Packet 11 Unit 7 Chapters 22 & 23 Lessons 62 67

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1 Lesson Topic Chapter Sections Assignment Material & 22.3 WorksheetLesson64 (Includesbookquestions) Worksheets29-4through29-7 (Classify& name) Q 13, 14, 15, 26, 28, 29, 30, 31, 48, 49 and 72 Worksheets30-3through & 23.3 Q 1, 2, 7, 10, and 49 Classes of Organic Compounds, Properties & Isomers UnsaturatedHydrocarbons & Hydrocarbon rings OtherOrganicCompounds: Alcohols, ethers, esters, aldehydes, ketones, amines, acids Packet 11 Unit 7 Chapters 22 & 23 Lessons worksheet-organicreactions & 23.4 Q 36 a, b, 17, 46 and RPE 23 (1-15) Review Pages and & 619 OrganicReactions ReviewofOrganicCompounds Test Organic Compounds Topic Test

2 \\POLAND_LAB\SYS\Teachers\BaSmith\Chemistry\O Chem\Introduction to Organic Chemistry.doc Major Understandings ff, gg, ii and 5.2 e Unit 7 Lesson Introduction to Organic Chemistry Lesson 62 Pre-Assignment None I. Organic Compounds any compound that contains the element Carbon. Actually oxides and carbonates aren t considered organic. A. Factors that account for Properties. 1. Bonding is usually covalent since Carbon s electronegativity is 2.5 and the difference needs to be 1.7 or more to be ionic. 2. Carbon is in group 14 so it has 4 valence electrons once it undergoes sp 3 hybridization. Carbon is unique because of its ability to combine with itself as well as other elements.. 3. Molecules are usually nonpolar, due to symmetry B. Properties 1. Usually have low melting points. (mp <400) Occur as gases, liquids, or soft solids. (Held together by van der Waal forces) 2. Strong odor. (High vapor pressure) Gasoline, Acetone. 3. Do not conduct electricity. (Nonpolar) Inorganic (acids, bases, or salts) 4. Insoluble in polar solvents. (Likes dissolve likes) 5. Most will burn in air. Propane, octane, alcohol. 6. Most react slowly. Covalent react slower than ionic. C. Isomers compounds that have the same molecular formula (molecular mass, but different structural formulas. 1. Structural formulas show how the different atoms are arranged. Very important in O. Chemistry since the same atoms often arrange in more than one way. 2. Examples a. CH 4 (No) b. C 2 H 6 (No) c. C 3 H 8 (No) d. C 4 H 10 (YES!) e. C 2 H 5 Cl (No) f. C 2 H 4 Cl 2 (YES!) D. Saturated & Unsaturated Compounds 1. Saturated - compounds that have all four bonds on each carbon filled. (All single bonds) 2. Unsaturated at least one double or triple bond exists between two neighboring carbons. Ex. C 2 H 4 (yes), CH 3 COCH 3 (no) E. Hydrocarbons compounds that contain only hydrogen and carbon. (Petroleum and natural gas.)

3 \\POLAND_LAB\SYS\Teachers\BaSmith\Chemistry\O Chem\Introduction to Organic Chemistry.doc Hydrocarbons open-chain (aliphatic) Cyclic straight branched 1. Classifying chain a. Alkanes aliphatic (open chained) and contain only single bonds b. Alkenes aliphatic and contains one double bond. c. Alkynes aliphatic and contains one triple bond. d. Alkadienes aliphatic and contains two double bonds. e. Alicyclic arranged in a circle. f. Aromatics 6 carbons arranged in a circle with alternating single and double bonds. 2. Chains may have any length from one to thousands a. Shortest are gases b. medium are liquids c. Longest are solids. Why? (van der Waal forces) d. Prefixes (Table P) 1. Meth 6. Hex 2. Eth 7. Hept 3. Prop 8. Oct 4. But 9. Non 5. Pent 10. Dec Assignment 62 Chapter 22 Q 2, 3, 4, 5, 6, 7, 8, 9, 22, 35, 49 and 54

4 Lesson 63 Organic Chemistry Day 2 I. Hydrocarbons (Table ) A. Alkanes contain only bonds. 1. They are known as the. The large ones are. 2. They are relatively. Why? (They are ) 3. 1 st are (up to ), the next are liquids, and the larger ones are. Why? 4. Naming uses the system of nomenclature. (International Union of Pure and Applied Chemists) a. all the carbons are in a 1. Count the number of and use the appropriate. 2. Add the suffix Practice 1: Practice 2: Draw ethane b. Branched a branching off of a chain of. 1. The compound bears the name of the. C C C C C C What is its last name? C 2. Number the carbons of the chain so that the or group comes off the number possible. Practice on the above example. Determine the names of the attached to the carbon chain. You don t have to worry about (Some on Table ) a. Methyl b. Ethyl c. Chloro d. Br e. Fluoro f. Nitro If a particular appears more than once use the prefix for 2 and for 3. Cl

5 Practice 1: Cl - C C C C C Cl F F Practice 2: Draw 1, 3, 4 tribromo 2,4 dinitro hexane B. Alkenes have a bond between neighboring carbons. 1. General Formula Why 2 less H? 2. Greater since they are 3. No. 4. Naming - Same as for except 1. ending is 2. must tell where the is. Example A: Example B: Draw an isomer of A C. Alkynes have a bond between two neighboring carbons. 1. General Formula Formula for butyne 2. Naming a. ending is Draw 2 hexyne D. Alkadienes have double bonds 1. Name ends with Example

6 E. Cyclic are arranged in a 1. Prefix - Try 1, 3 dichloro 4cyclopentene F. Aromatics series 1. General Formula 2. Resonance the alternating of and bonds in a ring. 3. Members a. First Formula isomers b. Second Formula isomers c. Third Formula isomers Assignment #63 Worksheets 29 4 through 29 7 (classify and name) Chapter 22 Q 13, 14, 15, 26, 28, 29, 30, 31, 48, 49, and 72

7 Assignment for Lesson Classify the hydrocarbons on pages 29-4 and 29-5 in the packet. 2. Draw the 5 isomers of C 6 H General Formulas a. What is the formula for hexane? b. Is C 5 H 8 an alkane? c. What is the formula for the alkane with 10 carbons? d. Write the formulas for the next three alkanes after methane (CH 4 ). Ethane Propane Butane. What does each member differ by? 4. Properties of Organic Compounds. a. Boiling points (high or low) b. Conductivity (poor or good) c. Combustibility in air (poor or good) d. Odor (strong or weak) e. React (quickly or slowly) f. Solubility in water (soluble or insoluble) g. Bonding (covalent or ionic) 5. Textbook questions from chapter 22. Questions 7, 8, and Circle the saturated compound(s).

8 F:\Teachers\BaSmith\Chemistry\O Chem\Naming Hydrocarbons.doc Major Understandings ff, gg, and 5.2 e Unit 7 Lesson Naming Hydrocarbons Lesson 63 Pre-Assignment Chapter 22 Q 2, 3, 4, 5, 6, 7, 8, 9, 22, 35, 49 and 54 I. Hydrocarbons (Table Q) A. Alkanes 1. General formula C n H 2n+2 where n is the number of Carbons Ex. Is C 6 H 16 an alkane? No Ex. What is the formula for the alkane with 4 Carbons? C 4 H They are known as the paraffins. The large ones are waxes. 3. They are relatively unreactive. Why? (They are saturated) 4. First four are gases, next 12 are liquids, and larger are solids. 5. Naming uses the IUPAC system of nomenclature. (International Union of Pure and Applied Chemists) a. Un-branched all the carbons are in line 1. Count the number of carbons and use the appropriate prefix. 2. Add the suffix ane b. Branched a carbon branching of a chain of carbons. 1. The compound bears the name of the longest carbon chain. C C C C C C C Pentane or Hexane 2. Number the carbons of the longest chain so that the branch comes off the smallest number possible. (Bottom up in the above example) 3. Determine the names of the groups attached to the carbon chain. (Some on Table R) a. Methyl CH 3 b. Ethyl C 2 H 5 c. Chloro Cl d. Bromo Br e. Fluoro F f. Nitro NO 2 4. If a particular group appears more than once use the prefix di for 2 and tri for 3. Cl Cl - C C C C C Cl F F 1,1,5 trichloro 3,4 difluoropentane B. Alkenes have a double bond between two neighboring carbons. 1. General Formula C n H 2n (double bond- double the carbons) 2. Greater reactivity since they are unsaturated 3. No Methene. Why not? (double bond between 2 carbons) 4. Naming a. Same as for alkanes except 1. ending is ene

9 F:\Teachers\BaSmith\Chemistry\O Chem\Naming Hydrocarbons.doc C. D. E. F. 2. must tell where the double bond is. Ex. C C C C = C (1 pentene) C C = C C C (2 pentene an isomer of above) Alkynes have a triple bond between two neighboring carbons. 1. General Formula C n H 2n-2 (note pattern) Formula for butyne (C 4 H 6 ) 2. Naming a. ending is yne Ex. 2 hexyne Alkadienes have two double bonds 1. Name ends with diene Cyclic are arranged in a circle 1. Name starts with cyclo- Try 1,3 dichloro 4cyclopentene Aromatics Benzene series 1. General Formula C n H 2n-6 2. Resonance the alternating of single and double bonds in a benzene ring. 3. Symbol 4. Members a. First Benzene C 6 H 6 No isomers b. Next Toluene C 7 H 8 No isomers c. Third Xylene C 8 H 10 Three isomers 1. Ortho next 2. Meta middle 3. Para across Assignment 63 Worksheets 29 4 through 29 7 (classify and name) Chapter 22 Q 13, 14, 15, 26, 28, 29, 30, 31, 45, 46, and 69

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14 Classes of Organic Compounds I. Other Organic Compounds hydrocarbons are only one group of organic compounds. A. Functional groups the atom or group of atoms that characterize a family of organic compounds and determine its. B. Hydrocarbon Radical all the and not involved in the functional group. (Represented by R and R ) Ex. C C C C OH Circle the functional group. Box the hydrocarbon radical. What is wrong with the structural diagram? II. Classes A. Alcohol organic compound in which one or more atoms have been replaced with a ( ) 1. Produced during the process of 2. Naming change the ending to and tell where the OH is if its not on the. 3. Types a. Monhydroxy have only -OH group 1) Primary - with the is connected to other carbon. Ex. 2) Secondary - with the is connected to other carbon. Ex. 3) Tertiart - with the is connected to other carbon. Ex. b. Dihydroxy have -OH groups ( ) Draw 1,2 ethandiol c. Trihydroxy have -OH groups ( ) Draw 1,2,3 propantriol

15 Class Used for Functional group Ending Example with name Alcohol Aldehyde Ketone Ethers Organic Acid Esters Amines Amides Classify pages together and Classify pages 46 & 47 for homework

16 C:\Documents and Settings\Barry Smith\My Documents\Chemistry\O Chem Packet 11\L64 - Functional groups.doc Major Understandings ff and hh Unit 7 Lesson Functional Groups Lesson 64 Pre-Assignment Worksheets 29 4 through 29 7 (classify and name) Chapter 22 Q 13, 14, 15, 26, 28, 29, 30, 31, 45, 46, and 69 I. II. Other Organic Compounds Hydrocarbons are only one group of organic compounds. A. Functional Groups the atom or groups of atoms that characterize a family of organic compounds and determines its properties. B. Hydrocarbon Radical all of the hydrogen and carbons not involved in the functional group. (Represented by R - ) Classes A. Alcohol organic compound in which one or more hydrogen atoms has been replaced with a hydroxyl group. (-OH OH - ) They are produced by the process of fermentation. 1. Name using prefixes and change the ending to ol. Must tell where the OH is if it is not on the end. 2. Types a. Monhydroxy alcohols have only 1 OH group 1. Primary carbon with the OH is connected to 1 other C - C OH 2. Secondary carbon with the OH is connected to 2 other C OH C C C 3. Tertiary carbon with the OH is connected to 3 other C C C - C - C OH b. Dihydroxy alcohols has 2 OH groups (glycols or diols) Draw 1,2 ethandiol c. Trihydroxy alchols have 3 OH groups (triols) OH OH OH B. C. -C - C C Glycerine or glycerol or 1,2,3 propanetriol Aldehydes formed by oxidation of primary alcohols 1. functional group C = O (double bonded O on the end) H 2. ending al draw methanal (formaldehyde) Ketones formed by oxidation of secondary alcohols 1. functional group C (double bonded O not on the end) O

17 C:\Documents and Settings\Barry Smith\My Documents\Chemistry\O Chem Packet 11\L64 - Functional groups.doc 2. C- C - C naming a. ending one b. must tell where the double bond is O D. E. F. C C C C C (2 pentanone) Ethers formed by the dehydration of primary alcohols. Not used for anesthesia much anymore due to high flammability and it causes breathing problems and nausea. 1. functional group O 2. Name them by what is before and after the O C O C C (methyl ethyl ether) Draw dimethyl ether (C O C) Organic Acids produced by the oxidation of an aldehyde. Often found in fruits and are very weak. Citric, oxalic acid rhubarb, tartaric grapes. 1. functional group COOH (double bonded O and an OH, always on the end) OH -C = O 2. ending is oic acid Draw propanoic acid Esters produced by the process of esterification. Fats are esters. a. functional group COO (double bonded O and a single O) O G. H. b. Name ends with oate C C O - C (Methyl ethanoate) O Amines - derivatives of ammonia (NH 3 ) so they contain N a. functional group - N- b. Name ends with amine CH 3 CH 2 NH 2 (ethaneamine) Amides - Contain both N and O. a. functional group O Ex. CH 3 CONH 2 - C = O - R - C - NH 2 Assignment #64 Worksheets 30 3 through 30 8 Chapter 23 Q 1, 2, 7, 10 and 49

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24 Name Unit 7 Day 4 Organic Chemistry I. Organic A. - one or more with another element. It occurs in hydrocarbons ( ) when it is a that is substituted. a. Example + + B. Addition Putting on more atoms by a bond. It occurs to compounds. 1. Halogenation table 2. Hydrogenation adding a. Example + C. - when an reacts with an it produces an and a. Example CH 3 COOH + OHC 2 H 5 + D. - breaking down an ( ) in the presence of a strong to produce and. [ ] a. (C 17 H 35 COO) C 17 H 35 COONa E. - breaking down a to produce and. a. Example 2 C 2 H 5 OH + F. (Combustion) burning in the presence of air to produce and. If the combustion is you also get and.

25 a. Example burning of propane. Write equation and balance. + + G. Polymerization making a huge molecule ( ) by bonding many small units ( ) together. 1. Sources 2. Types a. Natural and b. Artificial -,, a. - bonding of monomers by dehydration COOHC 6 H 6 COOH + HOCH 2 CH 2 OH =>COOHC 6 H 6 OCH 2 CH 2 OH + HOH 1,4-benzenedioic acid + 1,2-ethandiol => polyester + water b. - joining monomers by breaking bonds Example n C 2 H 4 (C 2 H 4 ) n H H H H H H H H H H H H C=C + C=C + C=C => :C-C:C-C:C-C: OR -(CH 2 CH 2 ) n - H H H H H H H H H H H H ethylene part of polyethylene H. - breaking down molecular mass into smaller size suitable for use in a. Example C 13 H 28 (l) C 8 H 18 (l) + C 2 H 4 (g) + (g) I. Fractional - separating hydrocarbons using differences in their. The first to boil will be then. Why? Assignment 65 Organic Reactions worksheet and Chapter 23 Q 36ab, 17, 46, and RPE 23 (1 15)

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28 F:\Teachers\BaSmith\Chemistry2005\O Chem Packet 11\Unit 7 review.doc Unit 7 - Organic Chemistry -the study of compounds containing Carbon Properties - most due to covalent bonding (C electroegativity = 2.6) and non-polar molecules (symmetrical) 1. Insoluble in water (water is a polar solvent and organic compounds are generally nonpolar) Likes dissolve like 2. Generally non-electrolytes (they have covalent bonding), even organic acids are weak electrolytes 3. Low melting points (generally non-polar so all they have holding them together is van der Waal forces) 4. React slower than inorganic compounds Bonding - carbon has 4 valence electrons (group 14) so if forms 4 covalent bonds. Unique in it will bond to itself Isomers - compounds that have the same molecular formula but different structural formulas Hydrocarbons - compounds that contain only H and C. Saturated - all single bonds Unsaturated - double or triple bond Homologous series - every hydrocarbon in a series differs from the one before it by 1 C and 2 H ex. C 4H 8 and C 5H 10 Rules for naming (prefixes, suffixes, general formulas, functional groups and examples on Tables P, Q, + R) 1. Find and number the longest Carbon chain and use that prefix (chart P) 2. Check for all single bonds (-ane), double bond (-ene), two double bonds (-diene), triple bond (-yne) or functional group (Table R). Use the proper suffix (tables Q or R) and tell on which C it is located. Ex. 2 Butene 3. Using numbers tell where any halides or alkyl radicals (same as an alkane, but with one less H where it attaches) *If the group appears more than once use the prefix di for 2 and tri for 3. Ex. 2 methyl 3,5 di bromo 6 Octyne Notes - Butane is the first alkane to have isomers and there is no methene or methyne. No multiple bond if only 1 C Benzene Series - hydrocarbon with 6 Carbons in a circle with alternating single and double bonds (resonance) Benzene first member - C 6H 6 Toluene second member - C 7H 8 CH Organic Reactions (Classes can be found on table R) The R in the general formula stands for a hydrocarbon radical (a chain of Carbons with all their H's) 1. Alcohols - fermentation: Sugar zymase Alcohol + Carbon Dioxide 2. Aldehydes - oxidation of primary alcohol (-OH on the end Carbon), so the double bonded O is on the end 3. Ketones - oxidation of secondary alcohol (C with the -OH, is attached to 2 other carbon), so the = O not on end 4. Ethers - dehydration of primary alcohols. Water will be a product as well as the ether 5. Esters - esterification: organic acid + alcohol Ester + water 6. Amines + Amides - contain N, none of the others do 7. Substitution - occurs only to saturated (single bonds) hydrocarbons, usually an H is replaced by a halogen 8. Addition - putting on more atoms by breaking a multiple bond (alkenes or alkynes). The atoms go on the carbon's where the bond broke - C -C - C - C = C - C - + Cl 2 - C -C - C - C - C - C - Cl Cl 9. Combustion (oxidation) - Hydrocarbon + Oxygen Carbon dioxide + water (complete) If it is incomplete, C & CO will be present) Balancing combustion reactions - first balance carbon dioxide, then the water and last the oxygen Cracking - breaking down a higher molecular mass hydrocarbon, into smaller ones suitable for use in gasoline. Fractional Distillation - separating hydrocarbons based on differences in their boiling points mass vdw bp

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