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All Organic Compounds

Hydrocarbons Hydrocarbon Derivatives

Standard Hydrocarbons with CxHx

Hydrocarbons..(C’s and H’s) BUT ALSO other elements.

Organic Halides: are when 1 or more hydrogens have been replaced by a halogen (Group 17; F, Cl, Br, I)

The element itself (Organic Halide) is its own functional group and is named the same as any other branch group.

1 2

Practice (Easy)

1234567

***Name the side branches alphabetically just like with ethy and methy, etc.***

Practice (Cyclo/Benzene)

This type of reaction occurs when UNSATURATED hydrocarbons react with diatomic molecules like;

H2

Cl2

Br2

I2

HBrHClHI

The addition of these diatomic molecules saturate the

hydrocarbon…..breaks the double or triple bonds and adds BOTH onto the chain.

H H

***Addition of H2 breaks the double bond and adds the hydrogens onto the hydrocarbon.***

***For every diatomic molecule you add to a UNSATURATED hydrocarbon it break a bond…so it breaks the “unsaturations” step by step.***

ClH

Step 1

ClH

Step 2

2, 2 – dichloropropane

Cl

H

This type of reaction occurs when SATURATED hydrocarbons react with diatomic molecules like;

H2

Cl2

Br2

I2

HBrHClHI

The substitution of these diatomic molecules trade places with hydrogens already in the

hydrocarbon…..breaks the SINGLE BOND and adds ONE onto the chain.

The second joins with substituted element and forms another compound that leaves the hydrocarbon chain.

Just indicates a common catalyst…DOES NOT MAKE A DIFFERENCE!!!

Cl

Such as;

1. Higher Solubility in water.2. Increased boiling point . 3. Short-Chain alcohols (less than 3 C’s are VERY soluble.4. Long chain alcohols (more than 5) are slightly soluble.

Adding an alcohol(OH-) Functional Group to a hydrocarbon drastically changes the properties of the hydrocarbon.

Methanol and EthanolMethanol (CH3OH) AND Ethanol (CH3CH2OH) are the two most common alcohols.

***Because Methanol and Ethanol only differ from one another by a “CH2” they are part of a

“homologous series”.***

Homologous Series:A series of compounds that only differ by a single repeated “group”.

CH3OH CH3CH2OH CH3CH2CH2OHCH3CH2CH2CH2OHMethanol Ethanol Propanol Butanol

Alcohol…Alcohol was is made by fermentation (yeast, baking, making bread).

Alcohol is poisonous, the “drunk” feeling is the feeling of being poisoned.

The disorientation and loss of motor functions (stumbling) is because YOU ARE BEING POISONED!

Ethanol CH3CH2OH is the ONLY alcohol that wont outright kill you.

So…..DON’T TRY TO MAKE IT….IT COULD BE WRONG.

Alcohol…Alcohol added to fuel to help it burn more efficiently.

Alcohol often added to fuel to as gas line antifreeze.

CH3OH (methanol) is TOXIC.

Add methanol to Ethanol (alcohol you could drink) makes IT TOXIC TOO.

Ethanol used in;Lacquers.Varnishes.Perfume.Synthetic Flavours.

Naming AlcoholsHydrocarbons that contain alcohols are named THE SAME way as usual.

1. You name the longest parent chain.2. You use –ane –ene –yne for single, double, triple bonds.**You number the hydrocarbon ‘Parent Chain” so branches are on lowest carbon numbers****Number the carbons so ALCOHOL is on the lowest number possible** 3. You add “–ol” on the end of a hydrocarbon to show an alcohol (OH) functional group is present.

-C-C-C-C-C-C-C-OHH H

H

H

HH

H

H H

HH

HH

H

H

7 Carbons long

Hept

All single bonds

an

1234567

Number carbons so OH on lowest number.

-1-ol

***Its very common to just NOT put -1- for alcohols on the end of hydrocarbons***

Heptanol

Multiple Alcohols***When there is more than 1 alcohol functional group in a hydrocarbon you describe it the same as you would if there were multiple F’s or Br’s (Halide groups).***Diol -----2Triol-----3

***Make sure if you use “di” you have listed two places….1,2 or 2,5..3,4…etc****

***Make sure if you use “tri” you have listed three places….1,2,3 or 2,2,5..3,5,5…etc****

H--C--C--C--C--C--HH

H

OH

H

HH

OHH

H

H12345

Practice

5 Carbons long

Pent

--

A DOUBLE BOND!!

-1-ene

Number carbons so double bond on lowest number.

Alcohol groups on 2 different carbons.

diol

State which carbon alcohol groups are on.

-2,4-

AlcoholsPrimary, Secondary, Tertiary

Whether an alcohol containing hydrocarbon is considered primary, secondary, or tertiary is dependant on the Carbon that the OH group is attached to.

H--C--C--C--C--C--OHH

H

H

H

HH

H H

H

H

The carbon that the OH group is attached to make this a primary alcohol.

Carbon connect to ONE other carbon makes it primary.

AlcoholsPrimary, Secondary, Tertiary

Whether an alcohol containing hydrocarbon is considered primary, secondary, or tertiary is dependant on the Carbon that the OH group is attached to.

H--C--C--C--C--C--HH

H

H

H

OHH

H H

H

H

The carbon that the OH group is attached to make this a secondary alcohol.

Carbon connect to TWO other carbon makes it secondary.

AlcoholsPrimary, Secondary, Tertiary

Whether an alcohol containing hydrocarbon is considered primary, secondary, or tertiary is dependant on the Carbon that the OH group is attached to.

H--C--C--C--C--C--HH

H

H

H

HOH

H H

H

--C-- The carbon that the OH group is

attached to make this a Tertiary alcohol.

Carbon connect to

THREE other carbon makes it secondary.

HH

H

AlcoholsCombination Practice

Whether an alcohol containing hydrocarbon is considered primary, secondary, or tertiary is dependant on the Carbon that the OH group is attached to.

H--C--C--C--C--C--HH

H

H

H

HOH

H H

H

--C--HH

H

12345

5 Carbons long.

an

All SINGLE bonds.

pent

OH on carbon 3.

-3-ol

CH3 group (methyl) on carbon 3.

3-methyl

Practice Cyclo/Benzene

Alcohols

OH

OH

Cyclopentane-1,2-diolOr

O-cyclopentane-diol

OH

OH

Cyclohexane-1,3-diolOr

M-cyclohexane-diol

Practice Cyclo/Benzene

Alcohols

OH

OH

Cyclopentane-1,2-diolOr

O-cyclopentane-diol

Elimination Reactions

It is often very useful to be able to create alkenes and alkynes from alkanes.

This can be done in TWO ways;

1. Ethene produced from Ethane Cracking

2. Ethene produced by Ethane Elimination Reactions.

Ethane cracking is a special hydrocarbon cracking in which Ethane (single bonded-Saturated) is “cracked” into Ethyne (double bonded-unsaturated).

Elimination and Addition Reactions

H--C--C--C--C--C--OHH

H

H

H

HH

H H

H

H

***Elimination reactions are also called Dehydration reaction because they UNSATURATE a hydrocarbon and produce water as a second product.***

Pentanol

H2SO4

H3PO4

H--C--C--C--C--CH

H

H

H

HH

H H

H

H

--

Pentene

+ H2O

Elimination and Addition Reactions

H--C--C--C--C--C--HH

H

H

H

HH

Cl H

H

H

***Elimination reaction are also called Dehydration reaction because they UNSATURATE a hydrocarbon and produce water as a second product.***

2- chloropentane

KOHNaOH

+

H--C--C--C--C--C--HH

H

H

H

HH

Cl-H

H

--+ + H2O

Pent-2-ene

Elimination and Addition Reactions

***Addition reaction are also called hydration reactions because they SATURATE a hydrocarbon by adding water as a reactant.***

It is the exact opposite of a hydration reaction. The double or triple bond is broken and the H and OH group are added onto the carbons to keep the 4 bonds rule.

H--C--C--C--HH H

H

H--

Propene

+ HOH H--C--C--C--HH

H

H

H

H

OH

Propan-1-ol

Alcohols and Elimination Reactions

Functional Group: -OH (hydroxyl group)

• Drop the “e” from the end of the alkane, alkene, or alkyne and add -ol

• If necessary add the number of the carbon the –OH group is on; eg., propan-1-ol and propan-2-ol

• If there are more than 1 OH you keep the whole name (KEEP THE “E”) use “di” or “tri” “ol” instead.

Alcohols and Elimination Reactions

Preparation:If you react an alkENE with water (hydration reaction) it will break the double or triple bond and add “H” and “OH”.

H--C--C--C--HH H

H

H--

Propene

+ HOH

Water

H--C--C--C--HH

H

H

H

H

OH

Propan-1-ol

Alcohols and Elimination Reactions

Elimination Reactions:(Dehydrations)• The opposite of an addition (hydration) reaction.

An Alcohol is unsaturated creating a double bond and H2O.

General Formula:Alcohols alkene + Water

R-C—C-ROHH

HH H2SO4

H3PO4

R-C = C-R

HH

+ HOH

Alcohols and Elimination Reactions

Elimination Reactions:(Organic Halide (OH-/Basic)

• The reaction of hydrocarbons containing a halide (F, Cl, Br, I) with an OH- group (basic environment)

General Formula:Organic Halide + OH- Alkene + Halide ion (Cl-) + Water

R-C—C-RClH

HH R-C = C-R

HH

+ HOH

+ Cl-

+ OH-

A functional group consisting of; a double bonded oxygen and OH groups bound to end carbon of a hydrocarbon.

***Can be attached to ANY hydrocarbon chain***Carboxylic acid naming is done the same as a normal hydrocarbon EXCEPT at the end of the hydrocarbon name you add “–oic acid”

Methane Methanoic Acid

Butane Butanoic Acid

A functional group consisting of a single bonded O between TWO carbons and double bonded O.

Named by counting the number of carbons on the =O side and changing the ending to “–oate”.

ethaneethanoateMethyl

You name the second half of the ester (side without =O) like a alkane branch ending in “–yl”

The Ester Functional Group

***Esters are often added to foods for artificial flavours.***

Making an Ester (Esterification)

***An Ester is formed when a carboxylic acid (COOH) reacts with an alcohol (COH) and undergoes a condensation reaction (dehydration).***

Butanoic AcidEthanol

H + OH HOH (Water)

Making an Ester (Esterification)

***An Ester is formed when a carboxylic acid (COOH) reacts with an alcohol (COH) and undergoes a condensation reaction (dehydration).***

butanoateEthy

l

+ H2O

Ester Formation Summary

CH3-C-OH

=O

+ HO-CH3

HOH

CH3-C- + O-CH3 CH3-C-

=

O

O-CH3

ethanoateMethyl

Esterification and Benzene Rings***Esterification when benzene rings have the required carboxylic acid and hydroxyl groups.***

Esterification and Benzene Rings***Esterification when benzene rings have the required carboxylic acid and hydroxyl groups.***

The common plastics around you are formed from single unit monomers linked together into longer chains called polymers.

PolymerMonomerMonomerMonomer

**Addition polymers form from alkene or alkyne monomers.**

Example 1: Polypropene (Propylene)

Propene monomer “sub” units

Again the joining of the monomers breaks the double bonds and connects the monomers together.

General Formula

Example 2: Polyvinyl Chloride

Viny chloride monomer “sub” units

Again the joining of the monomers breaks the double bonds and connects the monomers together.

General Formula

Example 3: Polystyrene

Styrene monomer “sub” units

Again the joining of the monomers breaks the double bonds and connects the monomers together.

General Formula(Styrofoam)

Example 4: Teflon

tetrafluoroethene monomer “sub” units

Again the joining of the monomers breaks the double bonds and connects the monomers together.

General Formula

Condensation polymers are made in a similar way to addition polymers as BOTH polymers are formed from monomer “sub” units.

***BUT, in condensation polymers the “sub” unit are alternating “double ended” carboxylic acids and alcohols forming “ester” linkages.***

OH-C-CH2-CH2-C-OH=

O

=

O

Butane-1,4-dicarboxylic acid

+OH-CH2-CH2-OH

Ethane-1,2-diol

***Just like in esterification, an HOH is removed when they join together***

OH-C-CH2-CH2-C-OH

=

O=

O

Butan-1,4-dicarboxylic acid

+OH-CH2-CH2-OH

Ethan-1,2-diol

HOH

OH-C-CH2-CH2-C-O -CH2-CH2-OH

O

=

-C-CH2-CH2-C-O-CH2-CH2-O-

n

+ HOH

***You ARE NOT expected to be able to name this***

General Formula

O

=

Example 1: Lipids

+ 3 Fatty Acids + 3 HOH

Example 1: Polyester (Synthetic Lipids)

OH-C-CH2-CH2-C-OH

O

=

O=

Butane-1,4-dicarboxylic acid

+OH-CH2-CH2-OH

Ethane-1,2-diol

→-OH-C-CH2-CH2-C-O-

O

=

O

=

CH2-CH2-

n

+ HOH

Example 2: Protein Synthesis( P + P = Amino)

N-CH2-C-OH

O=

(Acids)H

H Glycine(Amino Acid)

No need to memorize

+ N-CH-C-OHH

H CH3

O

=

Alanine(Amino Acid)

→ -N-CH2-C-O-

O

=

HN-CH-C-O-H CH3

O=

Protein Segment

+ HOH

Watern

n

**The bond between two amino acids is called a PEPTIDE bond**

Example 2: Nylon( Synthetic Amino Acids)The same as peptide bonding, EXCEPT no Amino Acids, just alternating “double ended” COOH (carboxylic acid) subunits and “double ended” NH2 (Nitryl) subunits”.

“Double Ended” COOH “Double Ended” NH2

→+ HOH

Watern

n

**The bond between two Nylon molecules is called a AMIDE bond**

Example 2: Kevlar( Synthetic Amino Acids)The same as peptide bonding, EXCEPT no Amino Acids, just alternating “double ended” COOH (carboxylic acid) subunits and “double ended” NH2 (Nitryl) subunits”. AND THERE IS HYDROGEN BONDING BETWEEN POLYMER CHAINS!

OH-C-

O=

-C-OH

O

=

“Double Ended” COOH

+ N- -NH

H

H

H“Double Ended” NH2

→ -C-

O

=

-C-

O

=

N- -N-H H

+ HOH

n

n

Example 2: Kevlar( Synthetic Amino Acids)

-C-

O

=-C-

O

=

N- -NH H

-C-

O

=

-C-

O

=

N- -NH H

-C-

O

=

-C-

O

=

N- -NH H

-C-

O

=

-C-

O

=

N- -NH H

****When multiple polymers line up they hydrogen bond to each other making the polymer even stronger.***