H H H H H H H H | | | | | | | | H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H H H H | | | H - C - C - C - C - H | | | H H H H -

H H H H H H H H | | | | | | | |H - C - C - C - C - C - C - C - C - H | | | | | | | H H H H H H H

H H H | | | H - C - C - C - C - H | | | H H H H - C - H | H - C - H | H

Here’s a structural diagram of a typical hydrocarbonIt has 14 C’s and 30 H’s so the formula isC14H30

since each C is surrounded by 4 bonds typically, for ease of drawing, the H’s are left out to form a carbon skeleton diagram

Find the longest continuous carbon chain. This structure is called the parent chain.

C - C - C - C - C - C - C - C | C - C- C - C |

C |

C

This parent chain has 9 C so it starts with non.If there are no doublebonds it ends with ane

Nonane is the name of the parent chain

To name the parent chain prefixes at the beginning of the word are used. These prefixes are determined by the number of C atoms in the parent chain.

Find the longest continuous carbon chain. This structure is called the parent chain.

C - C - C - C - C - C - C - C | C - C- C - C |

C |

C

If the carbon chain is 1 C starts with meth2 C starts with eth3 C starts with prop4 C starts with but5 C starts with pent6 C starts with hex7 C starts with hept8 C starts with oct9 C starts with non10 C starts with dec

This parent chain has 9 C so it starts with non.If there are no doublebonds it ends with ane

Nonane is the name of the parent chain

C - C - C - C - C - C - C - C | C - C- C - C |

C |

C

Next you must number the parent chainChains can be numbered from either direction so the rule to follow states:Number the chain so the lowest possible number is used when the 1st side chain is encountered

12345

6 7

8

9

98765

43

2

1

Using the red numbers the 1st side chain is encountered at the 5th C

Using the blue numbers the 1st side chain is encountered at the 3rd C

C - C - C - C - C - C - C - C | C - C- C - C |

C |

C

98765

43

2

1

Next, identify the side chains and where they are attached

3 C side chain is called propyl 2 C side

chain is called ethyl

Notice all side chains end in yl

C - C - C - C - C - C - C - C | C - C- C - C |

C |

C

98765

43

2

1

Now lets consider the names which have been determined

Parent chain is nonaneside chains are3-ethyl and5-propylthe complete name is

3-ethyl-5-propylnonaneSide chains appear 1st and are always alphabetized, (ethyl before propyl), parent chain appears last

Now draw the skeleton structure for 5-butyl-6-ethyl-2-methyl decane1st identify the parent chain

5-butyl-6-ethyl-2-methyldecane (decane means 10 C’s with no double bonds

C - C - C - C - C - C - C - C - C - CSide chains are:2-methyl(1 C attached to the 2nd C)

|C

5-butyl4 C’s attached to the 5th C

6-ethyl2C’s attached to the 6th C

|C |C |C |C

|C |C

Now draw the skeleton structure for 3,3-diethyl-2,5,6-trimethylheptane1st identify the parent chain3,3-diethyl -2,5,6-trimethylheptane (heptane means 7C’s with no double bonds

C - C - C - C - C - C - C

Side chains are:3,3-diethyl(2C attached to each side of the 3rd C)

2,5,6-trimethyl1C’s attached to the 2nd, 5th and 6th C

|C |C

C |C |

|C

|C

|C

Name the following:

C C - C C | | |C - C - C - C - C - C - C - C | | | | C C C C

Parent Chain is octane

Side Chains are 2,2,3,4,7,7 hexamethyl6 - ethylFinal Answer is

6 - ethyl - 2,2,3,4,7,7 - hexamethyloctane

Naming Cyclic Hydrocarbons with Side Chains

CH2

CH2

CH2

CH2CH2

What is this structure called?

cyclopentane

CH3

CH3

CH3

Number the carbons in the ring using the lowest possible numbers.

1

23

45

1,2,4-trimethyl

Draw 2,3-diethyl-1-methylcyclohexane

CH2

CH2 CH

CH

CHCH2

CH3

CH2CH3

CH2CH3

Aromatics with Side-Chains

CH2CH2CH3

CH2CH2CH3

Name?1,3-dipropylbenzene

Sometimes compounds are more easily named when the benzene ring is considered to be a side chain.

CH3

CH2

CH

CH

C

CH3

C

CHCH

CHCH

CH

CH3

CH3

CH3

Name?2,2,3-trimethyl-4-phenylhexane

Draw 2,3-dimethyl-2,3-diphenylpentane

CH3

CC

CH2CH3

C

CH CH

CH CH

CH

C

CHCH

CHCH

CH

CH3

CH3

C

C

C

C

C

C

C

Alkyl Halides-Hydrocarbons containing F, Cl, Br, I

When a halogen is introduced into a hydrocarbon molecule naming proceeds as if the halogen were simply a branch. CH3CH2CHCH2CH3

| Clis named3-chloropentanesoCH3CH2CH2CH2CH2CH2Bris named1-bromohexane

Draw the complete structural diagram for4-bromo-2,5-dimethylheptane H H H H H H H | | | | | | |H-C-C -- C-C - C -- C-C-H | | | | | | | H CH3 H Br CH3 H H

(CH3)2CHCH2CHBrCH(CH3)2

named

CH

HCHH

HHCH HCH

CH

BrHCH HC H

H

CH H

CH

HCHH

HHCH HCH

CH

BrHCH HC H

H

CH H

The parent chain isHexanethe rest of it is3 - bromo2,5 - dimethyl, so the complete name is3-bromo-2,5-dimethylhexane

If double bonds are present, the hydrocarbon is still named as if the halogen were absent. F-CH=CH-CH2-CH3 is named 1-fluoro-1-buteneCH3-CH=CH-CH2I is1-iodo-2-buteneCH2-CH=CH-CH2

| |Br Br is named1,4-dibromo-2-butene

The condensed structural diagram for 1-chloro-6-iodo-2,4-hexadiene is

CH2-CH=CH-CH=CH-CH2

| | I Cl

Cis and Trans Isomers

Molecules with double and triple bonds cannot rotate in opposite directions on each side of the double bond so when side chains, like Cl atoms for example, are attached on each side of the double bond 2 different structures are possible.

CH CH

Cl

Cl

CH CH

Cl Cl

cis-1,2-dichloroethene

trans-1,2-dichloroethene

CH3

CH2C

CCH3

Br

Br

Nametrans-2,3-dibromo-2-pentene

CH2 CH2

H Cl

CH2 CH2

H Cl

CH2 CH2

H Cl

CH2 CH2

H Cl

CH2 CH2

H Cl

CH2 CH2

H Cl

CH2 CH2

H Cl

CH3 CH2Cl

C CH

H

H

H

H Cl

C CH

H

H

H

H Cl

C CH

H

H

H

H Cl

C CH

H

H

H

H Cl

C CH

H

H

H

H Cl

C CH

H

H

HH Cl

C CH

H

H

HH Cl

C C

H

H

H

H

H Cl

C2H4 + HCl C2H5Cl

Addition ReactionHydrohalogenation of an Alkene to an alkyl halide

ethene chloroethane

C2H4 + HCl C2H5Cl

Addition ReactionHydrohalogenation of an Alkene to an alkyl halide

ethene chloroethane

Markovnikov’s RuleWhen non-identical atoms are added 2 products are theoretically possible. Experiments show only 1 main product is formed. The H atom will bond to the C atom which already has more H’s attached.

H-CH=CH-CH3 + HBrH2C – CH – CH3 or H2C – CH –CH3

H Br HBr2-bromopropaneMain product 1-bromopropane

The “rich” get “richer”

2H’s x

CC

C

C

H

H

H

HH

HH

H

HBr

Predict the product for the reaction below

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

HH

Br

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

H

HBr

CC

C

C

H

H

H

HH

HH

HH

Br

The H atom will bond to the C atom with the most H atoms already attached.

C

C

C

C

BrH

H

H

H

H

H H

H

H

2-bromobutane

Draw structural diagrams showing the reaction of HF and 1-pentene

HF + C

C

C

C

C

H

H

H H

H

H

H H

H

H

C

C

C

C

CH

H

H

H

F

H

H

H

H H

H

H

2-fluoropentane

CH2 CH2

Cl Cl

CH2 CH2

Cl Cl

CH2 CH2

Cl Cl

CH2 CH2

Cl Cl

CH2 CH2

Cl Cl

CH2 CH2

Cl Cl

CH2 CH2

Cl Cl

CH2 CH2Cl Cl

CClH CH Cl22

C CH

H

H

H

Cl Cl

C CH

H

H

H

Cl Cl

C CH

H

H

H

Cl Cl

C CH

H

H

H

Cl Cl

C CH

H

H

HCl Cl

C CH

H

H

HCl Cl

C C

H

H

H

HCl Cl

C C

H

H

H

H

Cl Cl

C2H4 + Cl22 C2H4Cl2

Addition ReactionHalogenation of an Alkene to an alkyl halide

ethene 1,2-dichloroethane

CC

H

HH

H

HH

Cl Cl

CC

H

HH

H

HH

Cl Cl

CC

H

HH

H

HH

Cl Cl

CC

H

HH

H

HH

Cl Cl

CC

H

HH

H

HH

Cl Cl

CC

H

HH

H

ClH

H Cl

CC

H

HH

H

ClH

Cl Cl

CC

H

HH

H

ClH

Cl Cl

CC

H

HH

H

ClH

Cl Cl

CC

H

HH

H

ClH

Cl Cl

CC

H

HH

H

ClH

Cl Cl

H Cl

CC

H

HH

ClH Cl

H Cl

CC

H

HH

ClH Cl

C2H6 + 2Cl2 C2H4Cl2 +2HCl

Substitution ReactionChanging an Alkane to an alkyl halide

ethane 1,2 dichloroethane

Halogens have large electronegativities so their presence on a hydrocarbon chain creates a polar region which is localized. If they are present in a balanced symmetrical pattern, the polarity is nulified and the molecule is non-polar. (C2Cl6 for example).Alkyl halides have stronger intermolecular forces than their corresponding hydrocarbons due to this polarity, so they have higher MP and BP and are more soluble in polar solvents than hydrocarbons. The more halogenated the hydrocarbon, the greater the polarity and the higher the MP and BP.

are characterized by the presence of an OH group (hydroxyl). The alcohol whose parent hydrocarbon is propane can have two possible structures which are derived by replacing an H atom with an OH group.

H H H | | |H - C - C - C - H | | | H H H

OH

OH

OH OH OH

OH OH

OH

Notice the OH group is either attached to the 1st or the 2nd C so the 2 possible names are 1-propanol

Alcohols end in ______ol.2-propanolOH

H

Name this structureCH3(CH2)7OH1-octanol Name this structureCH3 CH2 CH2 CH CH2 CH2CH2CH3

| CH2 CH2OHWhen a functional group like OH is present find the longest carbon chain which contains the functional group. The OH group is on the 1st carbon.3-propyl-1-heptanol.Name this structure CH3 CH2 CHCH3

| OH2-butanol not 3 butanol is the correct name

CH3 CH2 CH2 CH(OH) CH2 CH3

is named3-hexanolOnce the numbering system is determined by the location of the OH group, other branches, alkyl or halogen are named in the usual way CH3

|CH3 -CH2 - C - OH is named | CH3

2-methyl-2-butanol

CH3 CH2 CH3

| |CH3 C CH2 CH2 CCH3

| | CH3 CH CH3

| OHis named

Find the longest C chain which contains the OH group

2-heptanol3-ethyl-3,6,6-trimethyl-

If a carbon chain has more than one OH group attached it is called a polyhydroxy compound.

Draw a structural diagram of 1,2-ethanediol.CH2 OH |CH2 OH

the common name for this is ethylene glycol the principal component of antifreeze. CH2 OH |CH3CH2 - C-OH | CH2 OH

Its name is2-ethyl-1,2,3-propantriol

The insect repellent “6-12” (2-ethyl-1,3-hexanediol) has the structural formula: H H H H H H | | | | | |H - C - C --- C - C - C - C - H | | | | | | OH CH2 OH H H H | CH3

What is the name of the structure below: OH | CH / \ CH2 CH2

| | CH CH / \ / \ OH CH2 OH

1,3,5-cyclohexanetriol

CH3CH=CH-CH2-OH is named2-buten-1-ol CH2=CH-CH2OH is named

2-propen-1-olthe OH group takes precedence in numbering3-buten-2-ol has the formula: H H H H | | | /H - C - C - C = C | | \ H OH H

If there is a choice of chains, the most unsaturated is chosen as long as it still contains the OH groupExample - What is the name of:CH3 - CH = C - CH2 - OH | CH2CH2CH3

the parent chain is

2 - buten -1- ol

The complete name is

2 - propyl -

Remembering the compounds with triple bonds are called alkynes, the structural diagram for 2-propyn-1-ol is H | H - C - C C - H | OH

CH3-CH2-C-CH2-CH-CH3

| | CH3 CH2OH is2,4 - dimethyl-1-hexanol

The formula for2,2,5-trimethyl-3-hexene-1,5-diol is CH3 OH | | CH2-C-CH=CH-C-CH3

| | |OH CH3 CH3

CH2 CH2

OH H

CH2 CH2

OH H

CH2 CH2

OH H

CH2 CH2

OH H

CH2 CH2

OH H

CH2 CH2

OH H

CH2 CH2

OH H

C

C

OH

HH

H

H

H

ethanol

C CH

H H

H

O

H H

C CH

H H

HO

H H

C CH

H H

HO

H H

C CH

H H

HO

H H

C CH

H H

HOH H

C CH

H H

H

OHH

C2H4 + H2O C2H5OH

Addition ReactionHydration of an Alkene to an alcohol

ethene ethanol

The presence of the OH group makes them polar so they are soluble in water and other polar solvents and can form H bonds which is a stronger intermolecular force that dipole-dipole attractions found between polar molecules.As the non-polar hydrocarbon chain grows in the higher molecular weight alcohols the polarity decreases so the solubility diminishes but they can be used to dissolve both non-polar and polar substances.Larger molecular weight alcohols also have stronger intermolecular forces so BP increases.

Oxygen atoms can bond in the middle of a chain of carbon atoms. When this happens the compounds formed are called ethers.ExampleCH3-CH2-O-CH2-CH2-CH2-CH3

The longest chain is used as the parent chain.

This 4 carbon chain is called butanethe side chain is 2 C’s + the O

The side chain is called ethoxy ethoxybutane

Sketch 1,2-dimethoxycyclopentaneParent chain is cyclopentaneside chains are methoxy attached to consecutive carbons in the 5 Carbon ring

CH2

/ \ CH2 CH-O-CH3

| | CH2---CH-O-CH3

Name this structureCH2=CH-CH-CH2-CH-CH2-CH3

| | CH3-CH2-O O-CH2-CH2-CH3

parent chain is1-hepteneside chains are3-ethoxy and 5-propoxycomplete name is3-ethoxy-5-propoxy-1-heptene

C

CCO

H

HH

H

HH

H

H

CC

CO

H H

HH

H

H

H

H

2-propanol

C

CCO

H

HH

H

HH

H

H

CC

CO

H H

HH

H

H

H

H

2-propanol

C

CCO

H

HH

H

HH

H

H

CC

CO

H H

HH

H

H

H

H

2-propanol

C

CCO

H

HH

H

HH

H

H

CC

CO

H H

HH

H

H

H

H

2-propanol

C

CC

H

HH

H

HH

H

CC

CO

H

HH

H

H

H

H

O

HH

CC

CO

CH H

HH

H

H

H

H

C CH

H H H

H

H

O

HH

2-methylethoxypropane

2C3H7OH C6H14O +H2O

Dehydration of Alcohols to Ethers

2-propanol 2- methylethoxy

propane

H2SO4

The difference in En of C and O, and the V shape of the C – O – C bond make ethers slightly polar. Their MP and BP lie in between those of corresponding alcohols and hydrocarbons. They mix readily with both polar and nonpolar substances so make excellent solvents for organic reactions. The C-O bond is quite stable making ethers generally unreactive, another property of a good solvent.

Both these families have C = O groups replacing a H atom on the carbon chains. Aldehydes have this C = O group at the end of a chain, Ketones have the C = O group in the middle portion of the chain. Here are some examples of aldehydes and ketones. Decide which is which.

A. CH3HC=O B. CH3CH2C = O | CH3

C. (CH3)2CHCCH(CH3)2

|| O

D. HCHO

aldehyde

aldehyde

ketone

ketone

E. CH3COCH3 F. HCOC2H5

aldehydeketone

Aldehydes end in _______________alKetones end in _______________oneethanal isCH3-C=O | Hpropanone is

CH3-C-CH3

|| O

Pentanone has 2 possible structures.They are

CH3CCH2CH2CH3

|| O andCH3CH2CCH2CH3

|| O

2 - pentanone

3 - pentanone

Name this structure CH3

|O=CCHCH2CH3

| CH3

the parent chain is

3-methyl-2-pentanone

2,3-hexanedione is

C - C - C - C - C - C || || O O

1,4-cyclohexanedione is CH2

/ \ CH2 C=O | |O=C CH2

\ / CH2

3-penten-2-one isThe functional group takes precedence over the double bondC - C - C = C - C || O

3-hydroxypentanal is

C - C - C - C - C || |O OH

5-chloro-3-heptenal is

C - C - C = C - C - C - C || |O Cl

Name thisCH3C=O | CH2CH-CH3

| I

4-iodo-2-pentanone

2,5-heptadien-4-one has the structural formula

CH3CH=CH-C-CH=CHCH3

|| O

C COH

H H

CH

H H

HH

KMnO4 or Cr2O72- in H2SO4

O

1-propanol

C COH

H H

CH

H H

HH


O

1-propanol

C COH

H H

CH

H H

HH


O

C COH

H H

CH

H H

HH


O

C COH

H H

CH

H H

HH


O

C COH

H H

CH

H H

HH


O


HH

O

C COH

H

CH

H

HH


HH

O

C COH

H

CH

H

HH


HH

O

C COH

H

CH

H

HHpropanal

dehydration reaction

C

CCOH

H

HH

H

HH

H


O

2-propanol

C

CCOH

H

HH

H

HH

H


O

2-propanol

C

CCOH

H

HH

H

HH

H


O

2-propanol

C

CCOH

H

HH

H

HH

H


O

2-propanol

C

CCOH

H

HH

H

HH

H


O

2-propanol

C

CCOH

H

HH

H

HH

H


O

C

CCOH

H

HH

H

HH

H


O

C

CCO

HH

HH

H

HH

H


O


H

HO

C

CCO

H

HH

H

HH

propanone

Notice when the OH group is not on the end a ketone is made

C3H7OH + O C3H6O + H2O2-propanol propanone

Oxidation of Alcohols to Aldehydes or Ketones

1-propanol propanal

The C = O bond is polar so aldehydes and ketones are soluble in water and their MP and BP lie between corresponding hydrocarbons and alcohols since the O – H bond is more polar. They also can mix with non-polar substances due to the presence of hydrocarbon chains. The longer the chains the more non-polar they are, the less soluble they are in polar solvents and the more soluble they are in non-polar solvents.Again as their molecular weights increase so do their MP and BP due to increased VdW forces.

Ethanoic Acid isCH3C=O | OHthe name of this isCH3CH2CH=CHCOOH2-pentenoic acid

4-hydroxy-3-iodo-2-heptenoic acid is

C - C - C - C - C = C - C = O | | | OH I OH

Name thisCH3-CH-CH2-CH2-CH3

| COOH2-methylpentanoic acid

C COH

H

CH

H

HHpropanal


O

C COH

H

CH

H

HHpropanal


O

C COH

H

CH

H

HHpropanal


O

C COH

H

CH

H

HHpropanal


O

C COH

H

CH

H

HHpropanal


O

C COH

H

CH

H

HHpropanal


O

C CO

H

H

CH

H

HHpropanal


O

`

C CO

H

H

CH

H

HHpropanal


O

`

C CO

H

H

CH

H

HHPropanoic acid


O

`

C3H6O + O C2H5COOHpropanal propanoic acid

Oxidation of Aldehydes to Carboxylic Acids

Organic acids are polar and form H bonds so they are soluble in water. As molecular weights increase, intermolecular forces increase so BP and MP increase.As the hydrocarbon chain grows, the polarity decreases so the solubility in polar solvents decrease.

C C

O

H

H

H H

H

H

C C C

O

OH

H

H

H

H

H

C C

O

H

H

H H

H

H

C C C

O

OH

H

H

H

H

H

C C

O

H

H

H H

H

H

C C C

O

OH

H

H

H

H

H

C C

O

H

H

H H

H

H

C C C

O

OH

H

H

H

H

H

C C

O

H

H

H H

H

H

C C C

O

OH

H

H

H

H

H

C C

O

H

H

H H

H

H

C C C

O

OH

H

H

H

H

H

C C

O

H

H

H H

H

H

C C C

O

OH

H

H

H

H

H

C C

O

H

H

H

H

H

C C C

O

H

H

H

H

H

HO

H

C C

O

H

H

H

H

H

C C C

O

H

H

H

H

H

HO

H

C C

O

H

H

H

H

H

C C C

O

H

H

H

H

H

HO

H

C C

O

H

H

H

H

H

C

C

C O

H

H

H

H

HO

H

H

C C

O

H

H

H

H

H

C

C

C O

H

H

H

H

HO

H

H

ethylpropanoate

Making Esters from Alcohols and Acids

C2H5OH + C2H55COOH

C2H5COOC2H5 + H2O

O = C - C - C - C - C | OH

C - C - C - C - OH

Alcohol is called Acid is called

1-butanol Pentanoic acidWhen they combine H2O is removed (a dehydration synthesis)

O = C - C - C - C - C | OH

C - C - C - C - OH

C - C - C - C - OH

C - C - C - C - OH

O = C - C - C - C - C | O | C - C - C - C

O = C - C - C - C - C | O | C - C - C - C

When naming esters you name the alcohol 1st (remove the letters anol from the end and add the letters yl at the end.If the alcohol is 1-butanol then the name is 1-butyl.The acid name is second. If the acid is pentanoic drop the last 3 letters (oic) and add the letters oate. In this instance it becomes pentanoate. The complete name becomes

1-butyl pentanoate

O = C - C - C - C | O | C - C

This ester’s name is

Remember alcohol1st

Ethanol becomes ethyl

Acid 2nd Butanoic becomes butanoate

Ethyl butanoateRemember the double bonded oxygen atom is always joined to the acid

What is this ester’s name?

O = C - C | O | C - C - C - C - C

Remember alcohol1st

2-pentanol becomes 2-pentyl

Acid 2nd ethanoic becomes ethanoate

2-pentylethanoate

Draw the structural diagram for 2,3,3-trichloro-2-hexylmethanoate

Remember alcohol1st

Cl Cl | |C - C - C - C - C - C | | OH Cl

OH |O = C

Cl Cl | |C - C - C - C - C - C | | Cl O

|O = C

Esters lack the OH group from the parent acid and alcohol so they are less polar.This means they have lower MP and BP than their corresponding acids and alcohols are less soluble in water and are not acidic.Smaller molecular weight esters have relatively weak intermolecular forces so they have strong odours.

NH2 groups can be attached as side chains to carbon parent chains. These groups are called amines. Here is an example.1,2-diaminopropane isCH2-CH-CH3

| | NH2 NH2

What is the name of this structure?F-C=C-C-C-C-NH2

| NH2

3,5-diamino-1-fluoro-1-pentenenotice the double bond takes precedence over the side chains. When a functional group is present like alcohols (OH), aldehydes (C=O), ketones, or acids, they take precedence over the double or triple bonds.

The hydrogens on the amines can be replaced by methyls (CH3), ethyls (C2H5) , halides (F), etc. CH3-CH-CH3

| N / \

CH3 C2H5H H

When this happens the side chain is called N-ethyl-N-methyl-2-aminopropane

C C

H

H

Cl

H

H

H

NH

HH

C C

H

H

Cl

H

H

H

NH

HH

C C

H

H

Cl

H

H

H

NH

HH

C C

H

H

Cl

H

H

H

NH

HH

C C

H

H

Cl

H

H

H

NH

HH

C C

H

H

Cl

H

H

H

NH

HH

C C

H

H

Cl

H

H

H

NH

HH

C C

H

H

H

H

H

NH H

Cl

H

C C

H

H

H

H

HN

H H

Cl

H

C C

H

H

H

H

HN

H H

Cl

H

C C

H

H

H

H

HN

H H

Cl

H

aminoethane

Making Amines From Alkyl Halides

CH3CH2Cl + NH3 C2H5NH2 + HCl

Amines are named as side chains.Name this compound

CH3C

CH

CH

CH3

NH2

NH2

Parent chain is 2-pentene4,4-diamino-2-pentene

Draw 2,2 diamino-6-methyl-3,5-octadiene

CH3C

CH

CH

CH

NH2

NH2

C

CH2

CH3

CH3

N – H and C – H bonds are both polar and N – H bonds exhibit H bonding properties so amines are quite soluble in water.Neither bond is as polar as O – H so they have lower MP and BP than their corresponding alcohols. As molecular weight increases so does BP and MP unless no H bonding occurs. Match these MP to the diagrams 8oC, -33oC, 6oC.

NH

HH N

H

CH3H N

CH3

CH3H

Remember the carboxylic acids

Ethanoic Acid isCH3C=O |

OH

If the OH group is replaced by an amine the resulting functional group is called an amide. Amides are named from the parent chain

NH2

Ethanamide

3-ethyl-2-pentenamide isCH3-CH2-CH=CH-C=O | | C2H5 N / \ H H

If the H’s on the NH2 are replaced by a methyl and an ethylCH3-CH2-CH=CH-C=O | | C2H5 N / \H HCH3 C2H5The name is

N-ethyl-N-methyl-3-ethyl-2-pentenamide

Sketch the followingN-ethylbutanamideCH3-CH2-CH2-C=O | N / \ C2H5 H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

H H

CCC

O

OH

H

H

H

H

H

C C

H

H

H

N

H

H

HCCC

O

H

H

H

H

HH

OH

C C

H

H

H

N

H

H

H CCC

O

H

H

H

H

H

H

OH

H

OH

C C

H

H

H

N

H

H

H CCC

O

H

H

H

H

H

H

OH

C C

H

H

H

N

H

H

H CCC

O

H

H

H

H

H

N-ethylpropanamide

Making Amides From Amines and Acids

C2H5NH2 + C2H5CO2H C2H5CONHC2H5

+ H2O

Amides are generally insoluble in water due to the relative cancellation of the 4 different polar regions (the two N – H s, the C = O and the C - N). The lower molecular weight amides are slightly soluble due to the presence of H bonding.Amides which have alkyl groups attached to the N atom have weaker intermolecular forces (due to lack of H bonding) so have lower MP and BP.The lone pair of electrons found on the N atom makes it attractive to H atoms so amines are weak bases.

NO2 groups can be attached as side chains to carbon parent chains. These nitro groups as named as side chains much like halogens (Cl), ethers (OCH3) and hydroxys (OH). Here is an example.3-nitro-1-hexene has the structureCH2=CH-CH-CH2-CH2-CH3

| NO2

Sketch 1-methyl-2,3,4-trinitro-1,3,5-cyclohexatriene (TNT)

C C C C C C

CH3

NO2

NO2 H

NO2 H

This structure is also called trinitrotoluene (TNT). A benzene ring with a methyl group is called toluene. Benzene is also drawn like this

and when functional groups are attached at adjacent locations the prefix ortho(oo) is used. Here are examples of o-o-dichlorobenzene

Cl

ClCl

Cl

If functional groups are on carbons separated by one empty carbon the prefix used is meta (m) Here are examples of m --difluorobenzene.

F F

F

FIf functional groups are on carbons separated by two empty carbons the prefix used is para (p) Here are examples of p --dibromobenzene.

Br

Br

Br

Br

20 different amino acids are used to assemble protein. Like the name implies amino acids have amino and carboxylic acid groups on adjacent carbons.

R OH | | H-C-C=O | NH2

Each of the 20 different amino acids has a different R group.

If the R group is methyl the amino acid is called alanine. Its structure is

CH3 OH | | H-C-C=O | NH2

If the rules presented previously were used to name alanine it would be called2 - aminopropanoic acid

If serine is named 2-amino-3-hydroxypropanoic acid what is its structure?

H OH | |OH-CH2-C-C=O | NH2

2-amino-3-hydroxypropanoic acid

Most of the dry mass of living organisms is composed of proteins. Proteins are composed of long chains of the 20 different amino acids linked end to end. Here is an example of how amino acids are chemically bonded. The product produced from 2 amino acids is called a dipeptide. Here is how dipeptides form.

H OH | | H-C-C=O | NH2

CH3 OH | | H-C-C=O | N / \ H H

When 2 different aminoacids combine the amino group of one amino acid always reacts with the carboxyl group of the other amino acid.

Notice water is eliminated so this kind of reaction is called a dehydration synthesis. The product is called a dipeptide.

H OH | | H-C-C=O | NH2

CH3 OH | | H-C-C=O | N / \ H H

CH3 OH | | H-C-C=O | N \ H H |H-C-C=O | NH2

H2O +

Remember a peptide linkage occurs between the amino group of one amino acid and the carboxyl group of another. Water is always eliminated in this dehydration synthesis. Show how a peptide bond forms from 2 amino acids if one has an R group which is a hydroxy and the other’s R group is an ethyl.

OH OH | | H-C-C=O | H-N-H C2H5 OH

| | H-C-C=O | H-N-H

OH OH | | H-C-C=O | N-H C2H5

| H-C-C=O | H-N-H

+ H20

To watch a movie showing polypeptide formation click here

Making Aspartame - A dipeptide

PhenylalanineSystematic name?2-amino-3-phenyl-propanoic acid

O

NH2

OH

180x's sweeter than sugar

http://en.wikipedia.org/wiki/Aspartame_controversy

Making Aspartame - A dipeptide

Aspartic acidSystematic name?Aminobutandioic acid

O

ONH2

OH

OH

Making Aspartame

O

ONH2

OH

OH

O

N

OH

H H

Making Aspartame

O

ONH2

OH

OH

O

N

OH

H H

Making Aspartame

O

ONH2

OH

OH

O

N

OH

H H

Making Aspartame

O

HN

OH

O

ONH2

OH

Methyl ester of a Dipeptide

O

HN

OH

O

ONH2

OH

CH3

OH

methanol


O

HN

OH

O

ONH2

OH

CH3

OH

methanol


O

HN

OH

O

ONH2

OH

CH3

OH

methanol


O

HN

O

O

ONH2

OH

CH3


O

HN

O

O

ONH2

OH

CH3

10% of ingested aspartame is changed into methanol which is poisonousDoseage from 1 diet drink is minimalSucralose is probably better as an artificial sweetner.Show where this hydrolysis happens.

http://en.wikipedia.org/wiki/Aspartame_controversy


O

HN

O

O

ONH2

OH

CH3

HO

H


O

HN

OH

O

ONH2

OH

CH3

OH

Methanol is further oxidized into methanal, then methanoic acid. Draw these reactions.Methanoic acid can be toxic at high levels due to its inhibition of cytochrome c oxidase the last enzyme in the electron transport chain in the mitochondria. It transfers the electrons to oxygen. Complete inhibition is fatal.

sucralose

Sucrose -white sugar

Notice the similarites between sucralose and sucrose. Compare to aspartame

sucralose

Sucrose -white sugar

O

HN

O

O

ONH2

OH

CH3

Aspartame

Making Acetylsalicylic Acid (ASA) Aspirin

Salicylic acid Acetic anhydrideEthanoyl ethanoate

ASA

OH

OOH

O

O

O

CH3

CH3

O

OOH

O

CH3

CH3

O

OH+

+

Ethanoic acidAcetic acid5% is vinegar

http://en.wikipedia.org/wiki/Aspirin

Let's focus on the acetic anhydride.

O

OO

CH3 CH3

All anhydrides are created by the elimination of water. This anhydride is formed by the reaction of 2 acetic acid molecules with the elimination of water (dehydration)

CH3

O

OH

CH3

O

OH


O

OO

CH3 CH3


CH3

O

OH

CH3

O

OH


O

OO

CH3 CH3


O

OO

CH3 CH3


O

OO

CH3 CH3


O

OO

CH3 CH3

When an anhydride is placed in water it will undergo the reverse reaction (hydrolysis). Water is added and it reforms the 2 original molecules, in this case the ethanoic acid.

O

OO

CH3 CH3

OH

H


O

OO

CH3 CH3


O

OO

CH3 CH3


O

CH3 OH

OHH

O

CH3


O

OO

CH3 CH3


O

OO

CH3 CH3


O

CH3 OH

OH

H

O

CH3


O

OO

CH3 CH3


O

OO

CH3 CH3


O

CH3 OH OH

H

O

CH3


O

OO

CH3 CH3


O

OO

CH3 CH3


O

CH3 OH

O

CH3OH

Now the ethanoic acid can undergo an esterification with the alcohol group of the salicylic acid to form the ASA

OH

OOH

CH3

O

OH


OH

OOH

CH3

O

OH


OH

OOH

CH3

O

OH


O

OOH

CH3

O

ASA will sometimes smell like alcohol. This happens when the ester is hydrolyzed by water to reform the salicylic acid and ethanoic acid

O

OOH

CH3

O


O

OOH

CH3

O

OH

H


O

OOH

CH3

OOH

H


OOH

OH

CH3

O

OH


OOH

OH

CH3

O

OH

Nylon is composed of gigantic molecules made up of a repeating subunit called a monomer. These extremely large molecules made up of large numbers of monomers are called polymers. Dupont, in Kingston, makes a kind of nylon called nylon 6,6. It is made from a 6 carbon dicarboxylic acid and a 6 carbon diamino compound.

1,6-diaminohexane (hexamethylene diamine) is one of these compounds and hexandioic acid (adipic acid) is the other. These molecules are combined end to end by releasing water in a dehydration synthesis. Show how this is done.

O=C-(CH2)4-C=O | | OH OH

hexandioic acid

CH2-(CH2)4-CH2

| |H-N-H H-N-H

1,6-diaminohexane

O=C-(CH2)4-C-N-CH2-(CH2)4-CH2

| || | | OH O H H-N-H n

This n means this basic monomer is repeated over and overTo watch a movie click here.

Polymers made by the removal of water are called condensation polymers.Polyesters, like Dacron, are examples of this type of polymer.Esters are made by combining alcohols and acids. To watch a movie of polyester formation click here

Dacron is made from 1,2-ethanediol (ethylene glycol) and paradibenzoic acid (p-phthalic acid). Show how this polymer is made from these 2 monomers.

C

O

OHC

O

OH CH2 CH2OH OH C

O

OHC

O

OH CH2 CH2OH OH

C

O

O CH2 CH2 O CH

O

C

O

OHC

O

O CH2 CH2 OH

Addition Polymerization

Alkene monomers can be combined by breaking double bonds. For movie click here.

C C

H

H H

H

C C

H

H H

H

C C

H

H H

H

+ +

C C C C C CH

HH

H

H H

HH

HH

HH

H H

polyethylene

ethene

Addition polymerization has 3 stepsInitiation - a peroxide becomes a free radical( a compound with an unshared electron)When the free radical collides with a monomer it steals only 1e1- from the double bond leaving behind another free radical. This begins the 2nd stage called elongation. The chain continues to grow until 2 free radicals collide and form a stable polymer. This stage is called the termination of the polymerization.

Show how addition polymers can be made from Propene, chloroethene, and phenylethene (styrene).These polymers are called polypropylene, polyvinyl chloride, and polystyrene.

CC

C H

HH

H

H

H

CC

C H

HH

H

H

H

CC

C H

HH

H

H

H

+ +

polypropylene

propene

CH3

CHCH2

CH

CH2

CH2

CH3 CH3CH3

H H

C C

CH3Hn

chloroethene

CH CH2

Cl+

CH CH2

Cl+

CH CH2

Cl

CH2CH2

CHCH2

CHCH3

Cl Cl Cl

Polyvinyl chloride (PVC)

H H

C C

H Cl n

Phenylethene (styrene)CH CH2

+

CH CH2

+

CH CH2

| | | | | |-C – C – C – C – C – C – | | | | | |

polystyrene

H H

C C

H n

Addition polymerization occurs in 3 stages:Initiation, propagation and termination.An initiating molecule like peroxide falls apart and makes a free radical with a single electron. This highly reactive particle starts the polymerization process. To go to a web site and read more click here.

http://www.pslc.ws/macrogcss/radical.html

Plastics are polymers made from monomers of substituted ethene.Examples include: Teflon Plexiglass

C C

F

F F

F

CH2 CH

C O

OCH3

F F

C C

F F n

H H

C C

H COOCH3 n

Methyl-2-propenoate1-methoxy-2-propenaltetrafluoroethene

CH2C CH CH2

CH3

CH2C CH CH2

Cl

Monomers used to make synthetic rubber

isoprene neoprene

Name these monomers.

2-methyl-1,3-butadiene 2-chloro-1,3-butadiene

The presence of the more electronegative Cl makes it more polar and less miscible with other hydrocarbons.

monomer + monomer + monomer + monomerpolymer

O

OH

OH

OH OH

OH

+O

OH

OH

OH OH

OH

+O

OH

OH

OH OH

OH

+

Carbohydrate Polymers – starch, cellulose, glycogen

The orientation of these bonds and the degree of cross-linking determines what it is.

Typical Fats (Triglycerides)

glycerolC

O

C

C

C

C

OH

CH2

CH2

CH2

CH2

CH2CH2

CH2 CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

Linoleic acid, (omega 6)

C

O

C

C

C CC

C

OH

CH2

CH2

CH2

CH2

CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

H

H

Linolenic acid,

(omega 3)

CO

C

C

OH

CH2CH2

CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

Oleic acid (monounsaturate)

CH2

CH

CH2

OH

OH

OH

Typical Fats (Triglycerides)

glycerolC

O

C

C

C

C

OH

CH2

CH2

CH2

CH2

CH2CH2

CH2 CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

Linoleic acid, (omega 6)

C

O

C

C

C CC

C

OH

CH2

CH2

CH2

CH2

CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

H

H

Linolenic acid,

(omega 3)

CO

C

C

OH

CH2CH2

CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

Oleic acid (monounsaturate)

CH2

CH

CH2

OH

OH

OH

Soap Making Saponification

C

O

C

C

C

C

OH

CH2

CH2

CH2

CH2

CH2CH2

CH2 CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

C

O

C

C

C CC

C

OH

CH2

CH2

CH2

CH2

CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

H

H

CO

C

C

OH

CH2CH2

CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

CH2

CH

CH2

OH

OH

OH

+ NaOH

+ NaOH

+ NaOH

Soap Making Saponification

C

O

C

C

C

C

OH

CH2

CH2

CH2

CH2

CH2CH2

CH2 CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

C

O

C

C

C CC

C

OH

CH2

CH2

CH2

CH2

CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

H

H

H

H

CO

C

C

OH

CH2CH2

CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2CH2

CH2

CH3

H

H

CH2

CH

CH2

OH

OH

OH

Na

Na

Na

CH2

CH

CH2

OH

OH

OH

soap glycerolNa

Na

Na

Most soaps are made from palmitin and stearin from palm oil and olive oil.

CO OH

CH2CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2CH2

CH2CH2

CH2 CH3

CO

OH

CH2

CH2

CH2CH2

CH2

CH2

CH2CH2

CH2

CH2CH2

CH2CH2

CH2

CH3

Stearic acid

Palmitic acid

Show, using structural diagrams, how sodium stearate is made. See pg. 134

There are 2 classes of fats which are essential in the human diet because they cannot be biosynthesized by the human body. These fats are called essential fatty acids (EFA) and as the name implies they contain the carboxyl functional group (COOH). They fall into 2 categories omega 3 and omega 6. All of these essential fatty acids are unsaturates.Essential omega 3 fatty acids include:

α-linolenic acid (ALA), eicosapentaenoic acid (EPA), anddocosahexaenoic acid (DHA). alpha-linolenic acid (18:3, ALA), eicosapentaenoic acid (20:5, EPA), and docosahexaenoic acid (22:6, DHA). These three polyunsaturates have either 3, 5 or 6 double bonds in a carbon chain of 18, 20 or 22 carbon atoms, respectively. All double bonds are in the cis-configuration, i.e. the 2 H atoms are on the same side of the double bond.

http://www.answers.com/topic/alpha-linolenic-acid



http://www.answers.com/topic/eicosapentaenoic-acid

http://www.answers.com/topic/eicosapentaenoic-acid

http://www.answers.com/topic/docosahexaenoic-acid-2

http://www.answers.com/topic/docosahexaenoic-acid-2

http://www.answers.com/topic/polyunsaturated-fat-2

http://www.answers.com/topic/cis-3

ALA – alpha-linolenic acid (18:3) (18 carbons, 3 double bonds at positions 3,6,9 from the terminal methyl end; found in (flax seed oil)EPA – Eicosahexaenoic acid (20:5) 3,6,9,12,15DHA - Docosohexanoic acid (22:6) 3,6,9,12,15,18 ?All three found in seaweed, cold water fish

Shortening is a semisolid fat used in food preparation, especially baked goods, and is so called because it inhibits the formation of long gluten strands in wheat-based doughs, giving them a "short" texture (as in shortbread). Shortening can be made from animal fat (lard), but is more commonly a hydrogenated vegetable oil that is solid at room temperature.

http://www.answers.com/topic/fat

http://www.answers.com/topic/gluten

http://www.answers.com/topic/wheat

http://www.answers.com/topic/dough

http://www.answers.com/topic/shortbread

http://www.answers.com/topic/lard

http://www.answers.com/topic/hydrogenation

http://www.answers.com/topic/vegetable-oil

Shortening has a higher smoke point than butter and margarine, and it has 100% fat content, compared to 80% for butter and margarine. Crisco, a popular brand, was first produced in 1911.

Despite its worldwide usage and availability, vegetable shortening is believed to be damaging to human health since it generally contains trans fats.

Denmark banned it from foods in 2003.

http://www.answers.com/topic/smoke-point

http://www.answers.com/topic/butter

http://www.answers.com/topic/margarine

http://www.answers.com/topic/crisco

http://www.answers.com/topic/trans-fatty-acid

Lard - rendered and clarified pork fat, the quality of which depends on the area the fat came from and the method of rendering. The very best is leaf lard, which comes from the fat around the animal's kidneys. The Nutritional Value for: lard

QuantityCarbs

(grams)Protein(grams)

Cholesterol(milligrams

)

Weight(grams)

Fat(grams)

Saturated Fat

(grams)1 cup 0 0 195 205 205 80.4

1 tbsp 0 0 12 13 13 5.1

Toward the late 20th century lard began to be regarded as less healthy than vegetable oils such as olive and sunflower due to its high saturated fatty acid and cholesterol content.

http://www.answers.com/topic/20th-century

http://www.answers.com/topic/vegetable-oil

http://www.answers.com/topic/olive-oil

http://www.answers.com/topic/sunflower

Tallow is a solid fat extracted from the tissues and fatty deposits of animals, especially from suet (the fat of cattle and sheep). Pure tallow is white, odorless and tasteless; it consists chiefly of triglycerides of stearic (CH3(CH2)16COOH ), palmitic

(CH3(CH2)14COOH ), and oleic acids (18 carbon,

monounsaturated, omega 9 fatty acid). Draw the carbon skeleton.

http://www.answers.com/topic/triglyceride

A triglyceride is made by an esterification involving 1,2,3-propantriol and 3 fatty acids. Show how a triglyceride is made from oleic, stearic and palmitic acids.

Tallow is usually obtained commercially by heating suet (the hard fatty tissues around the kidneys of cattle and sheep) under pressure in closed vessels. Tallow is used to make soap and candles. It was formerly in common use as a lubricant.

The Nutritional Value for: butter

Description QuantityCholesterol(milligrams

)

Weight(grams)

Fat(grams)

Saturated Fat

(grams)salted 1 PAT 11 5 4 2.5

salted 1 tbsp 31 14 11 7.1

salted 1/2 cup 247 113 92 57.1

unsalted 1 PAT 11 5 4 2.5

unsalted 1 tbsp 31 14 11 7.1

unsalted 1/2 cup 247 113 92 57.1

but·ter (bŭt'ər)n.

1.A soft yellowish or whitish emulsion of butterfat, water, air, and sometimes salt, churned from milk or cream and processed for use in cooking and as a food.

canola oil (kə′nōl·ə ′öil) (food engineering) An edible vegetable oil derived from rapeseed that is low in saturated fatty acids (less than 7%), high in monosaturated fatty acids (60%), and high in polyunsaturated fatty acids (30%).Here's a comparison of some to the more common fats and oils.

The lower the saturated fat, the better

For more information click here

http://www.americanheart.org/presenter.jhtml?identifier=532

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