Functional Groups - PowerPoint Presentation

Slide1

Functional GroupsSlide2

Functional GroupsFunctional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity.Slide3

Organic halides: a hydrogen is replaced by a halogenfluoro-,

chloro

-,

bromo

-, iodo-2-iodobutaneSlide4

Organic halides: a hydrogen is replaced by a halogenfluoro-, chloro-, bromo-, iodo-

2,4-dibromo-1-hexeneSlide5

Organic halides: a hydrogen is replaced by a halogenfluoro-, chloro-, bromo-, iodo-

1-bromo-2-chlorobenzeneSlide6

Alcohols & phenols: contain the hydroxyl group (-OH)

alcohols:

at least 1 H on a hydrocarbon is replaced by OH

phenols:

at least 1 H on an aromatic ring is replaced by OH2-propanolSlide7

Alcohols & phenols: contain the hydroxyl group (-OH)alcohols: at least 1 H on a hydrocarbon is replaced by OH

phenols:

at least 1 H on an aromatic ring is replaced by OH

3-methyl-1-butanolSlide8

Alcohols & phenols: contain the hydroxyl group (-OH)alcohols: at least 1 H on a hydrocarbon is replaced by OH

phenols:

at least 1 H on an aromatic ring is replaced by OH

1,2-butanediolSlide9

ethers: compounds in which an O atom is bonded to 2 organic groups: -C-O-C-

methoxymethane

(dimethyl ether)Slide10

ethers: compounds in which an O atom is bonded to 2 organic groups: -C-O-C-methoxypropane (methyl propyl ether)Slide11

ethers: compounds in which an O atom is bonded to 2 organic groups: -C-O-C-methoxybenzene (methyl phenyl ether)Slide12

Carboxylic acids: compounds that contain the carboxyl group (general formula is R

-COOH

)

butanoic

acidSlide13

Carboxylic acids: compounds that contain the carboxyl group (general formula is R-COOH)

ethanoic acidSlide14

Carboxylic acids: compounds that contain the carboxyl group (general formula is R-COOH)

3-methylpentanoic acidSlide15

Carboxylic acids: compounds that contain the carboxyl group (general formula is R-COOH)

benzoic acidSlide16

amines: derivatives of ammonia (NH3)

in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups

)

ammoniaSlide17

amines: derivatives of ammonia (NH3) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups)

methylamineSlide18

amines: derivatives of ammonia (NH3) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups)

trimethylamineSlide19

amines: derivatives of ammonia (NH3) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups)

2-aminobutaneSlide20

amines: derivatives of ammonia (NH3) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups)

1-amino-3-propylcyclohexaneSlide21

*aniline: the simplest aromatic amine

anilineSlide22

*aniline: the simplest aromatic amine

3,5-dichloroaniline

Naming it “aniline” make this carbon #1 by definitionSlide23

*aniline: the simplest aromatic amine

N,N-dimethylanilineSlide24

Summary of IUPAC rules for naming organic compoundsIUPAC: International Union of Pure and Applied Chemistry International, non-governmental organization that is best known for its system of nomenclature, which is now recognized as the world authority in this field. Slide25

Rule #1: Identify the longest chain of carbon atomsa) The longest chain of carbon atoms gives the stem/root of the name as shown in the table below:

# of C-atoms in longest chain

Stem in IUPAC name

Example

(C

2

H

2n+2 for alkanes)

1

meth-

CH

4

, methane

2

eth-

C

2

H

6

, ethane

3

prop-

C

3

H

8

, propane

4

but-

C

4

H

10

, butane

5

pent-

C

5

H

12

, pentane

6

hex-

C

6

H

14

, hexane

7

hept-

C

7

H

16

, heptane

8

oct-

C

8

H

18

, octane

9

non-

C

9

H

20

,

nonaneSlide26

b) If two chains have equal lengths, pick the one with more branch points.Rule #1: Identify the longest chain of carbon atomsSlide27

Rule #2: Number the carbons in the main chainNumber chain to minimize the position/number of the following in order of priority:thing you’re naming the compound after (double bond if alkene; -OH group if alcohol, etc)

note: for multiple double bonds



-

diene, -triene, -tetraenefirst branch/substituent group If both ends have the same first branching number, then number chain to minimize position of second branch (and then third and so on).if still in need of a tie breaker, minimize # of substituent group that comes first alphabeticallyNote:

in cyclic and aromatic (benzene derivatives) compounds, no number needed if only one substituent. Slide28

Rule #3: Identify the functional group and attach appropriate suffixNote: the name for the stem/root is derived from the longest carbon chain, which may include the carbon of the functional group.Indicating position of the functional group: shown by a number inserted before the functional group ending. The number refers to the carbon atom to which the functional group is attached when the chain is numbered starting at the end that will give the smallest number to the group.Slide29

Class of compound

Functional group

Suffix in IUPAC name

alkane

-anealkene

  -ene

alkyne  

-ynealcohol

-anol

aldehyde

-anal

ketone

-anone

carboxylic acid

-anoic acid

amine

-

anamineSlide30

Rule #4: Identify the side chains or substituent groupsAssign number of carbon at point of attachment.

Side chain/ substituent group

Prefix in IUPAC name

Example

-CH

3

methyl-

2-methylpropane

-C

2

H

5

ethyl

3-ethylpentane

-C

3

H

7

propyl-

4-propylheptane

-F, -

Cl

, -Br, -I

fluoro-, chloro-, bromo-, iodo-

tetrachloromethane

-NH

2

amino-

2-aminoethanioic acidSlide31

Rule #5: Assemble name as a single word  #, substituent, root, suffixList substituents alphabetically (i.e. butyl- before

methyl-

)

If

multiples of one substituent are present: “di-,” “tri-,” “tetra,” etc.Note: “di-,” “tri-,” “tetra,” etc. aren’t part of alphabetical name (triethyl- before dimethyl-)

punctuation: commas between numbers; hyphens between numbers and letters; merged into one word (exception: acid = word #2 for carboxylic acids)