SAS 10 Module 10 Benzene and Its Derivatives PDF

Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: ______________________...

Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ Lesson title: Benzene and its Derivatives Materials: ⚫ Pen and SAS Lesson Objectives: At the end of this module, you should be able References: to: ⚫ General, Organic and 1. Apply the IUPAC and Common nomenclature system for aromatic Biological Chemistry 6th Ed hydrocarbons. (Stoker, 2013) Productivity Tip: Stand up from time to time. The movement, change of perspective, and change in blood flow will help you achieve a bit more. A. LESSON PREVIEW/REVIEW Introduction (2 mins) So far in our previous module we already discussed the three classes of hydrocarbons: Alkanes, Alkenes and Alkynes. In this module we are going to described Benzene and it’s Derivative. More than 150 years ago, organic Chemists realized that another class of hydrocarbons exists, one whose properties are quite different from those of aliphatic hydrocarbons. Because some of these new hydrocarbons have pleasant odors, they were called aromatic compounds. Activity 1: What I Know Chart, part 1 (5 mins) Instructions: In this chart, reflect on what you know now. Do not worry if you are sure or not sure of your answers. This activity simply serves to get you started on thinking about our topic. Answer only the first column, ‘What I Know”. Leave the third column “What I Learned” blank at this time. What I Know Questions: What I Learned (Activity 4) 1. What is the structure of Benzene? 2. How do we name aromatic compounds? 3 What is an Aryl group? This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ B.MAIN LESSON Activity 2: Content Notes (40 mins) Aromatic Hydrocarbons are the third class of unsaturated hydrocarbons; the alkenes and alkynes are the other two classes. Is an unsaturated cyclic hydrocarbon that does not readily undergo addition reaction. Aromatic compound is any compound that has one or more benzene-like rings. We use Arene to describe aromatic hydrocarbons. Arene is a compound containing one or more benzene rings. Aryl group (Ar) is a group derived by removal of an H from an arene. Benzene is the simplest aromatic hydrocarbon, was discovered by Michael Faraday (1791-1867) in 1825. Benzene has the molecular formula C6H6, and has a structural formula that is often formalized as that of a cyclohexatriene-in other words, as a structural formula that involves a six-membered carbon ring in which three double bonds are present. The first structure for benzene was proposed by Friedrich August Kekule in 8172 and a consisted of a six membered ring with alternating single and double bonds, with hydrogen bonded to each other(1). Structure of Benzene Names for Aromatic Hydrocarbons: Depending on the number of substituents attached to benzene ring. Benzene Derivatives with ONE SUBSTITUENT Benzene Derivatives with TWO SUBSTITUENTS Benzene Derivatives with THREE or MORE SUBSTITUENTS Benzene Derivatives with One Substituent: SUBSTITU “benzen ENT Example: e” Ethylbenzene Fluorobenzene Chlorobenzene Propylbenzene This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ Benzene Derivatives with Two Substituents: Prefix System ( ortho( o), meta (m), and para (p) The use of ortho, meta and para in place of position numbers is reserved for disubstituted benzenes. The system is never used with cyclohexanes or other ring system. Ortho- means 1,2 disubstitution; the substituents are on adjacent carbon atoms. Meta- means 1,3 disubstitution; the substituents are one carbon removed from each other. Para- means 1,4 disubstitution; the substituents are two carbons removed from each other (on opposite sides of the ring). When one of the substituents in a disubstituted benzene imparts a special name to the compound( as for example: toluene) the compound is named as a derivative of that parent molecule. The special substituent is assumed to be at ring position 1. When neither substituent group imparts a special name, the substituents are cited in alphabetical order before the ending -benzene. The carbon of the benzene ring bearing the substituent with alphabetical priority becomes carbon 1. Example: 1-Bromo-3-chlorobenzene 1-Chloro-2-ethylbenzne M-Bromochlorobenzene o-Chloroethylbenzene This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ Benzene Derivatives with Three or More Substituents Positions are indicated with numbers Lowest possible numbers for carbon atoms that have substituents If there is a choice of numbering system, then the group that comes first alphabetically is given the lower number. Example: Physical Properties of Aromatic Hydrocarbons Chemical Reactions of Aromatic Hydrocarbons Insoluble in water Alkylation: an alkyl group (R-) from an alkyl chloride (R- Good solvents for other nonpolar C) substitutes for a hydrogen atom on the benzene materials. ring. A catalyst, AlCl3 is needed for alkylation. Is the Less dense than water most important industrial reaction of benzene. Benzene monosubstituted and many disubstituted benzenes are liquids at room temperature Colorless, flammable liquid that burns with a sooty flame In general terms, the alkylation of benzene can be written as: Coal tar was the main source of aromatic hydrocarbons. Petroleum is the main source of such compound. Halogenation(bromination or chlorination): a hydrogen atom on a benzene ring can be replaced by bromine or chlorine if benzene is treated with Br2 or Cl2 in the presence of a catalyst. The catalyst is usually FeBr3 for bromination anf FeCl3 for chlorination. This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ Fused Ring Aromatic Hydrocarbons is an aromatic hydrocarbon whose structure contains two or more rings fused together. The three simplest fused-ring aromatic compounds: A number of fused-ring aromatic hydrocarbons are known to be carcinogen- that is, to cause cancer. Three of the most common potent carcinogens are: Activity 3: Skill-building Activities (with answer key) (30 mins + 5 mins checking) Instructions: Give the common or unique names of the following structures. Write your answer on the space provided. Check your answers against the Keys to Correction found in the last pages of this SAS. Write your Score. Structures Common/Unique name This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ Activity 4: What I Know Chart, part 2 (3 mins) Instructions: To review what was learned from this session, please go back to Activity 1 and answer the “What Learned” column. Notice and reflect on any changes in your answer. This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ Activity 5: Check for Understanding (30 mins) A: Instructions: Assign an IUPAC name to each of the following: Cl 1. CH3-CH-CH2-CH2-CH2-CH3 6. COOH Br 2. CH3-CH-C=CH3 7. Br F 3. CH3-CH-CH2-CH2 8. Cl Cl 4. CH3-CH-CH2-CH2-CH-CH3 9. F CH3 Br 10. Br Br 5. Note: Answers will be provided and discussed by the instructor. C. LESSON WRAP-UP Activity 6: Thinking about learning (5 mins) A. Work Tracker: You are done with this session! Let’s track your progress. Shade the session number you just completed. P1 P2 1 2 3 4 5 6 7 8 9 10 This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ B. Think about your Learning Tell me about your thoughts in this module! What are your insights of this topic? Did you gain new information? FAQs 1. What is the result if toluene is treated with three moles of nitric acid in the presence of sulphuric acid as a catalyst? Ans. It will results in nitration of toluene three times to form the explosive 2,4,6-trinitrotoluene, TNT. The presence of these three nitro groups confers the explosive properties of TNT (1). 2. What is Phenyl? Ans. The aryl group derived by removing a hydrogen atom from benzene. 3. What is polynuclear aromatic hydrocarbon (PAHs?) Ans. Contain two or more benzene rings, with each pair of rings sharing two adjacent carbon atoms. Is a hydrocarbon made up of fused aromatic ring molecules. KEY TO CORRECTIONS for Activity 3: Instructions: Give the common or unique names of the following structures. Write your answer on the space provided. Structures Common/Unique name Aniline Phenol This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ Toluene Anisole Benzoic acid Benzaldehyde ortho-Cresol meta-Cresol para-Cresol Styrene Nitrobenzene meta-Xylene ortho-Xylene This document is the property of PHINMA EDUCATION  Course Code: CHE 026 Student Activity Sheet #10 Name: ____________________________________________________________ Class number: _______ Section: ____________ Schedule: _____________________________________ Date: ______________ para-Xylene This document is the property of PHINMA EDUCATION