Unit Vocabulary: o Organic Acid o Alcohol. o Ester o Ether. o Amine o Aldehyde

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Unit Vocabulary:

Addition rxn Esterification Polymer

Alcohol Ether Polymerization

Aldehyde Fermentation Primary

Alkane Functional group Saponification

Alkene Halide (halocarbon) Saturated hydrocarbon

Alkyne Hydrocarbon Secondary

Amide Isomer Substitution rxn

Amine Ketone Tertiary

Amino acid Monomer Unsaturated hydrocarbon

Dehydration synthesis Organic acid

Ester Organic chemistry

Unit Objectives:

1. Identify organic compounds versus inorganic compounds based on structure, name, or characteristics of an unknown compound

2. Recognize the characteristics of organic compounds

3. Differentiate between aliphatic, aromatic, saturated, and unsaturated compounds Name organic compounds based on IUPAC rules, with the help of table P and Q 4. Draw organic compounds from a IUPAC name

5. Distinguish between alkynes, alkenes, and alkanes Name and identify isomers

6. Identify various functional groups of organic compounds using Table R:

o Halide (halocarbon) o Organic Acid

o Alcohol o Ester

o Ether o Amine

o Aldehyde o Amide

o Ketone

7. Categorize various organic reactions properly including addition, substitution, polymerization, esterification, fermentation, saponification, and combustion.

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I. Organic Chemistry:

II. Properties of Organic Compounds

A. Mostly nonpolar

B. Solubility: most are INSOLUBLE in water a. LIKE DISSOLVES LIKE

C. Conductivity:

a. mostly NON CONDUCTORS (s), (l), & (aq) states

b. Only ORGANIC ACIDS IONIZE in solution = POOR CONDUCTORS

D. Melting/boiling points:

a. WEAK IMF’s  LOW MP’s/BP’s

E. Reactivity Rate:

a. REACT SLOWLY

i. covalent molecules tend to have relatively HIGH # OF BONDS  MORE STEPS in reaction  rxn takes longer

III. Bonding

A. Carbon has 4 VALENCE ELECTRONS and can form 4 bonds



C

**carbon- always has 4 bonds around it (8 electrons) hydrogen- always has 1 bond around it (2 electrons)

B. These 4 single bonds spread out evenly to create a TETRAHEDRAL molecule (like a tripod)

109.5 degrees, 3-D (on paper, 2- D)

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C. Carbon atoms SHARE ELECTRONS with other carbon atoms, forming COVALENT CHAINS, RINGS, and NETWORKS; Chains of carbon atoms can be open or closed, or even form three-dimensional networks.

D. SATURATED HYDROCARBONS - all SINGLE BONDS between carbons (MAXIMUM number of HYDROGENS attached)

a. When 1 pair of electrons is shared between two carbon atoms the bond is called a single covalent bond.

E. UNSATURATED HYDROCARBONS - at least one MULTIPLE BOND in carbon chain

a. If carbon atoms share two pairs of electrons the bond is called a double covalent bond.

b. Carbons can even share three pairs of electrons. This bond is called a triple covalent bond.

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IV. Types Of Chemical Formulas

A. Molecular Formula: shows the # OF ATOMS of each ELEMENT in a compound;

least informative formula

B. Structural Formula: shows the # OF ATOMS of each ELEMENT AND the ARRANGEMENT of the ATOMS; most informative formula

C. Condensed Formula = COMBINATION of both STRUCTURAL and

MOLECULAR formulas; each carbon is written with its constituent hydrogens followed by the proper subscript

Methane Ethane

Molecular Formula

Structural Formula

Condensed Formula

Ball-and-Stick Model

Space-Filling Model

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V. HOMOLOGOUS SERIES of Hydrocarbons

A. a group of RELATED COMPOUNDS in which each member differs from the one before it by ONE CARBON UNIT

B. Three Groups:

a. Alkanes:

i. hydrocarbons with single covalent bonds

ii. general formula=______________________________

iii. example:

iv. follows IUPAC naming rules-name ends in-__________

v. shows isomerism starting with ____member of the series b. Alkenes:

i. hydrocarbons with double covalent bonds

ii. if you have 2 double bonds, it is called a ____________

iii. general formula=______________________________

iv. example:

v. follows IUPAC naming rules-name ends in-__________

vi. shows isomerism starting with _____ member of the series c. Alkynes:

i. hydrocarbons with triple covalent bonds

ii. general formula=______________________________

iii. example:

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iv. follows IUPAC naming rules-name ends in-__________

v. shows isomerism starting with _____ member of the series

VI. Structural Formula:

A. Straight Chains: also referred to as n-alkanes (“normal” alkanes); n-alkenes, n-alkynes example:

B. Branched: not a straight continuous chain; organic molecule that has smaller branches coming off a longer continuous chain

example:

VII. Nomenclature (IUPAC Naming):

A. Straight Chains of Hydrocarbons

a. prefixes (Table P)-dependent on the number of C's b. suffixes (Table Q)-dependent on the types of bonds

7 B. Branched Hydrocarbons

a. the root name is that of the longest continuous chain of C atoms (aka: main chain) b. any branches off the main chain are called substituents

c. the main chain is numbered so that the substituents receive the lowest possible numbers

i. each substituent receives a name and a number to locate it 1. prefix corresponds to number of carbons (Table P) 2. suffix-always "-yl"

ii. substituents are listed in alphabetical order

iii. when more than one of the same substituent is present use the appropriate prefix (di=two, tri=three)

d. Unsaturated Hydrocarbons

i. the double or triple bond must be included in the main chain.

ii. when numbering with substituents, the bond gets the lowest possible number.

Example 1:

Example 2:

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VIII. Drawing Structural Formulas of Hydrocarbons:

Alkanes:

1. Determine the number of carbons and draw that many in a row

2. Because the molecule name ends in –ane you

know that there are only single bonds. Connect all of the carbons with a single line.

3. Each carbon atom must have 4 bonds connected to it. Add enough hydrogens so that each carbon has 4 total bonds connected to it.

4. Use the molecular formula to make sure that you have the correct number of hydrogens.

Draw the structural formula for propane:

Alkenes:

1. Determine the number of carbons and draw that many in a row connected by a single line.

2. Because the molecule name ends in –ene you

know that there is a double bond. The name of the molecule will tell you where that bond is located. For example, 2-butene will tell you that there are 4 carbons and the double bond is located after the second one. Add another line for the double bond.

3. Each carbon atom must have 4 bonds connected to it. Add enough hydrogens so that each carbon has 4 total bonds connected to it.

4. Use the molecular formula to make sure that you have the correct number of hydrogens.

Example: Pentane

Example: 3-Pentene

9 Draw the structural formula for 4-hexene:

Alkynes

1. follow the same rules as alkenes, except there is a triple bond, not a double bond.

Draw the structural formula for 2-butyne:

IX.Isomers

As the number of carbon atoms increases, the number of possible isomers increases.

The letter n before the name of a hydrocarbon signifies that it is the normal, or straight chain isomer. Branched isomers must have different names.

Naming Isomers: The rules for naming organic compounds are governed by the International Union of Pure and Applied Chemistry (IUPAC).

10 Procedure:

1. Find the longest continuous chain of carbons and use its name as the base. (Example: 4 carbons

= butane)

2. Count the number of carbons in the side branch and assign a prefix based on the name of the corresponding alkane.

(Example: 1 carbon = methane = methyl)

3. If necessary, the location of the side branch (alkyl group) is shown by assigning numbers to the carbons in the longest chain. Numbering should begin at the end that has the side chain attached to the lowest number possible. (Example: 2-methylbutane, not 3-methyl butane)

4. If more than 1 side branch is attached commas are used to

separate the numbers in the name and prefixes are used to denote more than one of the same group, such as 2,2-dimethylbutane:

C - C - C - C

| C C - C - C - C

| C -butane C - C - C - C

| C methylbutane C¹ - C² - C³ - C⁴

| C 2-methylbutane Alkane Alkyl Group

Methane Methyl

Ethane Ethyl

Propane Propyl

11 X. Functional Groups – Table R

Organic compounds in which one or more hydrogen atoms of a hydrocarbon are replaced by other elements

Halocarbons (Halides)

- Organic compounds in which one or more hydrogen atoms are replaced by a halogen (Group 17 element)

- Naming  Same as hydrocarbons, but add a prefix to signify which halogen is attached.

Example:

- 5 carbons, singly bonded = _____________

- Bromine is present on the __st and __th carbons.

- There are __ Bromines.

- Well, the first half would be named 1, 4 – dibromo ________

- The final name is _________________________

Name the following halocarbons:

a. b.

___________________ ___________________

12 Alcohols

- Organic compounds in which one or more hydrogen atoms are replaced by an -OH group. (No more than one OH can be attached to a carbon)

- They are not bases! (Do not form -OH ions in aqueous solution!)

- Naming  Same as hydrocarbons, but drop the “e” ending and add “ol”

(For example: methanol, 2,2-dimethylbutanol. . .)

Primary alcohols

- One –OH group is attached to a carbon on the end of a chain.

- Represented by R-OH, where R is a hydrocarbon chain of any length

Typical example = methanol = CH3OH

1 carbon -OH

Name the following alcohols:

a. CH3CH2OH________________ b. CH3CH2CH2OH______________

Secondary Alcohols:

- One –OH group is attached to a secondary carbon atom. (A carbon attached to 2 other carbons)

13 Tertiary Alcohol:

- One –OH is attached to a tertiary carbon atom. (A carbon attached to 3 other carbons)

* Alcohols can also be classified by the number of hydroxyl groups attached to the carbon chain.

Dihydroxy (2 – OH’s) and Trihidroxy (3 - OH’s) Alcohols contain 2 and 3 hydroxyl groups, just as their names state.

Draw the following molecules:

1. 2-chloro, 2-propanol

2. 2-fluoro, 1,2-butanediol

14 The Carbonyl Group

One of the most functional groups in chemistry, which consists of a carbon atom connected to an oxygen atom by a double bond.

Organic Acids

A family of organic compounds containing the functional group – COOH.

Organic acids are formed by:

1. Dropping the final “e” of the alkane member.

2. Replace the “e” with “- oic” . 3. Then add the word “acid” .

Example: Methane  Methanoic Acid Ethane  Ethanoic Acid

Name this acid:

__________________

15 Aldehydes

- The carbon of the carbonyl group is bonded to at least one hydrogen atom.

- Named by adding the suffix “-al” to the name of the parent hydrocarbon.

Name this aldehyde:

_________________

Ketones

- Has no hydrogen atoms directly attached to the carbonyl group

- Named by adding the suffix “-one” to the name of the parent hydrocarbon.

Name this ketone:

__________________

16 Esters

- Made from an organic acid and an alcohol, resulting in:

- Naming  use the names of the component alcohol and acid and add the suffix -oate.

- Have strong aromas; responsible for the odors of many foods and flavorings

Example: = Methylpropanoate

Ethers

- General formula R1 – O – R2 where each R represents a carbon chain - Commonly named by naming the two branches first and adding the word

“ether”

Example: = diethyl ether

Name this ether:

___________________

Amines

- Formed when 1 or more hydrogens in ammonia (NH3) are replaced by an alkyl group

- Named by changing the –e ending of the alkane name to –amine and adding a number to show the location of the amine group

17 Example: = dimethylamine

Name this amine: ______________________

Amides

- Basically organic acids where the –OH is replaced by an amine group

- Named by changing the –e ending of the alkane name to –amide and adding a number to show the location of the amine group

Example: = ethanamide

Name this amide: ______________________

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XI.Organic Reactions-

COMBUSTION

- When saturated hydrocarbons (like methane) react with oxygen at a high temperature they produce carbon dioxide and water – complete combustion

CH4 + 2O2  CO2 + 2H2O

- If there is insufficient oxygen, carbon monoxide is produced – incomplete combustion.

2CH4 + 3O2  2CO + 4H2O

Write the balanced reaction for the complete combustion of propane:

SUBSTITUTION REACTION

- The replacement of one kind of atom or group by another kind of atom or group.

- An example of this occurs in saturated hydrocarbons where a hydrogen is replaced.

- If the hydrogen is replaced by a halogen (F,Cl, Br, I, At) halogenation is said to have occurred.

Name these compounds: ______________ ________________

19 ADDITION REACTION

- The adding of one or more atoms or groups at a double or triple bond.

- The double or triple bond is changed to a single (saturated) bond or double bond.

- If hydrogen is added, the process is referred to as hydrogenation. This reaction is done on unsaturated hydrocarbons, such as vegetable oils, to make the oils solidify at room temperature: saturated fats tend to be solid at higher temperatures than

unsaturated fats.

Name these compounds: ______________ ________________

ESTERIFICATION

- Organic acids (COOH) react with alcohol’s to produce an ester plus water.

- The process is reversible and slow: Esterification = acid + alcohol  ester + water

- Esterification is also referred to as a hydrolysis (adding water) and is considered to be a dehydration reaction (removing water) or condensation (water product).

Name these compounds:

______________ + ____________  ______________ + water

20 SAPONIFICATION

- The hydrolysis of an ester such as fat with an inorganic base to produce an alcohol and a soap.

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FERMENTATION

- Chemical process where molecules are broken down.

- For example, zymase, an enzyme (which act as catalysts) from yeast, breaks down glucose to form ethanol (the alcohol we drink) and carbon dioxide (carbonation.)

POLYMERIZATION

- A polymer is a large molecule composed of many repeating units called monomers.

- In polymerization, a number of smaller monomers join to form a larger polymer.

- Natural polymers: proteins, cellulose, starch

- Synthetic polymers: polyethylene, nylon and polyester.

21 CONDENSATION POLYMERIZATION

- Monomers are joined by a dehydration reaction of two alcohols whereby water is released and an ester linkage is formed.

- This will continue to grow as additional monomers attach to the dimer.

- Polyester is formed this way.

ADDITION POLYMERIZATION

- Joining of unsaturated monomers to form long chains

- The double or triple bonds are reduced to single or double bonds just like we learned earlier in addition reactions.

- The letter n is used to denote that the monomer unit repeats.