Item ID: School: Subject: Organic chemistry Standard: 22.1 Level: advanced Item Type: MC Points: DOK:2 Correct Response: C When a double bond is formed between two atoms, one of the bonds is a sigma bond and the other is a pi bond. The pi bond is created by the overlap of which of the following? A. B. C. D. sp2 hybrid orbitals sp3 hybrid orbitals p orbitals s orbitals Item ID: Standard: 22.2 School: Subject: organic compounds Level: Advanced Previous use: Item Type: MC Points: DOK:2 Correct Response: C Item: to have a cis and trans isomers, a compound must have which of the following? A. sp bonded carbon atoms B. sp3 bonded carbon atoms C. sp2 bonded carbon atoms. D. (A) and (B) Item ID: School: Subject: Organic compounds Standard: 22.3 Item Type: MC Points: Level: advanced chemistry DOK:2 Correct Response: C Which of the following is not related to sereo isomers? A. Require four different substituent’s attached to one carbon atom. B. Have virtually identical physical properties C. Often have the same biological activities D. Are mirror images. Item ID: Standard: 22.4 Item Type: MC School: Subject: aliphatic compounds Points: Level: G12A DOK: 2 Correct Response: D Which statement explains how nucleophilic substitution is initiated in an SN1 mechanism? a. An electrophile approaches the carbon being attached. b. A nucleophile approaches the carbon being attached. c. An electrophile readily detaches from the attached carbon. d. A nucleopile readily detaches from the attached carbon. Item ID: School: Subject: organic reactions Standard: 22.6 Level: advanced chemistry Item Type: MC Points: DOK:2 Correct Response: B What are the products of the following hydrolysis reaction? H3CCOCl +H2O → …………… + …………….. A. CH3CHO +HCl B. CH3COOH+HCl C. CH3CH3 +OH D. CH3CH2OH +HCl Item ID: Standard: 23 - 1 School: Item ID: Standard: 22.5 Subject: Level: G12A School: Subject: ORGANIC What is the name of the following structure? reactions Level:compound advanced chemistry Item Type: MC Points: Item Type: MC DOK: 2 Points: Correct Response: c DOK:2 Correct Response: B In the reaction below which of the following show the Lewis acid and Lewis base? CH3-CH2-CH2Cl + NaOH NaCl + CH3CH2CH2OH A. CH3-CH2-CH2Cl Lewis base , NaOH Lewis acid B. CH3-CH2-CH2Cl Lewis acid , NaOH Lewis base a- 2-benzene-2-chlorobutane C. CH3-CH2-CH2Cl Lewis acid , CH3CH2CH2OH Lewis base b- 2-chloro-2- phenyl pentane D. NaOH Lewis base , NaCl Lewis acid c- 2- chloro-2- phenyl butane d- 3- chloro-3- phenylpentane Item ID: School: Subject: Standard: 23 – 1 Level: G12A What is the name of the following compound ? a- Ester Benzene benzoate b- Ester phenyl benzoate Item Type: MC Points: DOK: 2 Correct Response: b c- Diphenylketone d- Di phenyl methanone Item ID: School: Subject: Standard: 23 – 2 Item Type: MC Points: DOK: 2 Correct Response: c Level: G12A Which of the following compounds can rotate all the bonds? a-ID: C6H6 Item School: b- C6H12 Subject: c- C6H14 d- C6H10 Standard: 23 – 3 Level: G12A Item Type: MC Points: DOK: 2 Correct Response: c Which of the following is the product(s) of nitration of methyl benzene? a- 2-nitromethyl benzene only b- 4- nitromethyl benzene only c- 2-nitrotoluene and 4-nitrotoluen d- 2- nitro toluene and 3-nitrotoluen Item ID: School: Subject: Standard: 23 – 4 Level: G12A Item Type: MC Points: DOK: 2 Correct Response: b Which of the following is true about reaction of benzene with nitric acid in presence of sulphuric acid ? a- The product is benzene sulfonic acid b- The product is nitrobenzene c- The type of reaction is nucleophilic substitution d- The nucleophile is NO2+ ion Item ID: School: Subject: Standard: 23 – 4 Level: G12A Item Type: MC Points: DOK: 2 Correct Response: a What is the effect of delocalization on reaction of benzene? a- Benzene reacts by electrophilic substitution reaction b- Benzene reacts by nucleophilic substitution reaction c- Benzene reacts by addition reaction in all of its reactions d- Benzene can react by elimination reaction Item ID: School: Subject: Standard: 23 – 5 Level: G12A Item Type: MC Points: DOK: 2 Correct Response: d What is the product of the reaction between phenol and dilute nitricacid? a- 2-,3- dinitrophenol b- 2-nitrophenol and 3-nitro phenol c- 2,4-dinitrophenol d- 2-nitrophenol and 4-nitrophenol Item ID: School: Subject: Standard: 23 – 5 Level: G12A Item Type: MC Points: DOK: 2 Correct Response: b Which of the following compounds is the most acidic? a- Cyclohexanol b- Hydroxybenzene c- Cyclohexane d- Aminobenzene Item ID: School: Subject: Standard: 23 – 6 Level: G12A Item Type: MC Points: DOK: 2 Correct Response: b What is the product of the reduction of nitro benzene in presence of HCl and iron? a- Benzoic acid b- Phenyl amine c- Phenol d- Toluene Item ID: School: Subject: Standard: 23 – 7 Level: G12A Item Type: MC Points: DOK: 2 Correct Response: b What is the type of the mechanism of azo (diazo) coupling reaction? a- Nucleophilic aromatic substitution b-Electrophilic aromatic substitution c- Electrophilic addition d- Nucleophilic addition Item ID: School: Standard: 23 – 7 Item Type: MC Points: Subject: Level: G12A DOK: 2 Correct Response: c Which is the main compound can be used for production of azo-dyes? a- Benzaldehyde b- Benzoic acid c- Amino benzene d- Tolouene Item ID: School: Subject: Macromolecules Previous use: Standard: 24.1 Level: Advanced Item Type: MC Points: DOK: Correct Response:D What is the monomer used to form the polymer –[-CH2CHCl-]-n ? A. CH3CH2Cl B. CH CCl C. CHnCHCln D. CH2 = CHCl Item ID: School: Subject: Macromolecules Standard: 24.1 Level: Advanced Item Type: MC Points: DOK:2 Correct Response:C what is the functional group needed for an organic acid to form a peptide bond? A. –C-O-H B. –C=O C. –NH2 D. –CH3 Item ID: School: Subject: organic compounds Standard: 22.1 Level: G12 –A Item Type: CR Points: DOK:2 Complete the following table C2H6 C2H4 Type of hybridization Bond angle C2H6 C2H4 Type of hybridization Sp3 Sp 2 Bond angle 109.5 120 Item ID: Standard: 22.3 Item Type: CR School: Points: Subject: organic compounds Level: G12 –A DOK: 2 Draw the structural formula of each of the four stereo isomers of the following structural formula : CH3CH(OH)CH=CHCH3 CH3CH(OH) CH3 H CH3 C=C C=C H H CH3CH(OH) H H C C CH3CH(OH) OH CH3 CH3 H OH CH3CH(OH) Item ID: School: Subject: organic compounds Standard: 22.3 Level: G12 –A Item Type: CR Points: DOK: 2 1,2dicholro cyclopropane has a cis-trans isomers Explain why this is so, and draw the structure of the two isomers. Answer Due to the restricted movement of the sigma bond in the cyclic structure. Item ID: Standard: 22.4 Item Type: CR School: Points:3 Subject: organic reactions Level: G 12-A DOK: 2 a) When propene reacts with hydrogen + chloride ,initial attack is by H on the pi electrons on the double bond .write the structures of the two possible carbocations formed as a result of this attack. b) c) Which of the carbocations is more stable? Use your answer in (b) to explain why virtually 1-chloropropane is not formed in the reaction of propene with hydrochloric acid. Answer : a) CH3CH2CH2+ OR CH3 CH+CH3 b) there is only one major product. c) This is in line with Markovnikov's Rule which says: When a compound HX is added to an unsymmetrical alkene, the hydrogen becomes attached to the carbon with the most hydrogens attached to it already. In this case, the hydrogen becomes attached to the CH2 group, because the CH2 group has more hydrogens than the CH group. Notice that only the hydrogens directly attached to the carbon atoms at either end of the double bond count. The ones in the CH3 group are totally irrelevant. Item ID: School: Subject: Organic reactions Standard: 22.4 Level: G12 -A Item Type: CR Points: DOK:2 1. Complete the following equation: CH3CH2Br +NH3 ……………….. 2. Write the mechanism of the reaction CH3CH2Br +NH3 CH3CH2NH2 The mechanism involves two steps. The first is a simple nucleophilic substitution reaction: . In the second step of the reaction an ammonia molecule may remove one of the hydrogens on the -NH3+. An ammonium ion is formed, together with a primary amine - in this case, ethylamine. Item ID: Standard: 22.5 Item ID: School: Subject: organic compounds Standard: 22.4 Level: G12 -A Item Type: CR Item Type: CR Points: 3 DOK:2 A. Explain why 1-bromopropane and 2-bromo2-methyl propane undergo nucleophilic substitution at different rates. B. Give examples for this reaction. A. CH2Br-CH2-CH3 Primary haloalkane SN2 mechanism Depends on the rate of both the haloalkane and the nucliophile CH3-C(CH3)Br-CH3 tertiary haloalkane SN1 Mechanism the rate depends on the subtract only B. CH2Br-CH2-CH3 +OH- CH2OH-CH2CH3 CH3-C(CH3)Br-CH3 +OH- CH3-C(CH3)OHCH3 School: Subject: organic compounds Level: G12 -A Points: DOK:2 The reaction C6H6 +HNO3 C6H5NO2 + H2O a) What is the electrophile in this reaction? What is the source of the electrons? b) in terms of Lewis acids and Lewis bases explain the cause of the nitration of benzene in this reaction. a)NO2+ From HNO3 Is the electrophile and the source is the benzene ring b)the benzene ring is a electron pair donor Lewis base and the electrophile is Lewis acid Item ID: School: Subject: Organic reactions Standard: 22.6 Level: G12 -A Item Type: CR Points: DOK:3 Give the formula of two organic compounds that will react together to give each of the following products: I. II. 1. CH3COOCH3 CH3CH2CONH2 Product Reactant (1) Reactant (2) CH3COOCH3 CH3COCl or CH3COOH CH3OH 2. CH3CH2CONH2 Item ID: School: Subject: : CH3 CH2COCl Standard: 23-1 Level: G12 -A NH3 Item Type: CR Points: DOK: 2 Give the name of the following compound. 2,5-dichloro-3-methyl phenol 2,5-dichloro-3-methylhydroxy benzene Item ID: School: Subject: : Standard: 23-1 Level: G12 -A Give the name of the following compound. Item Type: CR Points: DOK: 2 2—phenyl- trans --2-butene Item ID: School: Subject: : Standard: 23-2 Level: G12 -A Item Type: CR Points: DOK: 2 From the diagram above there is a difference between the expected value for the enthalpy change of hydrogenation of kekule- form of benzene ( -360Kjmol-1 ) and the experimental value of hydrogenation of real benzene equal (- 208 Kjmol-1 ) Explain these change in the value of enthalpy? Because the delocalization in benzene ring make it very stable . That make it need more energy to break ; these pi bonds Item ID: School: Subject: : Standard: 23-2 Item Type: CR Points: DOK: 2 Level: G12 -A Complete the following table Ethene Benzene Ethane Ethene Benzene Ethane Type of reaction In standard condition addition Substitution Substitution Shape of molecule Trigonal planer Hexagonal planer Tetrahedral Position of pi bonds. Localize delocalized No pi bond Type of reaction In standard conditions Stability Shape of molecule Position of pi bonds. rotation of C-C bonds rotation of C-C bonds Item ID: School: Subject: Can’t rotate Can’t rotate Standard: 23-3 Level: G12 –A Can rotate Item Type: CR Points: DOK: 3 The products of the reaction between toluene and chlorine is depend on presence of a catalyst or sunlight .Explain that by equations. Item ID: School: Subject: : Standard: 23-3 Level: G12 -A Item Type: CR Points: DOK: 3 In lab how can we distinguish between toluene and benzene using Potassium permanganate .Explain your answer using equation. By adding KMnO4 to both of them in alkali solution it can oxidized the toluene and give benzoic acid the color is change. But with benzene no reaction and the color of KMnO4 is not change Item ID: School: Subject: : Standard: 23-4 Level: G12 -A Item Type: CR Points: DOK: 3 Write the mechanism of nitration of benzene .then answer the following questions a- Identify the electrophile b- What is the source of electron in the reaction? a-Electrophile ion Is : NO2+ b-Benzene ring Item ID: Standard: 23-4 Item Type: CR School: Points: Subject: : Level: G12 -A DOK: 3 Complete the following reaction the answer Questions below: C6H6 + CH3COCl ------------------------- + ------------------------------ a- What is the name given for the major product? b- What is the catalyst used for this reaction? c- What is the electrophile of the reaction? d- Write the mechanism of the reaction? C6H6 + CH3COCl C6H5-COCH3 + HCl a- Phenyl ethanone b- AlCl3 or FeCl3 c- CH3CO+ d- Or methylphenyl ketone Item ID: School: Subject: : Standard: 23-5 Level: G12 –A Item Type: CR Points: DOK: 2 Compare between phenol and cyclohexanol in terms of acidity. Explain your answer. Acidity Phenol Cyclohexanol Weak acid Not acid Because oxygen atom share with one of its lone pair of electrons to benzene ring in delocalization and increase the density of electrons around benzene ring .Easy to lose H+ and form phenoxide ion which is more stable than phenol . Item ID: Standard: 23-5 Item Type: CR School: Points: Subject: : Level: G12 -A DOK: 2 Write equations to represent the following reactions 1- Phenol with sodium metal 2- Phenol with concentrated nitric acid in presence of H2SO4 Item ID: School: Subject: : Standard: 23-6 Level: G12 -A Item Type: CR Points: DOK: 2 Write an equation to prepare phenylamine by the reduction of nitrobenzene Item ID: School: Subject: : Standard: 23-7 Level: G12 -A Explain why azo-dye compounds used in food ? Item Type: CR Points: DOK: 2 Because they are not toxic Item ID: School: Subject: : Standard: 23-7 Level: G12 -A The following equations show the formation of azo-dye. NH2 + HNO2 + HCl below 5°C A nitrous acid OH A+ NaOH B + HCl Write the chemical structure for: a) Compound (A) b) Compound (B) A- + 2H2O Item Type: CR Points: DOK: 3 B- Item ID: School: Subject: : Standard: 23-7 Level: G12 -A Item Type: CR Points: DOK: 3 Using benzene, conc. nitric acid, conc. sulphuric acid, Sn , conc. HCl and phenol. Write an equation to prepare azo-dye. Item ID: School: Subject: : Standard: 24-1 Level: G12 -A Item Type: CR Points: DOK: 2 What are the products of hydrolysis of the following protein? Item ID: School: Subject: : Standard: 24-1 Level: G12 -A State the methods which used to separate protein. 1- Ion-exchange chromatography 2- Electrophoresis 24. Item Type: CR Points: DOK: 2 Item ID: School: Subject: : Standard: 24-1 Level: G12 –A Item Type: CR Points: DOK: 2 Proteins are formed from combinations of 20 different amino acids through peptide bonds .Write an equation to show the formation of this bond? Item ID: School: Subject: macromolecules Standard: 24.1 Level: G12 –A Item Type: CR Points: DOK:2 A. Identify the process that breaks down a protein into its constituent monomers. B. Write the chemical equation for this process. Proteins can be broken down into amino acids from which they are made. This process is called hydrolysis. Hydrolysis is the reverse of condensation as represented in Item ID: School: Subject: macromolecules Standard: 24.4 Level: G12 -A Item Type: CR Points: DOK:2 How are the polymer chains in rubber changed by the vulcanization process? Vulcanization or vulcanisation refers to a specific curing process of rubber involving high heat and the addition of sulfur or other equivalent curatives. It is a chemical process in which polymer molecules are linked to other polymer molecules by atomic bridges composed of sulfur atoms or carbon to carbon bonds. Item ID: School: Subject: : Standard: 24-6 Level: G12 -A Item Type: CR Points: DOK: 2 Explain why, thermoplastics can be remolded but thermosetting cannot be remolded Thermosetting contain cross linking make it hard and can't be remolded Item ID: School: Subject: : Standard: 24-6 Level: G12 -A State the main methods used to prepare polymers? 1- By addition 2- By condensation Item Type: CR Points: DOK: 2