Organic Compounds

Organic Compounds Volatile Organic Compounds (VOCs)

•are a large & diverse family of chemicals that contain carbon and hydrogen •Have a high vapor pressure & easily form vapors at normal temperature & pressure

What are ORGANIC COMPOUNDS? Organic Compounds: Compounds that contain carbon and make up living organisms Carbon is the backbone of life!!!

Organic Compounds •Contain the element carbon, hydrogen and oxygen. •Carbon is found in things that are or once were living. •Carbon atoms share electrons to form covalent bonds.

Organic Compounds •Organic compounds are composed of hundreds to thousands of individual molecules. •The single molecules in a polymer are called monomers.

Organic Compounds

•The long molecules formed by repeating patterns of monomers are called polymers.

Molecular Low melting points Low boiling points Low Hf Low Hv High evaporation rate High vapor pressure May be gases, liquids, or solids

Decompose on heating Poor conductors of heat & electricity Nonpolar (vdw forces) Dissolve in nonpolar solvents React slowly Solids may be soft or brittle

Properties of hydrocarbon molecules

Why is carbon the backbone of life? Why is it special?

1. Carbon has 4 electrons in its outer shell. To satisfy the octet rule, it needs to share 4 other electrons. 2. This means that each carbon atom forms 4 bonds

Organic compounds may be NATURAL or SYNTHETIC

What are the different types of Carbon Molecules?

Three Types Of Carbon Molecules 1. Straight Chain:

2. Ring:

3. Branched Chain:

How do we classify ORGANIC COMPOUNDS?

are classified by FUNCTIONAL GROUP a structural unit in a molecule responsible for its characteristic chemical behavior and its spectroscopic characteristics

Hydrocarbons

Aliphatic

Aromatic

Hydrocarbons

• Contains only two elements (carbon & hydrogen) • Simplest class of organic compounds • Formed by bonds depending on the arrangement of its valence electrons (hybridization)

Aliphatic vs Aromatic •Aliphatic hydrocarbons are the organic molecules containing Carbon (C) and Hydrogen (H) atoms in their structure; in straight chains, branched chains •Aromatic hydrocarbons are sometimes known as “arenes” or “aryl hydrocarbons”, contain a benzene ring in their structure

octane

5-ethyl-3-methyloctane

as HYDROCARBONS • Alkane • Alkene • Alkyne • Cycloalkane • Aromatic hydrocarbon • Alkyl halide

a l i p h a t i c

a r o m a t i c

as compounds containing OXYGEN • Alcohol • Ether • Aldehyde • Ketone • Carboxylic acid • Ester

as compounds containing NITROGEN • Amine • Amide

What are FUNCTIONAL GROUPS?

Functional groups are specific groups of atoms within molecules that have very characteristic properties regardless of the other atoms present in a molecule.

responsible for the characteristic chemical reactions of those molecules. ...

Note: The atoms of functional groups are linked to each other and to the rest of the molecule by covalent bonds.

How (where) can we use these organic compounds?

Applications of Organic Chemistry • Medicine ( antibiotics, anticancer drugs, painkillers, anti-depressant, anaesthetics etc.)

• Drugs to cure, diagnose & study disease • Food • Cleansing agents • Sterilizing agents • Analytic substance • Valuables

Steps in WRITING & NAMING ORGANIC COMPOUNDS

Ways of Expressing Organic Compounds

• Molecular Formula [C8H18] • Condensed Structural Formula [CH3CH2CH2CH2CH2CH2CH2CH3] • Line Bond Structural Formula • Skeletal Formula

IUPAC Rules for Naming Hydrocarbons 1. Choose the correct ending:

“-ane”, “-ene”, or “–yne” 2. Determine the longest carbon chain. Where a double or triple bond is present, choose the longest chain that includes this bond. If there is a cyclic structure present, the longest chain starts and stops within the cyclic structure.

3. Assign numbers to each C of the parent chain. For alkenes and alkynes the first carbon of the multiple bond should have the smallest number. For alkanes the first branch (or first point of difference) should have the lowest #. Carbons in a multiple bond must be numbered consecutively. 4. Attach a prefix that corresponds to the number of carbons in the parent chain. Add cyclo- to the prefix if it is a cyclic structure.

5. Determine the correct name for each branch (“alkyl” groups include methyl, ethyl, propyl, etc.) 6. Attach the name of the branches alphabetically,) along with their carbon position, to the front of the parent chain name. Separate numbers from letters with hyphens (e.g. 4-ethyl-2-methyldecane)

7. When two or more branches are identical, use prefixes (di-, tri-, etc.) (e.g. 2,4-dimethylhexane).

Numbers are separated with commas. Prefixes are ignored when determining alphabetical order. (e.g. 2,3,5-trimethyl-4-propylheptane) 8. When identical groups are on the same carbon, repeat the number of this carbon in the name. (e.g. 2,2-dimethylhexane)

Naming Side Chains

CH2 CH3 CH2 C

CH2 CH3 CH2 C

CH3

CH3 Rule 1: choose the correct ending ene

Naming Side Chains

CH2 CH3 CH2 C

CH2 CH3 CH2 C

CH3

CH3

Rule 2: determine the longest carbon chain ene

Naming Side Chains

CH2 CH3 CH2 C

CH2 CH3 CH2 C

CH3

CH3

Rule 3: Assign numbers to each carbon ene

Naming Side Chains

CH2

CH2 CH3

1

CH3 CH2 C

2

5

CH2 C 3

4

6

CH3

CH3

Rule 3: Assign numbers to each carbon ene

Naming Side Chains

CH2

CH2 CH3

1

CH3 CH2 C

2

5

CH2 C 3

4

6

CH3

CH3

Rule 4: attach prefix (according to # of Cs) 1-hexene ene

Naming Side Chains

ethyl

CH2

CH2 CH3

1

CH3 CH2 C

2

5

CH2 C 3

4

CH3

6

CH3

methyl

methyl

Rule 5: Determine name for side chains 1-hexene

Naming Side Chains

CH2

ethyl

CH2 CH3

1

CH3 CH2 C

2

5

CH2 C 3

4

CH3

6

CH3

methyl

methyl

Rule 6: attach name of branches alphabetically

2-ethyl-4-methyl-4-methyl-1-hexene 1-hexene

Naming Side Chains

CH2

ethyl

CH2 CH3

1

CH3 CH2 C

2

5

CH2 C 3

4

CH3

6

CH3

methyl

methyl

Rule 7,8: group similar branches 2-ethyl-4-methyl-4-methyl-1-hexene 1-hexene

Naming Side Chains

CH2

ethyl

CH2 CH3

1

CH3 CH2 C

2

5

CH2 C 3

4

CH3

6

CH3

methyl

methyl

Rule 7,8: group similar branches

2-ethyl-4,4-dimethyl-1-hexene

CH3 CH

CH2

CH3

propene

CH3 CH

CH3

CH

CH3 CH

C

CH3

CH CH3 2,4-dimethyl-2-pentene

2-butene

CH

C

CH2 CH3

1-butyne

CH3 CH2 CH

C

CH3

CH2 CH3

CH3

CH3

C

CH

CH2

CH3

b) same

CH3 C

CH

CH2

a) 3,3-dimethyl-1-pentene

CH3

C

CH3 CH

CH2

CH2 CH3

c) 5-ethyl-4-methyl-2-heptyne

Counting the carbon atoms code

meth eth prop but pent hex

no of carbons 1 2 3 4 5 6

Types of carbon-carbon bonds

code

means

an

only carbon-carbon single bonds

en

contains a carbon-carbon double bond

#1. CHECK how many Carbon atoms are in the chain

#2. REFER at the table to determine what its name is.

#3. INSPECT if it has a double bond. REPLACE the -ane with an -ene. For example this would be Ethene

#4. Examine the Haloalkane! (halo- HALOGEN)

#5. COUNT the Number of CARBONS, starting from the Halogen (or functional group).

#6. NAME the COMPOUND !

#7. CHECK on the PRESENCE of FUNCTIONAL GROUPS!

#8. NAME IT ! To name it, make sure to count from the side that gives it the smallest number. (In this case it can only be 2)

2 – Methyl Propane

TRY THIS

#9a. TWO HALOGENS into a HYDROCARBON! (COUNT OUT on which number carbon the HALOGENS are attached to, remembering to keep the lowest numbered carbons)

#9b. TWO HALOGENS into a HYDROCARBON! (Get the Halogens in ALPHABETICAL ORDER. Example: Bromo comes before Chloro. Use this information here is for the name of this molecule.)

TRY THIS !

How to deal with ALKANES? A. FIND THE PARENT HYDROCARBON Find the longest continuous chain of carbon atoms. If two different chains of equal length are present, choose the larger of branch points as the parent. B. NUMBER THE ATOMS IN THE MAIN CHAIN Beginning at the end nearer the first branch point, number each carbon atom in the parent chain. If there is branching and equal distance away from both ends of the parent chain, begin numbering at the end nearer the second branch point .

C. IDENTIFY AND NUMBER THE SUBSTITUENTS. Assign a number to each substitute according to its point of attachment to the parent chain. If there are two substituents on the same carbon, give them both the same number. There must be as many numbers in the name as there are substituents . D. WRITE THE NAME AS A SINGLE WORD Use Hyphens to separate the different prefixes, and commas to separate numbers. Cite them in alphabetical order if two or more substituents are present. If two or more identical substituents are present use one of the multiplier prefixes DI-,TRI-, TETRA-, and so forth.

E. NAME A COMPLEX SUBSTITUENT AS THOUGH IT WERE ITSELF A COMPOUND First name the complex substituent. Begin numbering the complex substituent at the point of attachment to the main chain, and identify it as a 2 methylpropyl group.

Practice Exercise 1

 Get your show board  Use your guide (index card)

2 – methyl propane

2 – methyl butane

4 – ethyl heptane

3-ethyl-4-methyl heptane

5-ethyl-3-methyl octane

Answer the following: A. GIVE THE NAME OF THE FF.:

Answer the following: B. DRAW THE STRUCTURAL FORMULA OF THE FF.: 1. 4 – ethyl octane 2. 2 – methyl nonane 3. 2 – methyl – 2 – ethyl butane 4. 3 – ethyl pentane 5. 2 – methyl – 3 – ethyl pentane

How to deal with ALKENES?

A. Name the parent hydrocarbon by locating the longest carbon chain that contains the double bond and name it according to the number of carbons with the suffix -ene. When there is more than one multiple bond, use numerical prefixes (diene, diyne, triene, etc.) B. Number the Carbon Atoms in the main chain. Begin at the end nearer the multiple bond. If the multiple bond is at the same distance from both ends, begin numbering at the end nearer the first branch point.

C. Write the full name Assign numbers to the branching substituents, and list the substituents alphabetically. Indicate the position of the multiple bond(s) in the chain by giving the number of the first multiple bonded carbon. If more than one multiple bond is present, identify the position of each multiple bond and use the appropriate ending diene, triene, tetraene, and so forth.

Practice Exercise 2

 Get your show board  Use your guide (index card)

Answer the following:

A. GIVE THE NAME OF THE FF.:

B. DRAW THE STRUCTURAL FORMULA OF THE FF.: 1. 2-ethyl-1-pentene 2. 2,3-dimethyl-1-butene 3. 2,3,4 – trimethyl-1-hexene