Organic Chemistry

Question 1

First step of IUPAC naming

Answer 1

Identify the longest carbon chain containing the highest-order functional group
Parent chain used to determine root of the name
More substituted chain gets priority as the parent chain

Question 2

Highest-priority functional groups

Answer 2

Most oxidized carbon

Provide the suffix for the name

Question 3

Second step of IUPAC naming

Answer 3

Number the chain
Carbon #1 is closest to the highest-priority functional group
OR substituted carbons should be numbered as low as possible

Question 4

Oxidation state increases with…

Answer 4

More bonds to heteroatoms

O, N, P, or halogens

Question 5

Oxidation state decreases with…

Answer 5

More bonds to hydrogen

Question 6

Priority of double and triple bonds

Answer 6

Double bonds take precedence if there is a tie between assigning priority in a molecule with both

Question 7

Third step of IUPAC naming

Answer 7

Name the substituents
Substituent’s name is placed at the beginning of the compound name as a prefix, followed by the name of the longest chain
Suffix: -yl
Prefixes: di-, tri-, tetra- to describe how many of the same substituents there are

Question 8

Fourth step of IUPAC naming

Answer 8

Assign a number to each substituent

Pair the named substituents to the corresponding number on the parent chain

Question 9

Fifth step of IUPAC naming

Answer 9

Complete the name
Names begin with the names of the substituents in alphabetical order
Each substituent is preceded by its number on the parent chain
Numbers are separated from each other with commas and from words with hyphens
The name of the backbone chain and the suffix for the highest-priority functional group are at the end
EX: 4-ethyl-5-isopropyl-3,3-dimethylocatane

Question 10

Hydrocarbons

Answer 10

Compounds that contain only carbon and hydrogen atoms

Question 11

Alcohols

Answer 11

Compounds that contain at least one -OH group which lends them additional reactivity
Suffix: -ol
Usually takes precedence as highest-priority functional group
If it is not highest-priority it is named as the hydroxyl substituent hydroxy-

Question 12

Alkanes

Answer 12

Simple hydrocarbons with formula CnH(2n+2)
Suffix: -ane
Prefixes from 5-12 C: pent-, hex-, hept-, oct-, non-, dec-, undec-, and dodec-

Question 13

Methane

Answer 13

One carbon alkane

Question 14

Ethane

Answer 14

Two carbon alkane

Question 15

Propane

Answer 15

Three carbon alkane

Question 16

Butane

Answer 16

Four carbon alkane

Question 17

Alkyl halides

Answer 17

Halogen substituents on alkanes

Prefixes: fluoro-, chloro-, bromo-, or iodo-

Question 18

Alkenes

Answer 18

Double bonds

Suffix: -ene

Question 19

Alkynes

Answer 19

Triple bonds

Suffix: -yne

Question 20

Diols/glycols

Answer 20

Alcohols with two hydroxyl groups
Suffix: -diol
Hydrocarbon name is persevered and -diol is added

Question 21

Germinal diols/hydrates

Answer 21

Diols with hydroxyl groups on the same carbon

Not common because they spontaneously dehydrate to produce carbonyl compounds with C=O functional groups

Question 22

Vicinal diols

Answer 22

Diols with hydroxyl groups on adjacent carbons

Question 23

Carbonyl

Answer 23

C=O

Question 24

Aldehydes

Answer 24

Contain a carbonyl
Appear at the end of a parent chain
Suffix: -al
Substituent prefix: oxo-
Usually takes precedence over many other groups

Question 25

Ketones

Answer 25

``` Contain a carbonyl Found in the middle of a carbon chain Suffix: -one Substituent prefixes: oxo- or keto- Named by listing alkyl groups in alphabetical order, followed by “ketone” ```

Question 26

Common name for methanal

Answer 26

Formaldehyde

Question 27

Common name for ethanal

Answer 27

Acetaldehyde

Question 28

Common name for propanal

Answer 28

Propionaldehyde

Question 29

Common name for propanone

Answer 29

Acetone

Question 30

Carboxylic acid

Answer 30

Contains a carbonyl group and hydroxyl group on a terminal carbon Highest-priority functional group on MCAT Suffix: -oic acid

Question 31

Common name for methanoic acid

Answer 31

Formic acid

Question 32

Common name for ethanoic acid

Answer 32

Acetic acid

Question 33

Common name for propanoic acid

Answer 33

Propionic acid

Question 34

Esters

Answer 34

Carboxylic acid derivative Hydroxyl group (-OH) is replaced with an alkoxy group (-OR, where R is a hydrocarbon chain) First term is the alkyl name of the esterifying group Second term is the name of the parent acid with “-oate” replacing “-oic acid”

Question 35

Amides

Answer 35

Carboxylic acid derivative Hydroxyl group (-OH) is replaced with amino group (contains N) Suffix: -amide Substituents attached to the nitrogen are labeled with “N-“, are included as prefixes, and are not numbered

Question 36

Anhydrides

Answer 36

Carboxylic acid derivative Named by replacing “acid” with “anhydride” if it is formed from one type of a carboxylic acid If it is not symmetrical, both carboxylic acids are named without the “acid” suffix and then “anhydride” is added

Question 37

What would be the names of the ester, amide, and anhydride derivatives of pentatonic acid? Assume that the R group on the ester is -CH3 and that the amide is unsubstituted.

Answer 37

Ester: methyl pentanoate Amide: pentanamide Anhydride: pentanoic anhydride

Question 38

Order of functional group priority

Answer 38

Carboxylic acid > anhydride > ester > amide > aldehyde > ketone > alcohol > alkene or alkyne > alkane Alkenes have higher priority than alkynes in cyclic compounds