Properties of Organic Compounds
- covalent bonds
- low melting and boiling points
- flammable and undergo combustion
- not soluble in water
Constitutional isomers
- compounds with same molecular formula but different structural formulas
- Structural formulas give more info than molecular formula
- # of isomers increases with # of carbons
Stereoisomers
- 3-dimensional shape of a molecule
- Conformations are shapes that a molecule
- can take because of bond rotations
Properties of Carbon
- Small size enables close approach
- Strong bonds to itself and other elements
- Can have long chains, cyclic arrangements or both
Hydrocarbons
Name
Definition
Hydrocarbon
hydrogen + carbon
Hydrocarbon derivative
carbon and hydrogen +
O, N, S, P, F, Cl, Br
Alkanes
Single bonds
tetrahedral 109.5°
Alkenes
Double bond
Naming
1. Find longest continuous chain of carbon atoms
and number from end nearest to first alkyl group
2. Identify alkyl groups and where they are
attached
3. Use prefixes di, tri, tetra, etc. when have two
4. or more identical substituents
5. Alphabetize alkyl groups and specify position
6. Iso and cyclo prefixes considered in the
alphabetizing.
7. End with the name of the parent chain
+ “ane”
+
“ene”
+
“yne”
trigonal planar 120°
Alkynes
Triple bond
linear 180°
Cycloalkane
One or more carbon rings
with single C-C bonds
+
“Cyclo” at the beginning
Number substituents with lowest number alphabetical
order
Cycloalkene
One or more carbon rings
with double C-C bonds
Aromatic hydrocarbon/ring
Cyclic ring with alternating
single and double bonds
1. “benzene” as parent ring
2. If one substituent, location not indicated
3. If multiple substituents, ring is numbered to give
the lowest possible numbers
• ortho (o) - 1,2 relationship
• meta (m) - 1,3-relationship
• para (p) - 1,4-relationship
(benzene)
Alcohols
Name
Definition
Naming
Alcohols
-OH attached to alkane
Number from end nearest -OH
Replace “e” with “ol”
Specify OH location for carbon chains longer than 2
Identify alkyl groups as usual
R-OH
Classified according to the # of carbons attached to the
carbon directly attached to the -OH
Phenols
-OH and aromatic ring
The carbon bearing the OH in the phenol is always C-1
Ethers
Name
Definition
Naming
Ethers
Carbon - oxygen - carbon
Name the groups attached to the O as alkyl groups and
add “ether,” using prefix based on number of repeat
groups as applicable (example to the left is dimethyl
ether)
Name
Definition
Naming
Thiols
Contain an –SH attached
to alkane
Number from end nearest -SH
Alkane name + “thiol” (example to left is ethanethiol)
Specify SH location for carbon chains longer than 2
Identify alkyl groups as usual
Name
Definition
Naming
Aldehydes
carbonyl (C=O)
attached to one H and
either a second H or a C
The parent chain must include the carbonyl group
Parent numbered from end nearest the carbonyl
C-O-C
Thiols
RSH
Aldehydes
Aldehyde carbonyls are always C-1 and not indicated
in the name
Aldehyde: drop “e” and add “al”
Ketones
Name
Definition
Naming
Ketones
carbonyl (C=O) attached to
two other Cs
The parent chain must include the carbonyl group
Parent numbered from end nearest the carbonyl
Ketone: drop “e” and add “one”
Carboxylic Acids
Name
Definition
Naming
Carboxylic acids
Carboxyl
-OH attached to a caronyl
(C=O)
Parent chain is longest continuous carbon chain
that includes the carboxyl group
• Numbering begins at the carboxyl group
• Alkyl groups are identified by name, position and
number of appearances
• For IUPAC names, drop “e” on the name of the
corresponding hydrocarbon and add “oic acid”
Carboxylic acid salts
Carboxylate ion
Replace “ic acid” with “ate”
Esters
Name
Definition
Naming
Esters
C-O-C
One of the carbons is a
carbonyl
Esters are named in two parts
• First: the alkyl group in the alcohol residue
• Second: change the ending on the name of the
carboxylic acid residue from “ic acid” to “ate”
Name
Definition
Naming
Amines
Classified by the number of
carbon atoms directly
attached to the N
• primary (1°): 1 C
secondary (2°): 2 C
• tertiary (3°): 3 C
• quaternary (4°): 4 C
N atom carries a +1 formal
charge
The parent chain of amines is the longest chain of
carbon atoms attached to the amine.
• Named as alkylamines
• List the names of the alkyl groups bonded to the N
atom in
alphabetical order in front of the word amine
• Use prefixes to identify duplicate alkyl substituents
Amines
Aromatic amines
Amine of benzene is aniline
Alkyl groups on the N use the prefix N- with the alkyl
name
Amides
Name
Definition
Amides
General structure:
Naming
Amide names are based on the parent carboxylic acid:
A nitrogen group (-NH2)
replaces the
hydroxyl/alcohol (-OH)
group on carboxylic acids
• For simple amides containing an -NH2, change “oic
acid” to “amide”:
Propanamide
Stars are either H or C
groups.
• When amine residue is present, substituents attached
to the nitrogen are identified and “N” is used to identify
location
N-ethyl-3,3-dimethylbutanamide