure and Applied Chemistry) Name
Where and what are the substituents?
Prefix
How many carbons?
Parent
Where is the primary functional group?
Locant
What is the primary functional group?
Suffix
Number of carbon atoms: 11
Undec-
Number of carbon atoms: 12
Dodec-
Number of carbon atoms: 13
Tridec-
Number of carbon atoms: 14
Tetradec-
Number of carbon atoms: 15
Pentadec-
Number of carbon atoms: 16
Hexadec-
Number of carbon atoms: 17
Heptadec-
Number of carbon atoms: 18
Octadec-
Number of carbon atoms: 19
Nonadec-
Number of carbon atoms: 20-
Eicos-
Compounds that contain carbon and hydrogen only
Hydrocarbons
Open chain (acyclic); can either be a straight chain or branched
Aliphatic
Has a closed ring but no aromaticity
Alicyclic
Has a benzene ring
Aromatic
Contains C-C bonds
Saturated
Contains at least one C=C or C≡C bond
Unsaturated
Other name for alkanes
Paraffins
Paraffin is derived from __________, meaning “slight affinity”
L. parum affinis
Found in the waxy coating on cabbage leaves
Nonacosane
Found in wood oil of the Jeffrey pine common to the Sierra Nevada mountains of California
Heptane
Consists chiefly of methane but also contains ethane, propane, and butane
Natural gas
A complex mixture of hydrocarbons that must first be separated into various fractions and then further refined before it can be used
Petroleum
Prefix of carboxylic acid
Carboxy
Prefix of ester
Alkoxycarbonyl
Prefix of amide
Amido
Prefix of nitrile
Cyano
Prefix of aldehyde (=O)
Oxo
Prefix of aldehyde (CH=O)
Formyl
Prefix of ketone (=O)
Oxo
Prefix of alcohol
Hydroxy
Prefix of amine
Amino
Prefix of alkene
Alkenyl
Prefix of alkyne
Alkynyl
Prefix of alkane
Alkyl
Prefix of ether
Alkoxy
Prefix of alkyl halide
Halo
Prefix used for unbranched chains
n (normal)
Prefix used for a methyl group attached to the 2nd C
Iso
Prefix used for 4 methyl groups attached to one C
Neo
Other name for alkenes
Olefins
A plant hormones that induces ripening in fruit
Ethylene
The major component of turpentine
α-pinene
a polyalkene that contains 11 double bonds; the orange pigment responsible for the color of carrots
β-carotene
Alkene separated by at least 2 single bonds
Isolated
Adjacent alkenes
Cumulative
Alkenes that are alternating with single bonds
Conjugated
System used for disubstituted alkenes
Cis-Trans system
System used for tri- and tetrasubstituted alkenes
E/Z system
From the German word ‘entgegen’, meaning opposite; specifies that groups of higher priority on the carbons of a double bond are on opposite sides
E
German word which means opposite
Entgegen
From the German word ‘zusammen’, meaning together; specifies that groups of higher priority on the carbons of a double bond are on the same sides
Z
German word which means together
Zusammen
Were used to describe fragrant substances; now used to describe cyclic organic compounds with high degree of unsaturation
Aromatic compounds
From coal distillate
Benzene
From cherries, peaches, and almonds
Benzaldehyde
From tolu balsam
Toluene
An aromatic hydrocarbon that has 2, 6, 10, 14, 18 or so forth pi electrons satisfies __________
Huckle’s criteria for aromaticity
A fuel additive, an industrial solvent, and a beverage
Ethanol
A general disinfectant, commonly called carbolic acid
Phenol
The familiar ‘ether’ of medical use; frequently used as a reaction solvent
Diethyl ether
A characteristic stench made from a thiol
Skunk scent
Is a key part of numerous biological processes
Thiol-disulfide interconversion
Responsible for fish-like aroma
Trimethylamine
An aldehyde that is a coenzyme involved in a large number of metabolic reactions
Pyridoxal phosphate (PLP)
A steroid hormone w/ ketone group; secreted by the adrenal glands
Cortisol/Hydrocortisone
Produced for use in building insulation materials and in the adhesive resins that bind particle board and plywood
Formaldehyde
Widely used as an industrial solvent
Acetone
The principal organic component of vinegar
Acetic acid
Responsible for the rancid odor of sour butter
Butanoic acid
Responsible for the aroma of goats and dirty socks
Hexanoic acid/Caproic acid
Found in pineapple oil
Methyl butanoate
Found in banana oil
Isopentyl acetate
A commonly used solvent; plastic balloon odor
Ethyl acetate
Used as plasticizers to keep polymers from becoming brittle
Dialkyl phthalates
Cyclic ethers with a three-membered ring
Epoxides
Sulfur analog of esters
Thioesters/Sulfides
Derivatives of ammonia in which one or more hydrogens are replaced by alkyl or aryl groups
Amines
Cyclic esters
Lactone
Has two acyl groups bonded to an oxygen atom
Acid anhydrides
Has no carbonyl group but is treated as carboxylic acid derivatives
Nitriles
