Nomenclature Flashcards
IUPAC Naming Steps
1) Identify longest carbon chain containing the highest order functional group
2) Number the chain
3) Name the substituents
4) Assign a Number to each Substituent
5) Complete the name
IUPAC: Identify Longest Carbon Chain containing Highest Order Fxnal Group
this is parent chain, determines the root of name
highest priority fxnal group provides the suffix
more substituted chain gains priority as the parent chain
IUPAC: Number the chain
carbon numbered 1 will be that closest to the highest-priority functional group!!
***rings are also numbered starting from point of highest substitution
The more oxidized a carbon…
the higher its priority!
Oxidation state increases with more bonds to _ and decreases with more bonds to __
heteroatoms , hydrogen
When concerning double and triple bonds for priority…
double bonds have higher priority
Naming Carbon Chain Substituents
the suffix -ane is shifted to -yl
ex: methyl, ethyl, n-propyl
Common Alkyl Substituents
t-butyl, neopentyl, isopropyl, sec-butyl, isobutyl
When there are multiple substituents of the same type,…
use the prefixes di-,tri-, tetra- before the substituents name
Completing the name…
start with substituents in alphabetical order with their carbon numbers coming before the name
**PREFIXES LIKE DI, TRI ARE IGNORED
**HOWEVER ISO, NEO, CYCLO are included!!!
then end with name of backbone chain with the suffix of highest priority functional group
ex: 4-ethyl-3,3-dimethyloctane
Alkanes
simple hydrocarbons with the formula: C(n)H(2n+2)
prefix: alkyl-
suffix: -ane
methane, ethane, propane, butane, pentane, hexane, heptane, octane
Alkyl Halides
just add: fluoro, chloro, bromo, iodo as prefix before the alkane name
ex: fluorohexane
Alkenes and Alkynes
double and single bonded carbon chains respectively
prefix: alkenyl and alkynyl respectively
end with the suffix: -ene and -yne respectively
number for the substituent can be a prefix or in the middle
Alcohols
replace the -e with -ol
prefix: hydroxy
ethane -> ethanol
ex: 5-methyl-2-heptanol
carbon attached to the oxygen of alcohol is given the lowest carbon number as that carbon is the most oxidized
***if it is not the highest, priority group, then it is hydroxy- prefix
Common name Alcohol
alkyl group + alcohol
ethyl alcohol and isopropyl alcohol ; as opposed to ethanol and 2-propanol
Diols/Glycols
alcohols with two hydroxyl groups ; the alcohol groups must be numbered and the suffix for the main carbon chain will be -diol
Geminal Diol/ Hydrates
Diols with two hydroxyl groups on name carbon
not often seen because they spontaneously dehydrate turning into a carbonyl
Vicinal Diol
Diols with two hydroxyl groups on adjacent carbons
Aldehydes
contain carbonyl, chain terminating (appear at end of chain)
often take precedence, suffix foes from -e to -al
butanal
Ketones
contain carbonyl, appear in the middle of chain
-e is replaced with suffix -one
Commonly named by listing all the alkyl groups in alphabetical order and then ending with ketone such as: ethylmethylketone
Common names of methanal, propanal, ethanal
formaldehyde, propionaldehyde, and acetalaldehyde respectively
Smallest possible ketone
Acetone (2 carbons)
When higher priority groups are around than aldehydes and ketones…
prefix oxo- is used, sometimes keto- for ketones
Alpha, Beta, Gamma and Delta Carbons
A - Carbon adjacent to carbonyl carbon
B - Carbon adjacent to A
G - Carbon adjacent to B
D - Carbon adjacent to G
Carboxylic Acid
contain carbonyl group and hydroxyl group on a terminal carbon
It is the MOST oxidized functional group so always prioritized first
prefix: carboxy-
suffix: -e goes to -oic acid
ex: methanoic acid, ethanoic acid, propanoic acid
Common names for:
methanoic Acid
ethanoic acid
propanoic acid
formic acid, acteic acid, propionic acid
Esters
carboxylic acid with an -OR instead of -OH
prefx: alkoxcarbonyl-
2 parts in naming:
1) bonded to O: alkyl name
2) bonded to carbonyl carbon: -oic acid suffix is replaced with -oate
ex: ethyl propanoate
Amides
hydroxyl group is replaced with a amino group attached to the carbonyl carbon
Prefix: amido/carbmoyl
named similarly like esters but -oate is changed to amide and substituents bound to the nitrogen are labeled with N- prefix
ex: N-ethyl-N-methylbutanamide
Anhydrides
occur when two carboxylic molecules are dehydrated
many are cyclic
prefix: alkanoyloxycarbonyl
suffix: acid is replaced with anhydride
if unsymetric, both carboxylic acids are named before anhydride is added
ethanoic propanoic anhydrie
Order of priority
Carboxylic Anhydride Ester Amide Aldehyde Ketone Alcohol Alkene~Alkyne Alkane
