CH.19 - ORGANIC CHEMISTRY: FUELS, PHARMACEUTICALS, AND...

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CHEMISTRY - KIRSS 2E

CH.19 - ORGANIC CHEMISTRY: FUELS, PHARMACEUTICALS, AND MODERN MATERIALS

TOPIC: ORGANIC CHEMISTRY

Organic Chemistry is the study of carbon and the other common nonmetals it is connected to:

____ , ____ , ____ & ____ .

Some organic molecules are made of just carbons and hydrogens and are aptly named _____________________.

C

H

H

H

C

H

H

C

H

H

H

A B

CC

CC

O

H

H

H H H

H

H

H

C

H

H

H

N H

H

C D

H – Cl



TOPIC: STRUCTURAL FORMULAS

Your typical organic molecule can be drawn in a few different ways.

For example if you take a look at pentane, C5H12.

C

H

H

H

C C C C

H

H

H

H

H

H

H

H

H

Structural Formula Condensed Formula

CH3–CH2–CH2–CH2–CH3

Skeletal Formula

EXAMPLE 1: Determine the molecular formula for the following organic compound.

EXAMPLE 2: Convert the following structural formula into its condensed formula.

C

H

H

H

C C C C

H

H

CH3

H

H

H

C

H

H

H



PRACTICE: STRUCTURAL FORMULAS 1



HN

NH

O

O

Uracil (U) RNA

EXAMPLE 3: Convert the following structural formula into the carbon skeleton formula, otherwise known as a kekulé

structure.

C

O

HO C O C C

H

H

C

H

N

H H

H

H

H

H

H



TOPIC: CHIRALITY

A molecule is chiral when it possesses a carbon that has ________ unique groups attached to it.

This molecule is said to be non-superimposable.

The mirror image of any chiral molecule is called an _____________________ and together they

are referred to as ____________ isomers or _____________ isomers.

Br

C

HOCH3

H

mirror

Br

C

OHH3C

H

EXAMPLE 1: Identify the compound that possesses an asymmetric center.

Cl C

H

H

H

A B C D

C C

CH3

C

CH3

HO–CH2 H C C

F

H

H

H

Cl

H

H3C

Cl



PRACTICE: CHIRALITY 1

EXAMPLE 1: From the previous question draw the mirror image of the chiral molecule.

EXAMPLE 2: Draw the mirror images for the following molecule.

Mirror Method Inversion Method

OHCl

PRACTICE: Draw the mirror images for the following molecule.

Mirror Method Inversion Method



TOPIC: OPTICAL ACTIVITY

We recently learned that a chiral molecule is one that possesses a carbon connected to four distinct groups.

One key feature of chiral molecules is that they rotate plane polarized light.

Clockwise rotation = dextrorotatory (d) or (+) Counterclockwise rotation = levorotatory (l) or (–)

Chiral Solution

Chiral Solution

The names and degrees of rotation have nothing to do with the chirality of the compounds.

EXAMPLE: Which of the following compounds would be optically active?

A B C D

Cl

Br

OHF



TOPIC: HYDROCARBONS

The term of “hydrocarbon” refers to compounds that contain only carbons and hydrogens. These compounds may

possess single, double or triple bonds.

Carbons are ___________________ meaning that when they are neutral they must make 4 bonds.

C

H

H

H

C

H

H

H

Alkane

C

H

H

C

H

H

Alkene

CH C H

Alkyne

C

CC

C

CC

H

H

H

H

H

H

Benzene

Alkane Prefixes The name of alkanes is based on the number of carbons in the compound. These alkane “prefixes” must be

memorized in order to name more complex structures later on in the chapter.

# of Carbons

Alkane Prefix # of

Carbons

Alkane Prefix

1

6

2

7

3

8

4

9

5

10



Alkanes Alkanes are hydrocarbons that contain only single bonds. They are sometimes referred to simply as “ saturated”

hydrocarbons.

Since all of the carbons are connected to 4 electron groups they all have an _______ hybridization.

Alkanes have a generic formula of _____________.

C

H

H

H

C

H

H

C

Propane

C

H

H

H

C

H

H

H

Ethane

H

H

H

EXAMPLE 1: Determine the formula and name of a hydrocarbon that contains only single bonds and 8 carbons. There is a direct relationship between an alkane’s weight and it’s measured boiling point.

Generally, the _____________ the molecular weight of an alkane the higher its boiling point.

Number of Carbons Physical State Usage

Up to 4

Gas

Cooking and Heating

5 to 7

Volatile Liquids

Gasoline and solvents

6 to 18

Liquids

Gasoline

12 to 24

Liquids

Jet Fuel

16 to 50

High Boiling Liquids

Diesel, heating oils and grease

Over 50

Solids

Petroleum jelly, waxes



Alkenes Alkenes are hydrocarbons that contain at least one double bond. They are sometimes referred to simply as

“unsaturated” hydrocarbons.

The double bonded carbons are connected to 3 electron groups and so have an _______ hybridization.

Alkenes and cycloalkanes have a generic formula of _____________.

CH

H

C

H

C

Propene

C

H

H

C

H

H

Ethene

H

H

H

Cyclohexane

EXAMPLE 2: Determine the formula and simplest name of a hydrocarbon that contains one double bond and 6 carbons.



Alkynes Alkynes are hydrocarbons that contain at least one triple bond. They are sometimes referred to simply as

“unsaturated” hydrocarbons just like the alkenes.

The triple bonded carbons are connected to 2 electron groups and so have an _______ hybridization.

Alkynes have a generic formula of _____________.

CH C C

Propyne

CH C H

Ethyne

H

H

H

EXAMPLE 3: Determine the formula and simplest name of a hydrocarbon that contains one triple bond and 9 carbons.



Aromatics Aromatic compounds have a benzene ring (C6H6) as their major defining feature.

C

CC

C

CC H

H

H

H

H

H

C

CC

C

CC H

H

H

H

H

H

Resonance Structures

C

CC

C

CC H

H

H

H

H

H

Resonance Hybrid

Benzene rings can be found in many everyday compounds from fossil fuels to even some vital medications.



TOPIC: ALKYL GROUPS

The removal of a hydrogen atom from an alkane compound creates an alkyl group. Remembering these alkyl groups

are the first step in learning how to name organic compounds.

H C

H

H

H

Methane

C

H

H

H

Methyl

When you have a two carbon chain then the alkyl name will be ______________.

CH3 – CH3

________________

CH2CH3

________________



When you have a three carbon chain then the alkyl name will be __________________ or __________________.

________________

CH3–CH2–CH3

________________

CH2CH2CH3 CH3CHCH3

________________

When you have four carbons then the alkyl names will be ____________________ , ____________________ ,

_____________________ or _____________________ .

________________

CH3–CH2–CH2–CH3

________________

CH2CH2CH2CH3 CH3CHCH2CH3

________________



________________

CH3–CH–CH3

________________ ________________

CH3

CH2–CH–CH3

CH3 CH3–C

CH3

CH3

EXAMPLE: Based on your knowledge of chemical structures draw the three isomers of C5H12 (pentane).



TOPIC: NAMING ALKANES When naming any alkane compound there is a set of rules you should follow to get the correct answer.

1. Find the longest carbon chain and assign a root name accordingly.

If there is a tie between longest chains, choose the chain that gives _____________ substituents.

Substituents are the groups that branch off the main chain and weren’t counted as part of the main chain.

2. Number the chain from the end closest to a substituent.

3. Substituents will be named alphabetically and a number will accompany the location of their attachment.

4. If more than one of a similar alkyl group is present then we must use numerical prefixes to describe the

number of them.

__________ – 2 __________ – 3 __________ – 4 __________ – 5



PRACTICE: NAMING ALKANES 1

EXAMPLE 1: Naming the following alkane compound.

a) EXAMPLE 2: Naming the following alkane compound.

b) EXAMPLE 3: Naming the following alkane compound.

c )



PRACTICE: NAMING ALKANES 2

EXAMPLE 4: Determine the structure for the following alkane compound.

3, 4, 5-trimethyldecane


4-tert-butyloctane


1-bromo-2,3-dichlorocycloheptane



TOPIC: NAMING ALKENES Naming an alkene is similar to naming an alkane with a few differences.

1. Find the longest carbon chain and change the “ane” ending to “ene”.


2. Number the chain from the end closest to the double bond and provide a number for its location.



number of them.

__________ – 2 __________ – 3 __________ – 4 __________ – 5

EXAMPLE 1: Naming the following alkene compound.



PRACTICE: NAMING ALKENES 1 EXAMPLE 2: Naming the following alkene compound.

EXAMPLE 3: Determine the structure for the following alkene compound.

5-bromo-4,4-dimethyl-2-heptene EXAMPLE 4: Determine the structure for the following alkene compound.

2, 5–octadiene EXAMPLE 5: Determine the structure for the following alkene compound.

Trans–3–hexene



TOPIC: NAMING ALKYNES Naming an alkyne is similar to naming an alkane with a few differences.

1. Find the longest carbon chain and change the “ane” ending to “yne”.


2. Number the chain from the end closest to the triple bond and provide a number for its location.



number of them.

__________ – 2 __________ – 3 __________ – 4 __________ – 5

EXAMPLE 1: Naming the following alkyne compound.

EXAMPLE 2: Provide the structural formula from the following alkyne name. 4–phenyl–2–nonyne



TOPIC: ALKANE REACTIONS Alkanes are also referred to as _______________, which is derived from Latin meaning “little affinity”.

This explains their very low reactivity.

Alkanes in general undergo only two main types of reactions.

a) _______________________________

b) _______________________________



TOPIC: FREE RADICAL CHAIN REACTION

As previously stated, alkanes are almost completely unreactive.

And one of the two reactions it undergoes is free-radical halogenation.

Under this reaction a ________________ on a carbon is replaced by a ________________.

The Radical Chain Reaction

Alkanes will react with diatomic halogens in the presence of __________________________________.

Initiation: (A stable compound undergoes homolytic cleavage: 0 free radicals 2 free radicals)

Propagation: (The radical reacts with a stable compound to create a new radical and new stable compound.)

Termination: (Two radicals join to create a stable compound: 2 free radicals 0 free radicals)



PRACTICE: FREE RADICAL CHAIN REACTION 1

EXAMPLE 1: Determine the major product(s) of the following reaction.

CH3CH3 + Br2

Heat or Light

EXAMPLE 2: Determine the major product(s) of the following reaction.

CH3CH2CH3 + Cl2Heat or Light



TOPIC: HALOGENATION

Alkenes and alkynes undergo addition reactions in which elements add across their ______

bonds to create new ______ bonds.

• Under Halogenation, ______ halogens are added to ______ pi bond.

EXAMPLE 1: Determine the major product from the following Halogenation reaction.

EXAMPLE 2: Determine the major product from the following Halogenation reaction.

CH3CH=CH2 + Cl2

+ 2 moles Br2



TOPIC: HYDROGENATION

Hydrogenation can be seen as a reduction reaction in which _____ hydrogens are added to _____ pi bond.

• In General Chemistry reduction is gaining _________ , but in Organic Chemistry

reduction is thought of as gaining ________________.

EXAMPLE 1: Determine the major product from the following Hydrogenation reaction.

EXAMPLE 2: How many moles of hydrogen would be needed to completely reduce the

following compound?

+ H2Catalyst

C CH

CH3

C

CH3



TOPIC: HYDROHALOGENATION

Under Hydrohalogenation, a _________________ and a _________________ are added across a pi bond.

1) Follows Markovnikov’s Rule

a) Hydrogen goes to the double bonded carbon with _______ hydrogens.

b) Halogen goes to the double bonded carbon with _______ hydrogens.

EXAMPLE 1: Determine the major product from the following Hydrohalogenation reaction.

EXAMPLE 2: Determine the major product from the following Hydrohalogenation reaction.

C CH

CH3

CH2CH2CH3

CH2CH3+ HCl

+ 2 moles HBrH3C C CH



TOPIC: AROMATIC REACTIONS Although benzene rings have pi bonds like alkenes and alkynes, they cannot undergo addition reactions because they are much too stable.

• We often refer to benzene as an aromatic compound in order to describe its high level of stability.

Instead of doing addition reactions benzene rings will under ________________ reactions in order to

maintain their aromaticity. The two major types of Aromatic reactions we will investigate will be:

1. _______________________________ – where a halogen is placed on benzene.

H

H

H

H

H

H

FeBr3+ Br2

H

H

H

H

H

H

FeCl3+ Cl2



2. _______________________________ – where an alkyl group is placed on benzene.

H

H

H

H

H

H

AlCl3+ CH3Cl

EXAMPLE 1: Determine the major product from the following Aromatic reaction.

H

H

H

H

H

H

AlBr3+Br



TOPIC: NOMENCLATURE OF FUNCTIONAL GROUPS Naming a compound with a functional group is similar to previous examples of naming we’ve done.

1. Find the longest carbon chain and change the “ane” ending based on the functional group present.

• If there is a tie between longest chains, choose the chain that gives _____________ substituents.

2. Number the chain from the end closest to the functional group present and provide a number for its location.

• Some functional groups don’t need their location numbered because they are terminal.


4. If more than one of a similar alkyl group is present then we must use numerical prefixes to describe the number

of them. __________ – 2 __________ – 3 __________ – 4 __________ – 5

Class Suffix Name Carboxylic Acid

-oic acid

Ester

-oate

Aldehyde

-al

Ketone

-one

Alcohol

-ol

Amine

-amine

Alkene

-ene

Alkyne

-yne

Alkane

-ane

Ether

ether

Alkyl Halide

---



PRACTICE: NOMENCLATURE OF FUNCTIONAL GROUPS 1 EXAMPLE 1: Provide the name of the following alcohols and alkyl halides and state if they are primary, secondary or tertiary.

a) BrCH2CH2CH2OH b)

CH3CH2CH2CH2CCH3

CH2CH3

OH

c) CH3CH2CH2CHCH3

Cl

EXAMPLE 2: Provide the name of the following functionalized organic compounds.

a) CH3COH

O

b) CH3CH2CH2CH2CH

O

c) CH3CH2CH2CH2CCH2CH3

O



PRACTICE: NOMENCLATURE OF FUNCTIONAL GROUPS 2

EXAMPLE 3: Provide the name of the following functionalized organic compound.

EXAMPLE 4: Provide the name of the following amines and state if they are primary, secondary or tertiary.

a) CH3CH2CH2CHCH2CH3

NH2

b) CH3CH2CH2NHCH2CH3

EXAMPLE 5: Provide the name of the following ethers

a) CH3CH2CH2OCH3 b) CH3CH2OCH2CH3



PRACTICE: NOMENCLATURE OF FUNCTIONAL GROUPS 3

EXAMPLE 6: Provide the structure of the following aromatic hydrocarbons. p-ethyltoluene EXAMPLE 7: Provide the structure of the following aromatic hydrocarbons. m-bromobenzoic acid EXAMPLE 8: Provide the structure of the following aromatic hydrocarbons. 2,4,6-trimethylnitrobenzene



TOPIC: ALCOHOL REACTIONS

Alcohols can be easily identified by the presence of the hydroxyl group ________ .

• Because of the presence of this highly polarized group alcohols can be involved in many organic reactions.

1. Substitution Reactions – under this reaction alcohols react with the hydrohalic acids of ______ or ______ to become alkyl halides.

CH3CH2CHCH2CH2CH3

OH

+ HBr

2. Elimination Reactions – under this reaction under the presence of concentrated acids such as __________ or __________ an alcohol undergoes dehydration to form an alkene.

CH3CCH3

OH

+ H2SO4

CH3



3. Oxidation Reactions – An alcohol can be seen as an alkane that has undergone an initial oxidation. The alcohol

can then continue to be oxidized to form either a(n) _________________ or _________________.

• This is done with the strong oxidizing agent sodium dichromate, Na2Cr2O7 and the strong acid sulfuric acid,

H2SO4.

• There is also an inverse relationship that can change our products back into their reactants.

CH3CCH3

OH

CH3

CH3CH2CHCH3

OH

CH3CH2CH2 OH H2SO4

Na2Cr2O7

H2SO4

Na2Cr2O7

H2SO4

Na2Cr2O7



TOPIC: CARBOXYLIC ACID DERIVATIVE REACTIONS Esters and amines are involved in reactions that deal with carboxylic acids.

1. Esterification – Under this reaction a carboxylic acid reacts with an alcohol and undergoes a dehydration reaction

in order to form an ester.

+ CH3CH2CH2OHHeatC

O

OH

2. Amide Formation – Under this reaction a carboxylic acid reacts with an amine and undergoes a dehydration to

reaction in order to form an amide.

+ CH3CH2NHCH3Heat

CH3CH2C

O

OH



CH.19 - ORGANIC CHEMISTRY: FUELS, PHARMACEUTICALS, AND...

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Transcript of CH.19 - ORGANIC CHEMISTRY: FUELS, PHARMACEUTICALS, AND...