Organic Chemistry

Name ______________________________________________

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Content Objectives:

1. Draw structural formulas for alkanes, alkenes, and alkynes containing a maximum of 10 carbon atoms

2. Classify an organic compound based on its structural or condensed structural formula3. Draw a structural formula with the functional group(s), on the straight chain hydrocarbon, when

given the correct IUPAC name for the compound4. Identify types of organic reactions5. Determine a missing reactant or product in a balanced equation6. Make real world connections to: odors (esters), saponification-making soap, polymerization-

formation of starches, fermentation-alcohol production, combustion of fossil fuelsKey Subject Competencies

1. Explain how bonding occurs between carbon atoms2. Determine common characteristics of the Alkane family 3. Distinguish among the different families of hydrocarbons4. Determine common characteristics of the families5. Use table Q to identify different families of hydrocarbons6. Use table P to name the members of the different families of hydrocarbon compounds7. Identify unsaturated organic compounds by the fact that these compounds have double or triple

bonds between carbon atoms in a chain8. Determine the name aliphatic hydrocarbons9. Name the alkyl radicals10. Name halogen side chains11. Use Table R to identify the functional groups for halides, alcohols, ethers, and aldehydes12. Use Table R to determine the names of different draw ketones, organic acids, esters, amines,

and amides? 13. Identify isomers as molecules that have the same molecular formulas but different structural

formulas14. Explain why isomers of molecules have different properties15. Describe and distinguish between substitution and addition reactions16. Distinguish between substitution and addition reactions when given samples of each17. Describe and recognize a polymerization reaction18. List some natural polymers and synthetic polymers19. Recognize and distinguish between esterification, fermentation, saponification,and combustion

Vocabulary:

Addition reactionAlcoholAldehydeAlkaneAlkeneAlkyneAmideAmine

Amino acidEsterificationEsterEtherFermentationFunctional groupHydrocarbonIsomer

KetoneOrganic acidOrganic halidePolymerPolymerizationSaponificationSaturated/UnsaturatedSubstitution reaction

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What is meant by the term Organic?

Characteristics of organic compounds Formed as a result almost exclusively of _____________________ bonding

Generally ______________________ \ Generally insoluble in watero usually soluble in nonpolar solvents (other organic compounds)

Non-electrolytes ___________________________________ which are weak electrolytes

Have low melting points (due to _______________________________________ forces)o The great number of carbons leads to a higher melting point.

Have slower reaction rates than inorganic compoundso covalent bonds within organic molecules are strongo activation energies are higho catalysts are often used to increase reaction rates

How can we describe Hydrocarbons? Hydrocarbons

o Definition - compounds composed of only _______________________________o There are so many hydrocarbons found in nature; nearly impossible to study all!

They are grouped in ____________________________ series.o Homologous series - group of organic compounds with similar properties and

related structures (differ from each other by CH3)o

3 Important Homologous Series of Hydrocarbons:

_______________________________

_______________________________

_______________________________

Aliphatic - hydrocarbon chainso Saturated - has no bonds that can be broken to add extra hydrogeno Alkanes

family of hydrocarbons with all single bonds general formula CnH2n+2 named with suffix "ANE“ Table P – Organic Prefixes As the number of carbons increases, the boiling point increases.

Name and draw the first ten Alkaneso Go to table P and look at the prefix for the number of carbons

1 carbon is Meth - All alkanes end in ‘ane’ - methaneTAKE OUT PAPER AND DRAW PLEASE

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What are the Unsaturated Hydrocarbons? Unsaturated - has double or triple bonds that can be broken to add more hydrogen

o Alkenes family of hydrocarbons with at least one double bond general formula CnH2n named with suffix "ENE“ Starts with Ethene.

Draw the first nine Alkenes - TAKE OUT PAPER AND DRAW PLEASEo Go to table P and look at the prefix for the number of carbons

2 carbons is Eth - All alkenes end in ‘ene’ - etheneo Alkynes

family of hydrocarbons with one triple bond general formula CnH2n-2 named with suffix "YNE“ Starts with Ethyne.

Draw the first nine Alkynes - TAKE OUT PAPER AND DRAW PLEASEo Go to table P and look at the prefix for the number of carbons

2 carbons is Eth - All alkenes end in ‘yne’ - ethyne

With this ring I, get confused? The Benzene Series

(Aromatic hydrocarbons)o The benzene series consists of molecules which are cyclic in nature.o The general formula is CnH2n-6.

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Practice Time

1) Which is the structural formula of ethene?

a.

b.

c.

d.

2) Hydrocarbons are compounds that containa. carbon, onlyb. carbon and hydrogen, onlyc. carbon, hydrogen, and oxygen, onlyd. carbon, hydrogen, oxygen, and nitrogen, only

3) Which formula represents an unsaturated hydrocarbon?a. C2H6

b. C3H8

c. C5H8

d. C6H14

4) Which formula represents an unsaturated hydrocarbon?a. CH2CHClb. CH3CH2Clc. CH3CH2CH3

d. CH3CHCH2

5) Which compound is a saturated hydrocarbon?a. CH2CH2

b. CH3CH3

c. CH3CHOd. CH3CH2OH

6) Which element is present in every organic compound?a. carbonb. fluorinec. nitrogend. oxygen

7) Which element has atoms that can bond with each other to form long chains or rings?a. carbonb. nitrogenc. oxygend. fluorine

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8) Which structural formula represents a member of the series of hydrocarbons having the general formula CnH2n-2?

a.

b.

c.

d.

9) Which compound is an alkyne?a. C2H2

b. C2H4

c. C4H8

d. C4H10

10) The compound C4H10 belongs to the series of hydrocarbons with the general formulaa. CnH2n

b. CnH2n+2

c. CnH2n-2

d. CnH2n-6

11) Which formula represents propyne?a. C3H4

b. C3H6

c. C5H8

d. C5H10

12) A carbon-carbon triple bond is found in a molecule ofa. butaneb. butanonec. butened. butyne

13) A molecule of a compound contains a total of 10 hydrogen atoms and has the general formula CnH2n+2. Which prefix is used in the name of this compound?

a. but-b. dec-c. oct-d. pent-

14) Which formula represents a saturated hydrocarbon?a. C2H2

b. C2H4

c. C3H4

d. C3H8

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15) Which structural formula represents 2-pentyne?

a.

b.

c.

d.

16) Which structural formula correctly represents a hydrocarbon molecule?

a.

b.

c.

d.

17) Which general formula represents the homologous series of hydrocarbons that includes the compound 1-heptyne?

a. CnH2n-6

b. CnH 2n-2

c. CnH2n

d. CnH2n+2

18) A double carbon-carbon bond is found in a molecule ofa. pentaneb. pentenec. pentyned. pentanol

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19) Which structural formula represents an unsaturated hydrocarbon?

a.

b.

c.

d.

20) Given the structural formula:

What is the IUPAC name of this compound?a. propaneb. propenec. propanoned. propanal

21) Which hydrocarbon is saturated?a. propeneb. ethynec. butened. heptanes

22) Which hydrocarbon is a member of the alkane series?

a.

b.

c.

d.

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23) Which compound is a member of the same homologous series as C3H8?a. CH4

b. C4H8

c. C5H8

d. C5H10

24) Which is a saturated hydrocarbon?a. etheneb. ethynec. propened. propane

How can we name organic compounds?

Rule 1: Find the longest continuous chain Rule 2: Assign numbers to each C atom in the longest chain, starting at the end with the

attached group. Rule 3: If more than one of the same types of group is attached to the main chain

prefixes are used to identify the attached groups. Rule 4: When naming alkenes or alkynes the carbon with the double/triple bond, the

carbon number with the double/triple bond must be identified in the name.

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CH2 ─ CH3

|a) CH3─ CH ─CH2─CH ─ CH ─ CH3

| | CH2 CH3

| CH3

CH3 Hb) \ /

C = C / \ H CH2 ─CH3

c) CH ≡ C─ CH3

d) CH3 -CH2-CH2-CH=CH-CH3

e) CH2=CH-CH2-CH=CH-CH3

f) CH3 – CH2 - C ≡ C- CH2- CH3

How can we represent organic compounds?o Molecular Formula

Shows the kind and number of atoms in a compound. Example: CH4 or C2H6 Tells us that there are carbon and hydrogen atoms. For methane, there are

4 hydrogens for 1 carbon atom.o Structural Formula

In addition, shows the bonding patterns and two-dimensional view. For example:

o Condensed Structural Formula Written structural formula For example: Methane: CH4 Ethane: CH3CH3

o Ball-and-Stick Model Shows a 3D structure of the compound

o Space-Filling Model Shows the actual structure of the compound

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Isomerso When a molecular formula can be represented by more than one structural

arrangemento Isomers have the same molecular formula, but different physical and chemical

properties.o As the # of carbon atoms increases, so does the # of possible isomers

How would you draw the structural formula for a 4 carbon hydrocarbon?

Isomer Practiceo Draw 3 Isomers for 5 and 6 carbon Alkanes.o Be sure you have the correct number of hydrogens.

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1. Given a formula representing a compound:

Which formula represents an isomer of this compound?

2.

3.

3.

4.

2.  Which two compounds have the same empirical formula?

1. C2H2 and C2H4

2. CH2 and C3H8

3. HO and H2O4. NO2 and N2O4

3.  Which compound is an isomer of C4H9OH?

1. C3H7CH3

2. C2H5OC2H5

3. C2H5COOC2H5

4. CH3COOH

4.  A characteristic of most organic compounds is that they

1. have low melting points2. have high melting points3. are soluble in water

4. conduct electricity when dissolved in water

5.  Which structural formula represents a molecule that is not an isomer of pentane?

1.3.

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2. 4.

6. All organic compounds must contain the element

1. phosphorus2. oxygen

3. carbon4. nitrogen

7. Base your answer to this question on the information below.

The formula below represents a hydrocarbon.

Which structural formula below shows an isomer of this hydrocarbon?

1.

2.

3.

4.

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8.  The three isomers of pentane have different

1. formula masses2. molecular formulas

3. empirical formulas4. structural formulas

9.  The isomers CH3OCH3 and CH3CH2OH differ in

1. molecular formula2. molecular structure

3. number of atoms4. formula mass

10.  Which two compounds have the same molecular formula but different chemical and physical properties?

1. CH3CH2Cl and CH3CH2Br2. CH3CHCH2 and CH3CH2CH3

3. CH3CHO and CH3COCH3

4. CH3CH2OH and CH3OCH3

11.  Which structural formula is incorrect?

1.

2.

3.

4.

12. Which statement explains why the element carbon forms so many compounds?

1. Carbon atoms combine readily with oxygen.2. Carbon atoms have a very high electronegativity.3. Carbon readily forms ionic bonds with other carbon atoms.4. Carbon readily forms covalent bonds with other carbon atoms.

13.  Compared to the rate of inorganic reactions, the rate of organic reactions generally is

1. slower because organic particles are ions2. slower because organic particles contain covalent bonds3. faster because organic particles are ions4. faster because organic particles contain covalent bonds

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14.  The compounds CH3OCH3 and CH3CH2OH are isomers of each other. These two compounds must have the same

1. density2. reactivity

3. melting point4. molecular formula

15.  In a molecule of CH4, the hydrogen atoms are spatially orientated toward the corners of a regular

1. pyramid2. tetrahedron

3. square4. rectangle

16.  The compounds C2H4 and C4H8 have the same

1. freezing point at standard pressure2. boiling point at standard pressure

3. molecular formula4. empirical formula

17. Which formula represents an unsaturated hydrocarbon?

1.

2.

3.

4.

18.  Which is an isomer of CH3CH2CH2COOH?

1. CH3CH2OCH2CH3

2. CH3CH2CH2OCH3

3. CH3CH2CH2CH2OH4. CH3COOCH2CH3

19.  Two substances have different physical and chemical properties. Both substances have molecules

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that contain two carbon atoms, one oxygen atom, and six hydrogen atoms. These two substances must be 1. isomers of each other

2. isotopes of each other3. the same compound4. the same hydrocarbon

20. What is the total number of valence electrons in a carbon atom in the ground state?

1. 62. 2

3. 124. 4

21. The isomers butane and methylpropane differ in their:

1. molecular formulas2. structural formulas

3. total number of atoms per molecule4. total number of bonds per molecule

22. Which compound is an isomer of pentane?

1. butane2. propane

3. methyl butane4. methyl propane

23. Which pair of compounds are isomers?

1. NO2 and N2O4

2. P2O5 and P4O10

3. HCOOH and CH3COOH4. CH3OCH3 and C2H5OH

What are the various Functional Groups?o Atoms or groups of atoms that replace hydrogen atoms in a hydrocarbon.o This will form new compounds?o They have distinct physical and chemical properties.o There are 9 functional groupso All found on Table R!

1. Halides A Halogen (F, Cl, Br, or I) replaces a hydrogen on a hydrocarbon.

o Used as organic solventso General Formula: R-X (X= Halogen & R= Alkyl group)o Add fluoro for F Designate the location of the halide with 1,2 etco Chloro for Clo Bromo for Bro Iodo for I

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2. Alcohols Organic compounds in which one or more hydrogen atoms are replaced by an –OH. -OH group is called a hydroxyl group. NOT A BASE! They are nonelectrolytes (Do not form ions in solution). Polar substances General Formula: R-OH Naming: Position of OH group must be assigned & -ANE ending changes to –OL. Classification of Alcohols

There are primary, secondary, and tertiary carbon atoms: Primary Carbon: Attached to one carbon only

Secondary: Attached to two carbon atoms

Tertiary: Attached to three carbon atoms.

3. Aldehydes Organic compounds in which a carbonyl group (C=O) is found on the end carbon (a

primary carbon): Naming: Substitute –AL in place of final –E of alkane name.

4. Ketones C=O group is on the inside of a hydrocarbon: Naming: Substitute –ONE in place of final –E of alkane name.

5. Ethers Two carbon chains are joined together by an oxygen atom: Naming: name the alkyl groups and add ether at the end. General Formula: R-O-R

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6. Organic Acids Organic compounds that have a Carboxyl group (-COOH): Naming: Substitute –OIC ACID in place of final –E in alkane name. Ethanoic acid= Acetic acid

7. Esters Have strong aromas; for example, flavorings in bananas, wintergreen, oranges. The fine smell of esters

8. Amines Formed when one or more of the hydrogen’s in ammonia is replaced by an alkyl group: Naming: Substitute –AMINE in place of final –E of alkane name.

9. Amides Formed by the combination of 2 amino acids: Form proteins Naming: Replace final –E with -AMIDE

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