10 organic nomenclature notes
TRANSCRIPT
Organic Nomenclature
Naming Carbon Based Molecules
Organic Nomenclature Tutorial
Organic Nomenclature Quizzes
Summary Chart of Organic Structures
Basics of naming an organic cmpd:
• Find the longest continuous carbon chain– This is the parent chain– Use a root prefix to indicate # of C’s
• Ex: meth, eth, prop, etc.
• Number the C’s from the end nearest the side groups– Side grps should be on lowest combination of C’s
• Name the side groups (alphabetical order if >1)• Number the side groups
– # corresponds to the C the side group is attached to
Root Prefixes for Organic Cmpds.Meth = 1 Oct = 8
Eth = 2 Non = 9
Prop = 3 Dec = 10
But = 4
Pent = 5
Hex = 6
Hept = 7
I. Saturated Hydrocarbon
1. Straight Chain HCa) n – root + ane
b)
c) Try this: CH3CH2
CH2
CH2
CH3
CH3CH2
CH2
CH3
2. Branched Chain HCa) # + side group + root + ane
b) Branch = if derived from alkane drop –ane and add –yl
n-pentane
n-butane
Alkyl Side Groups
Isopropyl-CH3 C CH3
H
Sec-butyl-
CH3 C CH3
CH3 Tert-butyl-(AKA: t-butyl)
Phenyl-
Methyl-
C
H
C
H
H
HH
Ethyl-
C
H
C
H
H
HH
C
H
H
Propyl-
C
H
H
H
CH3CH
CH3CH3
I. Saturated Hydrocarbon2. Branched Chain (cont’d)
c) Use di, tri, tetra, etc. to describe multiple side groups of the same kind (ex. triethyl-)
d) Arrange names of side groups in alphabetical order
2,2-dimethylbutane 2, 2, 3-trimethylpentane
CH3 C CH2
CH3CH3
CH3
CH3 C H2C
CH3CH3
CH3 CH2 CH3
Structural Isomers… • Same molecular formulas but different
arrangements of atoms (different structural formulas)
– Ex. butane and methyl propane are isomers
II. Unsaturated HC 1. Naming Alkenes – double bonds
a) # + side group + # + root + ene
b) Number chain so double bond gets lowest #
Try this:
Side groups: Root Chain: Location of bond:Family:
4-methyl-2-pentene
CH3
CH2CH3
CH3
4-methylPent-
2nd carbon-ene
Hint: # the C’s so the double bond gets lowest value
II. Unsaturated HC2. Naming Alkynes – triple bonds
a) # + side group + # + root + yne
b) Number chain so triple bond gets lowest #
Try this:
Side groups: Root Prefix: Location of bond:Family:
6-methylHept-
3-yne
6-methyl-3-heptyneCH3 H2C
CH2 C C
CH3
CH2
CH3
III. Cyclic Molecules *
• # + side group + Cyclo + root + family suffix– If side groups, number ring so side group gets
lowest #– If double bond, number it to get lowest #
• Try this:
Side groups: Root Chain: Family:
1-ethyl-2-methylCyclopent-
-ane
1-ethyl-2-methylcyclopentane
H2C
CH
CH2CH2
H2CCH3
CH3
Remember: These are listed alphabetically
Other Stuff
Substituent Name
-Br Bromo-
-F Fluro-
-Cl Chloro-
-I Iodo-
-NO2 Nitro-
-OH Hydroxy-(used if not
alcohol)
Other things that could be attached to chain:
Cis- and Trans-
cis-2-butene trans-2-butene
Name These:
Cis-3-hexenetrans-3-hexene
IV. Alcohols (R-OH) *1. # + side group + root + # + ol
2. -OH should get lowest number
3. See rules from I-III for additional info. Try This:
H2C
CH
CH2CH2
H2CCH3
OH
Side groups: Root Chain: Location of -OH:Family:
Cyclopentan-1
-ol
2-ethylcyclopentanol
2-ethyl
Can omit the 1 in the name. It is assumed to be on C #1 if no # listed.
IV. Alcohols (R-OH)Alternative Names:
2-ethylcyclopentanol
2-ethyl-1-cyclopentanol
2-ethylcyclopentan-1-ol
Draw: 2-ethyl-3-cyclopenten-1-ol
V. Aldehydes * -CHO 1. Root = longest C chain that contains
aldehyde group
2. Number C’s beginning at aldehyde group (this is always son C #1)
3. Aldehyde group requires no # in name
4. Root = ends in –al Ex. ethanal
5. Name side group according to previous rules
V. Aldehydes (examples)
Side groups: Root Chain: Family:
2-bromo-Hexan-
-al
2-bromohexanal
Side groups: Root Chain: Family:
3-hydroxy, 2-ethylButan-
-al
2-ethyl-3-hydroxybutanal
VI. Ketones * 1. Number C’s so keto group gets
lowest #2. Root = longest C chain w/keto group
on it3. Use # to indicate location of keto
group4. Root ending = -one5. Ex. propanone
VI. Ketones (examples)
Side groups: Root Chain: Location of Keto:Family:
3-methyl, 5-methylHeptan-
4-one
3, 5-dimethyl-4-heptanone
Side groups: Root Chain: Location of double bond:Location of Keto:Family:
N/Apenten-
3
-one2
Pent-3-en-2-one
VII. Carboxylic Acids* -COOH
1. Carboxy group always on C #1
2. Root = longest C chain w/carboxy group on end
3. Suffix = -oic acid
4. Ex. Ethanoic acid
VII. Carboxylic Acid (examples)Side groups: Root Chain: Location of double bond:Family:
N/AHexen-
2-oic acid
Cis-2-Hexenoic acid
Side groups: Root Prefix: Family:
N/AHexan-
-dioic acid
Hexanedioic acid
VIII. Ethers* R-O-R’1. General form of Name: alkyl alkyl ether
2. Examples:
side chain #1 Side chain #2
Dimethyl ether
Methyl propyl ether
Methyl isopropyl ether
IX. Esters* R-COO-R’ • Formed from dehydration rxn between alcohol
and carboxylic acid
(alcohol – ol + yl) (carboxylic acid –oic acid + oate)
• Example:
R1 R2 R1 R2C
O
+
O
COH OH +O H2O
carboxylic acid
alcoholester
methyl ethanoate
IX. Esters (examples)
Alcohol:Carboxylic Acid:
cyclohexanolethanoic acid
cyclohexylethanoate
2-heptanolAlcohol:Carboxylic Acid: butanoic acid
2-heptanylbutanoate
Alcohol acid
Alcohol acid
--yl--------ate
--yl--------ate
X. Amines * 1. Name each R group but change to –yl
ending (i.e. if R1 is CH3 group = methyl)
2. Name all side groups in alphabetical order
3. Followed by word “amine”• Ex. Ethyl methyl amine
4. If more than one side group is same, use di, tri, etc. to indicate how many
• Ex. diethyl amine
R1 N R2
R3
X. Amine (examples)R1:R2:R3:
cyclopentyl Cyclopentyl amine
ethylethyl Diethyl amine
methylethyl
Diethyl methyl amine
R1:R2:R3:
R1:R2:R3: ethyl