Unit 14: ORGANIC CHEMISTRY

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Name: Date: Period: Unit 14: ORGANIC CHEMISTRY There are at least nine million organic compounds. What factors are responsible for the tremendous number of organic compounds?

Background: The term organic chemistry refers to the study of compounds containing carbon. The most common elements found with carbon are hydrogen, oxygen, nitrogen, phosphorus, and the halogens.

The name reflects the historical roots of chemistry it was thought that compounds obtained from living organisms required a vital force for their existence.

1 Name: Date: Period: Unit 14: ORGANIC CHEMISTRY There are at least nine million organic compounds. What factors are responsible for the tremendous number of organic compounds? What makes all of these compounds different? Building organic molecules using models can help us understand the basic structures of organic compounds. Background: The term organic chemistry refers to the study of compounds containing carbon. The most common elements found with carbon are hydrogen, oxygen, nitrogen, phosphorus, and the halogens. Organic compounds, then, can be defined as covalently bonded compounds containing carbon, excluding carbonates and oxides. The name reflects the historical roots of chemistry it was thought that compounds obtained from living organisms required a vital force for their existence. The notion was discarded in 1828, when the first organic compound was synthesized in the lab, but the name organic chemistry remains. Carbon is unique among the elements because of the large number of diverse structures of compounds that it forms. Several factors help explain why compounds containing carbon are well-suited to the chemistry of life: Carbon forms strong and stable bonds with other carbon atoms. Chains of carbon atoms can close in on themselves to form rings in addition to chains. Many different ring sizes are possible, but five-, six-, and sevenmembered rings are the most common. The valency of carbon is four carbon forms four covalent bonds to achieve a stable octet. Because of their small size, carbon atoms form strong multiple bonds (double and triple bonds) to other carbon atoms, as well as to nitrogen, oxygen, and sulfur atoms. Purpose: The purpose of this activity is to build organic molecules using models. The models will be used to draw structural formulas of organic compounds, determine the general formulas for different classes of hydrocarbons, and develop the concept of isomers of organic compounds.

2 Name: Date: Period: Introducing Organic Chemistry An Inquiry-Based Lesson 1. Review: Complete the table below using your molecular modeling kit and Periodic Table. Element Number of Lewis Dot Structure Number of valence e - Bonding Sites Color of atom in modeling kit Hydrogen Oxygen Nitrogen Carbon The HONC-1234 Rule Every Hydrogen has 1 bond connecting it to other atoms. Every Oxygen has 2 bonds connecting it to other atoms. Every Nitrogen has 3 bonds connecting it to other atoms. Every Carbon has 4 bonds connecting it to other atoms. 2. Define organic compound. 3. What is the common element in all organic compounds? 4. Identify five other elements frequently found bonded to carbon in organic compounds. 5. Give two examples of carbon-containing molecules that would not be considered organic. (a carbonate ) & (an oxide ) 6. Describe two factors that account for the multitude of organic compounds. 2 P a g e

3 7. Using your molecular model building kit, create four different organic compounds. Using the colored pencils, sketch your molecules below and determine their molecular formulas. CREATE A LABEL AND TAKE A PICTURE OF EACH MOLECULE YOU MAKE USING YOUR IPAD! 1) Create a 5-carbon hydrocarbon that is an alkane. A hydrocarbon is a molecule containing only carbon and hydrogen. An alkane has only single bonds. 2) Create an isomer of the molecule in Box #1. An isomer is a molecule that has the same molecular formula but different structural formula. Molecular Formula: Compound Name: Interesting Fact: Molecular Formula: Compound Name: methylbutane Interesting Fact: 3) Create a 6-carbon hydrocarbon that is an alkene. An alkene has at least one double bond. 4) Create a halocarbon that is an alkane. A halocarbon is a molecule containing only carbon, hydrogen, & a halogen. Molecular Formula: Compound Name: Interesting Fact: Molecular Formula: Compound Name: Interesting Fact: 5) Create a 3-carbon hydrocarbon that is an alkyne. A hydrocarbon is a molecule containing only carbon and hydrogen. An alkyne has at least one triple bond. 6) Create a cycloalkane. A cycloalkane is a ring-shaped hydrocarbon that only contains single bonds. Molecular Formula: Molecular Formula: Compound Name: propyne Compound Name: Interesting Fact: Interesting Fact: 3 P a g e

Questions for Discussion Be prepared to answer the following questions in the Nearpod activity at the end of the lesson. 1. ALKANES a. What is an alkane? b. How many ca

rmula for all alkanes? f. Without counting the atoms, determine the number of hydrogen atoms that would be present in hexane. 2. ISOMERS a. What is the same about the molecules in Box #1 and Box #2?

4 Questions for Discussion Be prepared to answer the following questions in the Nearpod activity at the end of the lesson. 1. ALKANES a. What is an alkane? b. How many carbons are in pentane? c. Which Reference Table lists the organic prefixes? d. What does the suffix -ane in pentane imply? e. Based on Reference Table Q, what is the general formula for all alkanes? f. Without counting the atoms, determine the number of hydrogen atoms that would be present in hexane. 2. ISOMERS a. What is the same about the molecules in Box #1 and Box #2? b. What is the difference between Box #1 & Box #2? 3. ALKENES a. How is an alkene different than an alkane? b. What does the number before the name represent? 4. HALOCARBONS a. What does the prefix halo mean? 5. ALKYNES a. How is an alkyne different than an alkene? b. What does the number before the name represent? 6. CYCLOALKANES a. What does the prefix cyclo mean? 4 P a g e

5 Name: Date: Pd. Aim: What are the properties of organic compounds? ORGANIC CHEMISTRY: Exceptions: Properties of Organic Compounds 1. Carbon has valence electrons & can therefore form covalent bonds. Draw each structure and add hydrogen atoms as needed in the table below. (1) (3) (2) (4) 2. Carbon s bonds may be,, or. a. Orbital Notation: b. Valence dot diagram: 5 P a g e

6 3. Most organic compounds are or weakly polar. a. IMF present in nonpolar molecules: b. Low and points. c. High vapor pressure ( ). d. /immiscible in water, but soluble in solvents, such as carbon tetrachloride & benzene. 4. except for organic acids in the aqueous state. 5. Organic reactions, being complex, are much than inorganic reactions. a. Since organic compounds are formed by bonding nonmetals, it takes a lot more energy to break a covalent bond than an ionic bond. b. Activation energies are. 6. Carbon compounds are extremely. a. Carbon can bond with other carbons to form,, and. b. There are millions of organic compounds known, and that number grows daily. 6 P a g e

7 Applying Your Knowledge Practice Regents Questions 1. Organic compounds differ from inorganic compounds in that organic compounds generally have (1) high melting points and are electrolytes (2) high melting points and are nonelectrolytes (3) low melting points and are electrolytes (4) low melting points and are nonelectrolytes 2. Which element is composed of atoms that can form more than one covalent bond with each other? (1) hydrogen (2) helium (3) carbon (4) calcium 4. Draw an electron dot diagram of methane in the space below. 5. Is water an appropriate solvent for methane? Why or why not? 6. Hydrocarbons are compounds that contain (1) carbon, only (2) carbon and hydrogen, only (3) carbon, hydrogen, and oxygen, only (4) carbon, hydrogen, oxygen, and nitrogen, only 7. Which structural formula correctly represents a hydrocarbon molecule? (1) (2) (3) (4) 8. Which atoms can bond with each other to form chains, rings, or networks? (1) carbon (2) hydrogen (3) oxygen (4) nitrogen 9. Organic compounds that are essentially non-polar and exhibit weak intermolecular forces have (1) low vapor pressure (3) low melting points (2) high melting points (4) high electrical conductivity in solution 10. In general, which property do organic compounds share? (1) high melting point (3) high electrical conductivity (2) readily soluble in water (4) slow reaction rate 7 P a g e

8 Aim: How can organic compounds be classified? Hydrocarbons Aromatic Aliphatic Aromatic Hydrocarbons Compound Name Molecular Formula Structural Formula Line Representation 8 P a g e

9 Homologous Series: See Reference Table Aliphatic Hydrocarbons Alkanes Alkenes Alkynes Saturated Hydrocarbon: Unsaturated Hydrocarbon:

10 Alkanes (Single Bonds Only): # of Carbons IUPAC Name Based on Reference Table O Molecular Formula Summarizes the amount of each type of atom; does not show arrangement of atoms Structural Formula Shows arrangement of atoms in two-dimensional space. Condensed Structural Formula Shows arrangement of atoms, takes up less space than structural formula. 1 CH 4 CH 4 ethane CH 3 CH 2 CH 3 C 3 H 8 butane P a g e

11 Alkenes (At least one double bond): # of Carbons 1 IUPAC Name Based on Reference Table O Methene doesn t exist! Why? Molecular Formula Summarizes the amount of each type of atom; does not show arrangement of atoms Structural Formula Shows arrangement of atoms in two-dimensional space. Condensed Structural Formula Shows arrangement of atoms, takes up less space than structural formula. ethene CH 2 CH 2 propene C 3 H 6 2-butene 5 1-pentene 3-hexene 3-heptene Why can t methene exist? Why can t 4-heptene exist? 11 P a g e

12 Alkynes (At least one triple bond): # of Carbons 1 IUPAC Name Based on Reference Table O Methyne doesn t exist! Why? Molecular Formula Summarizes the amount of each type of atom; does not show arrangement of atoms Structural Formula Shows arrangement of atoms in two-dimensional space. Condensed Structural Formula Shows arrangement of atoms, takes up less space than structural formula. ethyne CH CH propyne C 3 H 4 2-butyne 5 1-pentyne 3-hexyne Summing It Up: Define saturated or unsaturated using your glossary in the boxes below. Saturated Hydrocarbon Unsaturated Hydrocarbon 12 P a g e

Aim: How are branched hydrocarbons named? 1. The number of carbons in the longest continuous unbroken chain is used to determine the prefix of the parent chain. 2.

13 Aim: How are branched hydrocarbons named? 1. The number of carbons in the longest continuous unbroken chain is used to determine the prefix of the parent chain. 2. The position of any alkyl group is considered next. To name the alkyl group, use the prefix for the number of carbons in the alkyl group, replace the -ane suffix with -yl. 3. Use a number to identify which carbon the alkyl group is attached to. Remember to number the carbons so that the alkyl group is on the LOWEST number ( shortest address ). Example: 4. When there is more than one of the same type of alkyl group branching off of the main carbon chain, use the Greek prefixes to indicate how many, i.e., di- (2); tri- (3); tetra- (4); and so on. The position of the alkyl groups is also specified using numbers. Example: 5. When different alkyl groups are present on the chain, they are given in alphabetical order. Example: 6. In unsaturated compounds, the double or triple bond MUST be included in the main chain. Even with alkyl groups present, the double/triple bond is assigned the lowest possible number. Alkyl groups are named first, and double/triple bonds are named after. Example:

14 Practice Naming These Hydrocarbons Name the compounds below according to the IUPAC naming system. Be sure to HIGHLIGHT the parent chain and NUMBER THE CARBONS first! Find the longest possible chain, giving the substituents (i.e., alkyl groups) the lowest possible address. CH 3 CH 3 CH CH 2 CH IUPAC Name: CH 3 CH 3 CH 3 CH CH CH IUPAC Name: CH 3 CH 3 CH 2 C CH 3 CH 3 CH CH 3 CH CH 2 CH CH 2 CH 2 CH CH 2 CH 3 CH 2 CH 3 **Remember to find the longest parent chain!** IUPAC Name: IUPAC Name: CH 3 CH 2 CH C CH 2 CH CH2 CH CH 3 CH 3 CH C C CH 3 CH 3 CH 3 CH 3 IUPAC Name: IUPAC Name: CH 3 C C CH 2 CH 3 IUPAC Name: CH 3 CH 2 C C CH 2 CH 3 CH 3 CH 2 CH3 IUPAC Name: 14 P a g e

15 Practice Drawing These Hydrocarbons Draw the structural representation of each compound below. Remember: Each carbon bonds four times! ethane 1-butyne 1,4-pentadiene (Hint: This means that there are two double bonds!) 3-methyl-1-butyne 3,3-dimethyl pentane 2-ethyl-1-pentene 2,2,4,4-tetramethylpentane 2-ethyl-3-methyl-1-butene 15 P a g e

16 Aim: What is an Isomer? How can two different compounds have the same molecular formula, but different structures & different physical structures & chemical properties? Isomer: Butane Molecular Formula: Structural Diagram: Methylpropane ( ) Molecular Formula: Structural Diagram: Draw all possible isomers for pentane. IUPAC name: IUPAC name: IUPAC name: Structural Diagram: Structural Diagram: Structural Diagram: Molecular Formula: Molecular Formula: Molecular Formula: 16 P a g e

17 Draw the 5 isomers for hexane (including hexane) and name them. 17 P a g e

$Aim: How are the processes of fractional distillation and cracking used to convert hydrocarbons into useful forms?$ Then use the diagram below and your knowledge of hydrocarbons to complete the table. FRACTIONAL DISTILLATION 1. What is crude oil? (Add to this definition at 1:11.) 2. Where is crude oil harvested? 3.

Then use the diagram below and your knowledge of hydrocarbons to complete the table. FRACTIONAL DISTILLATION 1. What is crude oil? (Add to this definition at 1:11.) 2. Where is crude oil harvested? 3.

18 Aim: How are the processes of fractional distillation and cracking used to convert hydrocarbons into useful forms? Instructions: Watch the YouTube videos about fractional distillation and cracking using your ipad (or phone) to answer the questions. Then use the diagram below and your knowledge of hydrocarbons to complete the table. FRACTIONAL DISTILLATION 1. What is crude oil? (Add to this definition at 1:11.) 2. Where is crude oil harvested? 3. What does crude oil provide us with? 4. As the length of molecules increases, what happens to IMF? 5. Compare the boiling point of short hydrocarbons to the boiling point of long hydrocarbons. 6. Summarize the process of fractional distillation. 7. What is a fraction? 8. Using the diagram at right, what is the boiling point of pentane? 9. What can pentane be used for? 10. Identify another hydrocarbon that is part of the same fraction as pentane. Molecular formula: IUPAC Name: 18 P a g e

HYDROCARBON CRACKING 1. What is crude oil a mixture of? 2. Shorter Hydrocarbon Chains Longer Hydrocarbon Chains 3. Why is there a demand for short-chain hydrocarbons? 4.

19 HYDROCARBON CRACKING 1. What is crude oil a mixture of? 2. Shorter Hydrocarbon Chains Longer Hydrocarbon Chains 3. Why is there a demand for short-chain hydrocarbons? 4. What does the process of cracking do? 5. Why is this beneficial? 6. What are the longer hydrocarbon chains broken down into? & 7. The alkanes are used for fuels. What can the alkenes be used for? 8. Write two possible equations for the cracking of octane: Chemical Formula: Word Formula: Chemical Formula: Word Formula: 9. What are the two types of cracking? & Practice Regents Questions: 1. During fractional distillation, hydrocarbons are separated according to their a) boiling points b) melting points c) triple points d) saturation points 2. In terms of intermolecular forces, explain the relationship between hydrocarbon chain length and boiling point. 19 P a g e

20 Name: Date: Period: Aim: What functional groups exist among organic compounds? Functional Group: Reference Table Functional groups are collections of atoms in organic chemistry molecules that contribute to the chemical characteristics of the molecule and participate in predictable reactions. These groups of atoms contain oxygen or nitrogen or sometimes sulfur attached to a hydrocarbon skeleton. Organic chemists can tell a lot about a molecule by the functional groups that make up a molecule. I. Halides (a.k.a. halocarbons) R represents Halocarbon Nomenclature Structural Diagram 1,2-difluoroethane 1,4-dichloropentane Identify two isomers from the chart above: & 20 P a g e

21 II. Organic Acids Organic acids contain a -COOH functional group, also called a carboxylic acid functional group. The -COOH group is always terminal (at the end of the chain, not in the middle). To name organic acids, replace the suffix of the parent chain (i.e., -ane, -ene, or -yne ) with the suffix -oic acid. ) Organic Acid Nomenclature Structural Diagram III. Ketones Ketones contain an internal (non-terminal) carbonyl group (highlight it above). To name ketones, replace the suffix of the parent chain (i.e., -ane, -ene, or -yne ) with the suffix -none. ) Ketone Nomenclature Structural Diagram 2-hexanone 21 P a g e

22 IV. Aldehydes Aldehydes contain a terminal carbonyl group (highlight it above.) To name aldehydes, replace the suffix of the parent chain (i.e., -ane, -ene, or -yne ) with the suffix -al. ) Aldehyde Nomenclature Structural Diagram hexanal Practice Regents Questions 1. Methanal is the IUPAC name for an a) acid b) alcohol c) ketone d) aldehyde 2. Which organic compound is an acid? (Hint: Use Table Q/Draw structural diagrams to help you.) a) CH 3 OH b) CH 3 OCH 3 c) CH 3 COOCH 3 d) CH 3 COOH 3. Which structural formula represents a ketone? 4. What is the correct IUPAC name for the following structure: a) 2,4-dichlorobutane b) 2,4-dichloropentane c) 1,3-dichloropentane d) 1,3-dichlorobutane 22 P a g e

V. Ethers Ethers contain two alkyl radicals (R groups) connected by an oxygen bridge. The two alkyls can be the same or different. If they are the same, use the prefix -di.

23 V. Ethers Ethers contain two alkyl radicals (R groups) connected by an oxygen bridge. The two alkyls can be the same or different. If they are the same, use the prefix -di. To name ethers, name each alkyl group and add the word ether. Name the shorter alkyl group first. Ether Nomenclature Structural Diagram diethyl ether VI. Esters Esters contain one oxygen in the middle of a carbon chain, and a second oxygen as part of a carbonyl group. (Think ester has plural (2) oxygens!) To name esters, name the alkyl group that is singly-bonded to the oxygen. Then name the alkyl group which contains a carbon that has a double-bonded oxygen, changing the suffix to -oate. Ester Nomenclature Structural Diagram pentyl ethanoate 23 P a g e

24 VII. Amines Amines contain an -NH 2 group. To name amines, identify the alkane from which the amine was derived and replace the suffix with -amine. Use a number in front of the name to indicate position of amine group if the molecule has three or more carbons. Amine Nomenclature Structural Diagram 2-pentanamine VIII. Amides Amides contain a terminal -CONH 2 group. To name amides identify the alkane from which the amide was derived and replace the suffix with -amide. Amide Nomenclature Structural Diagram 24 P a g e

25 IX. Alcohols Alcohols are hydrocarbons that contain a hydroxyl (-OH) group somewhere on the chain. To name alcohols, identify the alkane from which the alcohol was derived and replace the suffix with -ol. If there is more than one possible isomer, identify the location of the OH group with a number. Alcohol Nomenclature Structural Diagram 1,2-pentandiol (Note: -diol indicates that there are 2 hydroxyl groups present.) ( -triol would indicate that there are hydroxyl groups present.) 25 P a g e

26 Aim: What is the difference between a monohydroxy alcohol and a primary alcohol? and a dihydroxy alcohol vs. a secondary alcohol? and a trihydroxy alcohol vs. a tertiary alcohol? Alcohols MONOHYDROXY, DIHYDROXY, & TRIHYDROXY ALCOHOLS Classifying Alcohols Based on Number of Hydroxyl Groups Monohydroxy Alcohols (Contain hydroxyl (-OH) group.) methanol ethanol 2-propanol Structural Formula: Structural Formula: Structural Formula: Dihydroxy Alcohols (Contain hydroxyl (-OH) groups.) 1,2-ethandiol Structural Formula: 1,4-butandiol Structural Formula: Trihydroxy Alcohols (Contain hydroxyl (-OH) groups.) 1,2,3-propantriol (a.k.a. glycerol/glycerin) Structural Formula: 1,3,5-hexantriol Structural Formula: 26 P a g e

PRIMARY, SECONDARY, & TERTIARY ALCOHOLS Classifying alcohols based on the number of R-groups that are attached to the carbon attached to the hydroxyl group (-OH) Type of Alcohol Primary Alcohol

27 PRIMARY, SECONDARY, & TERTIARY ALCOHOLS Classifying alcohols based on the number of R-groups that are attached to the carbon attached to the hydroxyl group (-OH) Type of Alcohol Primary Alcohol Secondary Alcohol Tertiary Alcohol General Formula # of carbons attached to the C-OH Example (Structural Formula & IUPAC Name) Summary: Alcohols can be classified based on: 1., i.e., monohydroxy alcohol, dihydroxy alcohol, trihydroxy alcohol 2.,, i.e., primary alcohol, secondary alcohol, tertiary alcohol Practice Regents Questions 1. When the name of an alcohol is derived from the corresponding alkane, the final -e of the name of the alkane should be replaced with a) -al b) -ole c) -one d) -ol 2. To be classified as a tertiary alcohol, the functional OH group is bonded to a carbon atom that must be bonded to how many additional carbon atoms? a) 1 b) 2 c) 3 d) 4 3. Which is the structural formula of a dihydroxy alcohol? 27 P a g e

28 4. Which is the structural formula of a primary alcohol? 5. Which is the structural formula of a secondary alcohol? 6. All three of the following alcohols can be classified as a) secondary alcohols b) monohydroxy alcohols c) tertiary alcohols d) primary alcohols 11. Which compound is a dihydroxy alcohol? a. C 3 H 5 (OH) 3 b. C 2 H 4 (OH) 2 c. Al(OH) 3 d. Ca(OH) What is the total number of OH groups in a molecule of glycerol? a. 1 b. 2 c. 3 d P a g e

29 Aim: What other functional groups exist among organic compounds? Do Now: The following examples illustrate the great variety of functional groups present in organic compounds. Circle and label the organic functional groups in the following compounds. An example has been done for you. 1. Functional Group: Ether IUPAC Name: Dimethyl ether 2. Functional Group: IUPAC Name: 3. Functional Group: IUPAC Name: 4. Functional Group: IUPAC Name: 5. Functional Group: IUPAC Name: 6. Functional Group: IUPAC Name: 7. Functional Group: IUPAC Name: 8. Functional Group: IUPAC Name: 29 P a g e

30 Aim: What types of reactions do hydrocarbons undergo? I. COMBUSTION General Formula: + + Example: Write the balanced equation for the combustion of octane (Use Table I!): II. SUBSTITUTION General Formula: + + If a saturated hydrocarbon (alkane) is reacted with a halogen, one of the halogen atoms replaces a hydrogen on the hydrocarbon chain. The hydrogens get replaced ONE AT A TIME. The reactive halogen atoms substitute for hydrogen atoms, hence the name. Substitution Example #1: Word Equation: Ethane + Fluorine + Structural Diagram Representation: Substitution Example #2: Word Equation: Butane + Bromine + Structural Diagram Representation: 30 P a g e

31 II. ADDITION General Formula: + + If an unsaturated hydrocarbon (alkene or alkyne) is reacted with a halogen, the mechanism of the reaction is such that the multiple bond is broken, and the halogen adds on at the site of the newly available bonds. Addition Example #1: Word Equation: Ethene + Fluorine Structural Diagram Representation: The fluorine atoms are added to the site of the double broken bond, one fluorine on one carbon and one fluorine on the other carbon. Addition Example #2: Word Equation: 1-Butyne + Bromine Structural Diagram Representation: Think about it: Which reaction, addition or substitution, would produce 1,4-dichlorobutane? Which reaction, addition or substitution would produce 2,3-dichlorobutane? 31 P a g e

32 Compare & Contrast Addition & Substitution Reactions 1. Write the reaction that occurs between propane and bromine a) as a structural representation: b) in words: Write the reaction that occurs between 1-butene and bromine a) as a structural representation: b) in words: + Practice Regents Questions 1. What type of reaction is represented by the equation below? a) substitution b) esterification c) fermentation d) addition 2. In which type of reaction can an unsaturated hydrocarbon become saturated? a) substitution b) esterification c) fermentation d) addition 3. The products of the complete combustion of a hydrocarbon are water and a) carbon dioxide b) an aldehyde c) an alcohol d) carbon 4. Which compound will undergo a substitution with bromine? a) C 3 H 6 b) CH 4 c) C 4 H 8 d) C 2 H 4 5. In the reaction, what is the structural formula of the product represented by X? 32 P a g e

33 II. ESTERIFICATION General Formula: + + Esterification is a dehydration synthesis reaction between an organic acid and an alcohol, where a water molecule is removed and an ester is formed. Esters typically have pleasant-smelling aromas, such as wintergreen, banana, pineapple, and pear. Esterification Example #1: Word Equation: Propanoic acid + methanol + water Structural Diagram Representation: Esterification Example #2: Word Equation: ethanoic acid + 1-butanol + water Structural Diagram Representation: Practice Regents Questions 1. An alcohol and an organic acid are combined to form water and a compound with a pleasant odor. This reaction is an example of a) saponification b) esterification c) polymerization d) fermentation 2. Which equation represents an esterification reaction? a) C 5 H 10 + H 2 C 5 H 12 b) C 6 H 12 O 6 2C 2 H 5 OH + 2CO 2 c) C 3 H 8 + Cl 2 C 3 H 7 Cl + HCl d) HCOOH + CH 3 OH HCOOCH 3 + HOH 33 P a g e

V. Polymerization: A) Addition Polymerization: Monomers react by addition to form polymers. In order to undergo addition, the reactants must be unsaturated (contain double or triple bonds).

B) Condensation Polymerization: Monomers that have functional groups that contain O and H react to form polymers by dehydration synthesis the removal of water).

34 V. Polymerization: A) Addition Polymerization: Monomers react by addition to form polymers. In order to undergo addition, the reactants must be unsaturated (contain double or triple bonds). These polymers can be thousands of units long, which can be denoted by a subscript n as shown below. B) Condensation Polymerization: Monomers that have functional groups that contain O and H react to form polymers by dehydration synthesis the removal of water). Synthetic polymers, such as PVC, Teflon, and polyester, are man-made. There are many natural polymers in existence as well, including cellulose, starch, and proteins. Practice Regents Questions 1. The chaining together of small molecules (monomers) to form a large molecule (polymer) occurs during the process of a) substitution b) fermentation c) saponification d) polymerization 2. The reaction nc 2 H 4 (C 2 H 4 )n is best described as a) substitution b) fermentation c) saponification d) polymerization 3. The process of opening double bonds and joining monomer molecules to form polyvinyl chloride is called a) addition polymerization b) dehydration polymerization c) condensation polymerization 34 P a g e

35 VI. FERMENTATION General Formula: + + Fermentation is the decomposition of glucose or fructose into an ethanol and carbon dioxide. Yeast and enzymes such as zymase facilitate this process. Example: Fermentation of Glucose Word Equation: + Chemical Equation: + VII. SAPONIFICATION General Formula: + + Saponification is the splitting of a fat by a strong base (i.e., NaOH) to produce glycerol and soap molecules. Example of Saponification 35 P a g e

36 Practice: Types of Reactions 1. Identify the type of rxn by writing it in the specified box. Each type of reaction occurs only once. Reaction Type of Reaction How Do You Know? C2H4 + Cl2 C2H4Cl2 CH3OH + CH3COOH CH3COOCH3 + H2O CH4 + 2 O2 CO2 + 2 H2O C6H12O6 2 C2H5OH + 2 CO2 C3H8 + HBr C3H7Br + H2 CH3OH + CH3OH CH3OCH3 + H2O etherification 1200 C2H4 -(-C2H4-) Identify the type of reaction taking place and name each of the reactants and products. Reaction Type: Reaction Type: 3) The reaction that occurs when a hydrocarbon is heated in the presence of oxygen is called a) combustion b) fermentation c) saponification d) vulcanization 4) The cross-linking of rubber molecules with sulfur to toughen it is called a) combustion b) fermentation c) saponification d) vulcanization 5) The reaction that is used to manufacture soap is called a) combustion b) fermentation c) saponification d) vulcanization 6) The reaction that produces ethanol by the digestion of sugars by yeast is called a) combustion b) fermentation c) saponification d) vulcanization 7) Which reaction can be used to make 2,3-dichloropentane? a) addition b) substitution c) etherification d) esterification 8) Which reaction can be used to make propyl ethanoate? a) addition b) substitution c) etherification d) esterification 9) What is a by-product of saponification? a) ethanoic acid b) propanone d) ethylene glycol d) glycerol 36 P a g e

37 Name: Date: Period: I. Introduction to Organic Chemistry Organic Chemistry Review Sheet 1. Which of the following compounds is formed by covalent bonding? a) Na2S b) AlCl3 c) C6H12O6 d) LiH 2. Which of the following molecules contains a nonpolar covalent bond? a) H2O b) HF c) F2 d) NH3 3. Which of the following molecules is polar? (Circle all that apply.) a) H2O b) HF c) F2 d) NH3 4. Which of the following molecules has the strongest London dispersion force attractions? a) CH 4 b) C 2 H6 c) C 3 H8 d) C 4 H Which of the following nonpolar molecules has the lowest boiling point? a) CH 4 b) C 2 H 6 c) C 3 H 8 d) C 4 H Which of the following substances is organic? a) NaCl b) NH 3 c) CH 4 d) H 2 O 7. Which of the following substances is insoluble in water? a) NaCl b) NH 3 c) CH 4 d) H 2 O 8. When 2 carbon atoms form a double bond, how many pairs of e- will be shared between them? 9. An organic compound is heated in the presence of oxygen. If a high enough temperature is reached, what chemical reaction will take place? 10. An alkane has 5 carbon atoms. How many hydrogen atoms will it have? 11. An alkene has 3 carbon atoms. How many hydrogen atoms will it have? 12. An alkyne has 4 carbon atoms. How many hydrogen atoms will it have? 37 P a g e

38 II. Naming & Drawing Simple Organic Molecules A) Name the following compounds: 7. C 2 H 6 ; Homologous Series: 8. C 3 H 4 ; Homologous Series: 9. C 4 H 8 ; Homologous Series: B) Draw the following compounds. Then, draw and name one isomer of the compound. Butane Isomer of Butane ( ) Butyne Isomer of Butyne ( ) Pentane Isomer of Pentane ( ) 38 P a g e

39 III. Naming & Drawing Substituted Hydrocarbons A) Name the following compounds: B) Draw the following compounds. 2 chloro propane 1,2 dichloro butane 1,4 dichloro pentane 3 methyl heptane 2,2 dimethyl octane 3,4-dichloro-1,3-hexadiene 39 P a g e

40 IV. Organic Chemical Reactions 1. Which of the following reactions is an addition reaction? a) C2H6 + Cl2 --> C2H5Cl + HCl b) C2H6 + Cl2 --> C2H5Cl + HCl c) C2H4 + Cl2 --> C2H4Cl2 d) C3H8 + HBr --> C3H7Br + H2 2. Which of the following hydrocarbons can undergo an addition reaction? a) C 3 H 8 b) C 4 H8 c) C 5 H 12 d) CH 4 3. Which of the following products can form when propane reacts with diatomic chlorine? a) C 3 H 8 Cl2 b) C 3 H 7 Cl2 c) C 3 H 6 Cl 2 d) C 3 H 8 Cl 4. Complete the following reactions and indicate whether they are addition or substitution reactions. Give the name of the organic reactants and products, only. a) b) c) d) 5. State what kind of reaction can form the following products and identify the reactants that are needed to make those products. a) 1 fluoro butane Type of reaction: Reactants needed: b) 1,2 dichloro butane Type of reaction: Reactants needed: 40 P a g e

41 V. Functional Groups A) Draw the structures of the following organic compounds and indicate if the functional group is attached to a primary or secondary carbon. 2-pentanone Name Functional Group Structural Formula Propanoic acid Ethanamine Butanamide Methyl ethanoate Methyl propyl ether 2- pentanol BE SPECIFIC! 1-pentanol BE SPECIFIC! B) Which of the following molecules is an isomer of propanol? a) propanone b) methyl ethyl ether c) propanal d) propanoic acid ***NOTE*** Don t forget to review the organic reactions Let s Practice handout on page 33, as well as the videos on fractional distillation and cracking on Ms. Roman s website. 41 P a g e

Aim: Sorting Out Organic Compounds!

Aim: Sorting Out Organic Compounds! Name: Organic Chemistry Organic chemistry is a highly creative science in which chemists create new molecules and explore the properties of existing compounds. There are at least nine million organic compounds.