Chapter 1: Nomenclature Flashcards
What is Step 1 of IUPAC naming?
Identify the longest carbon chain with the highest-order functional group
This longest carbon chain will be known as the parent chain
If there are 2+ chains of equal length, which chain gets higher priority?
The more substituted chain.
What is Step 2 of IUPAC naming?
Number the chain
The carbon marked as #1 is the one closest to the high-priority functional group
If all functional groups have the same priority, the most substituted carbons should get the lowest numbers
What is Step 3 of IUPAC naming?
Name the substituents
Functional groups that are NOT part of the parent chain
What is the suffix for carbon chain substituents?
“-yl”
Draw
t-butyl
common alkyl substituent
Draw
isopropyl
common alkyl substituent
Draw
isobutyl
common alkyl substituent
Draw
sec-butyl
common alkyl substituent
What is Step 4 of IUPAC naming?
Assign a number to each substituent
Pair substituents that you have named to the corresponding numbers in the parent chain.
Substituents also get a carbon # designation.
Use di-, tri-, tetra-, etc. to indicate multiple substituents of the same type
What is Step 5 of IUPAC naming?
Complete the name
Names of substituents are listed in alphabetical order, with each substituent preceded by its number
Prefixes are ignored while alphabetizing, with the acception of nonhyphenated roots like iso-, neo-, cyclo-, etc.
Heteroatom
Atoms besides carbon and hydrogen, e.g. oxygen, nitrogen, phosphorus, or halogens
What does it mean to be in a “lower oxidation state”?
Lots of carbon-hydrogen bonds = lower oxidation state, or a more reduced state
What does it mean to be in a higher oxidation state?
If it contains a lot of carbon-heteroatom bonds
Alkanes
Simple hydrocarbon molecuels with the formula CnH2n+2
What are common substituents on alkanes?
Halogens, e.g. fluoro-, chloro-, bromo-, iodo-
Alkenes and alkynes
Alkene = double bond
Alkyne = triple bond
named like substituents
not usually tested on MCAT except for unsaturated fatty acids
Which substituent gets the lowest numbered carbon?
The highest priority substituent
What is the suffix and functional group called?
Alcohol
suffix “-ol”
-OH = hydroxyl group
Which takes priority, alcohol or multiple bonds?
Alcohol, because they are more oxidized.
How do you denote an alcohol if it is the highest priority?
“-ol”
How do you denote an alcohol if it is NOT the highest priority?
“hydroxy-“
Diols
aka “glycol”
Alcohol with 2 hydroxyl groups
Geminal diols
2 alcohols on the SAME carbon, aka hydrates
Not very common because they spontaneously dehydrate to produce carbonyl compounds
Vicinal Diols
2 alcohols on ADJACENT carbons
What type of group do aldehydes and ketones contain?
C
A carbonyl group (C=O)
What is the difference between aldehydes and ketones?
Aldehydes are chain-terminating; ketones are in the middle of the carbon chain
What is the suffix and functional group called? Draw.
Aldehydes
Suffix “-al” if at position 1 (which it usually is, so you don’t need to number)
Draw methanal
Common name?
common aldehyde
formaldehyde
formal = 1 carbon
acetaldehyde
ethanal
common aldehyde
acet = 2 carbons
propionaldehyde
propanal
common aldehyde
propion = 3 carbons
What is the suffix and functional group called? Draw.
Ketones
suffix “-one”
Always have to assign a # to these, since they are always in the middle of a carbone chain
What do you call ketones when there is a higher priority group than a carbonyl present in the molecule?
Use the prefix “oxo-“
How do you name carbons relative to the carbonyl?
The carbon adjacent to the carbonyl is the “alpha” carbon
What is the suffix and functional group called? Draw.
Carboxylic Acids
carbonyl (C=O) + hydroxyl (-OH) on terminal carbon
What is more oxidized than a carboxylic acid?
CO2, since it has 4 bonds to oxygen
Draw
methanoic acid
Common name?
common carboxylic acid
formic acid
formal = 1 carbon
Draw
ethanoic acid
Common name?
common carboxylic acid
acetic acid
acet = 2 carbons
Draw
propanoic acid
propionic acid
common carboxylic acid
propion = 3 carbons
How do you name? What is the functional group called? Draw.
Esters
Suffix = “-oate”
hydroxyl (-OH) is replaced with alkoxy (-OR) group
1st term = alkyl name of esterifying group
2nd term = parent acid
What is the suffix? What is the functional group called? Draw.
Amide
hydroxyl replaced by amino, the N can be bonded to 0, 1, or 2 alkyl groups
Suffix “-amide”
Substituents attached to the N are labeled with the prefix “N-“
How do you name? What is the functional group called? Draw.
Anhydride
Forms from 2 carboxylic acid molecules, removes 1 H2O
Many are cyclic – > formed from intramolecular dehydration
“________ anhydride”
Order by priority, from highest to lowest
ketone
alkene
anhydride
carboxylic acid
ester
alkane
amide
alkene
alcohol
aldehyde
carboxylic acid
anhydride
ester
amide
aldehyde
ketone
alcohol
alkene = alkyne
alkane
What is the prefix and suffix for this functional group?
carboxylic acid
Prefix: carboxyl-
Suffix: -oic acid
What is the prefix and suffix for this functional group?
anhydride
Prefix: alkanoyloxycarbonyl-
Suffix: anhydride
What is the prefix and suffix for this functional group?
ester
Prefix: alkoxycarbonyl-
Suffix: -oate
What is the prefix and suffix for this functional group?
amide
Prefix: carbamoyl- or amido-
Suffix: -amide
What is the prefix and suffix for this functional group?
aldehyde
Prefix: oxo-
Suffix: -al
What is the prefix and suffix for this functional group?
ketone
Prefix: oxo- or keto-
Suffix: -one
What is the prefix and suffix for this functional group?
alcohol
Prefix: hydroxyl-
Suffix: -ol
What is the prefix and suffix for this functional group?
alkene
Prefix: alkenyl-
Suffix: -ene
What is the prefix and suffix for this functional group?
alkyne
Prefix: alkynl-
Suffix: -yne
What is the prefix and suffix for this functional group?
alkane
Prefix: alkyl-
Suffix: -ane
