1: Nomenclature: Concept Summary

Question 1

Name the 5 steps in the IUPAC Naming System

Answer 1

1) Find the longest carbon chain in the compound that contains the highest-priority functional group. (Parent Chain)
2) Number the chain giving the highest-priority functional group the lowest possible number. This group determines the suffix of the molecule.
3) Name the substituents with a prefix. Multiple substituents of a single type receive another prefix denoting how many are present (di-, tri-, tetra-, etc)
4) Assign a number to each of the substituents depending on the carbon to which it is bonded.
5) Complete the name by alphabetizing the substituents and separating numbers from each other by commas and from words by hyphens.

Question 2

______ are hydrocarbons without any double or triple bonds. They have the general formula CnH(2n+2)

Answer 2

Alkanes

Question 3

____ are named according to the number of carbons present followed by the suffix -ane

Answer 3

Alkanes

Question 4

Name the first 4 alkanes

Answer 4

Methane (CH4), Ethane (C2H6), Propane (C3H8), Butane (C4H10)

Question 5

_____ contains double bonds

Answer 5

Alkenes

Question 6

______ contain triple bonds

Answer 6

Alkynes

Question 7

_____ are named by substituting -ene for the suffix and numbering the double bond by its lower-numbered carbon. _____ substitute -yne with the same numbering.

Answer 7

Alkenes, Alkynes

Question 8

_____ contain a hydroxyl (-OH) group, which substitutes for one or more of the hydrogens in the hydrocarbon chain

Answer 8

Alcohols

Question 9

How are alcohols named?

Answer 9

by substituting the suffix -ol or by using the prefix hydroxy- if a higher priority group is present

Question 10

______ have higher priority than double or triple bonds and alkanes

Answer 10

Alcohols

Question 11

How are the common names of alcohols given?

Answer 11

Common names of alcohols include the name of the carbon chain followed by the word “alcohol”. For example, ethyl alcohol is the same compound as ethanol.

Question 12

____ contain two hydroxyl groups. What are they termed?

Answer 12

Diols; they are termed geminal if on the same carbon or vicinal if on adjacent carbons

Question 13

Aldehydes and ketones contain a ______ -a carbon double-bonded to an oxygen

Answer 13

carbonyl group

Question 14

_____ have the carbonyl group on a terminal carbon that is also attached to a hydrogen atom

Answer 14

Aldehydes

Question 15

How are aldehydes named?

Answer 15

with the suffix “-al” or by using the prefix “oxo-“ if a higher priority group is present

Question 16

List some common names for aldehydes

Answer 16

Methanal: “Formaldehyde”
Ethanal: “Acetylaldehyde”
Propanal: “Propionoaldehyde”

Question 17

_____ have the carbonyl group on a nonterminal carbon

Answer 17

Ketones

Question 18

How are ketones named?

Answer 18

with the suffix “-one” and share the prefix “oxo-“ if a higher priority group is present.
Ketones can also be indicated by the prefix “keto-“

Question 19

How are common names of ketones given?

Answer 19

The common names of ketones are constructed nu naming the alkyl groups on either side alphabetically and adding ketone. For example, 2-butanone is called “ethylmethylketone”

Question 20

What is the smallest ketone? What is its designated IUPAC name?

Answer 20

Acetone

IUPAC name: Propanone

Question 21

What are carbonyl containing compounds?

Answer 21

Aldehydes
Ketones
Carboxylic Acids + Derivatives

Question 22

How are the carbons designated for carbonyl containing compounds?

Answer 22

there is a lettering scheme for carbons. The carbon adjacent to the carbonyl carbon is the alpha-carbon.

Question 23

_______ are the highest-priority functional group because they contain 3 bonds to oxygen: one from a hydroxyl group and 2 from a carbonyl group.

Answer 23

Carboxylic Acids

Question 24

______ are ALWAYS terminal, although their derivatives may occur within a molecule

Answer 24

Carboxylic Acids

Question 25

How are carboxylic acids named?

Answer 25

with suffix “-oic acid”

They are very rarely named as a prefix

Question 26

How the common names for carboxylic acids derived?

Answer 26

Common names for carboxylic acids follow the trend for aldehydes. Formic acid is methanoic acid, acetic acid is ethanoic acid, and propionic acid is proanoic acid.

Question 27

___ are carboxylic acid derivatives where “-OH” is replaced with “-OR”, an alkoxy group

Answer 27

Esters

Question 28

How are esters named?

Answer 28

with the suffix “-oate” or the prefix “alkoxycarbonyl-“

Question 29

How are the common names for esters derived?

Answer 29

Common names for esters are derived from the alcohol and the carboxylic acid used during synthesis

Question 30

____ replace the hydroxyl group of a carboxylic acid with an amino group that may or may not be substituted

Answer 30

Amides

Question 31

How are amides named?

Answer 31

with the suffix “-amide” or the prefixes “carbamoyl-“ or “Amido-“
Substitutents attached to the amide nitrogen are designated with a capital “N-“

Question 32

______ are formed from two carboxylic acids by dehydration. They may be symmetric (two of the same acid), asymmetric (two different acids) or cyclic (intramolecular reaction of a dicarboxylic acid)

Answer 32

Anhydrides

Question 33

How are anhydrides named?

Answer 33

named using the suffix “-anhydride” in place of an acid
If the anhydride is formed from more than one carboxylic acid, both are named in alphabetical order in the name before the word “anhydride”

Question 34

Functional groups are arranged in order of priority as follows:
__1___ > ___2___ > ___3___> ___4___>__5___>___6___>___7___>___8___>___9___ or ___10___

Answer 34

Carboxylic acids > Anhydride > Ester > Amide > Aldehyde > Ketone > Alcohol > Alkene or Alkyne > Alkane