Houston Community College System Organic Chemistry II 2425 Sample EXAM 2A 16 17 and 18 Cholesterol is a lipid found in the cell membranes of all animal tissues and it is transported in the blood plasma of all animals 1 CHEM 2425 Sample EXAM 2A Chapters 16 18 Directions Please write your correct answer next to each question number in space provided 1 Which of the following would you expect to have the highest boiling point A isopropyl alcohol B t butyl alcohol C diethyl ether D n butanol 2 Which of the following would be the highly miscible with most soluble in water A CH3 CH2 CH2 CH2OH B CH3 CH OH CH2 CH3 C CH3 C CH3 2 CH2OH D CH3 C CH3 2 OH 3 What reagents are typically required to accomplish allylic bromination of an alkene A Br2 HBr B NBS CH2Cl2 C Br2 CCl4 D Br2 FeBr3 4 Which of the following are only meta directing strongly deactivating group s I CH3 II CHO A I and IV III OH B II and IV IV NO2 C I II and III D only IV 5 What is the product of refluxing methylethyl ether with HI in acidic solution A ethanol and methyl iodide C ethanol and methyl alcohol B methanol and ethyl iodide D iodoethane and methanol 6 Which of the following is the electrophile that attacks the aromatic ring during nitration A NO2 B HNO3 C NO3 D NO2 7 Which of the following functional group represents the benzyl group A C6H5O B C6H5 C C6H5CH2 D C6H11CH2 8 Which of the following is bromomethyl ethyl ether A CH3CH2 O CH2Br C CH3 O CH2 CH2 Br B CH3 O CH2Br D CH3CH2 O CH2CH2Br 9 2 Methoxypentane is classified as A a symmetrical ether B a secondary alcohol 2 C an epoxide D an ether 10 The following reaction classifies as R CHO R CH2OH A an oxidation B a reduction C hydration 11 What is the incorrect name for the following compound CH3 B 2 3 epoxy butane D all of these A 1 2 dimethyloxide C 1 2 Dimethylepoxide D tautomerization O CH CH CH3 12 Which reagent s would accomplish the following reaction SO3H A H2O H OH B NaOH H3O C LiAlH4 D CH3MgBr H2O 13 Which of the following reagent s used for alkylation process of benzene A CH3Cl AlCl3 B CH3MgBr ether H2O C MnO4 H2O heat D NBS CCl4 14 Which of the following reagent s provides the following conversion CH CH3 CHO OH A CH3COOH H B MnO4 H2O heat C CH3COCl AlCl3 D none of these 15 What is the product of the following reaction OH PCC A O CHO COOH C B 3 D PART II Nomenclature 20 points a Write the correct IUPAC names OH OCH3 O OH CH2 CH3 OH A B C OCH3 D E A B C D E b Write the correct structures tert butylalcohol 3 isopropyl 1 hexanol ethylmethyldisulfide 3 4 dimethyl 1 pentanol 2 methyltetrahydrofuran 4 PARTT III REACTIONS 20 points What major product s would you expect from the following reactions a HNO3 H2SO4 b SO3 H2SO4 c Cl AlCl3 d Cl Na NH2 NH3 e KMnO4 H2O heat f OH SOCl2 pyridine CH3 g CO CH3 NaBH4 ether H3O NO2 h 2 H3O 1 RCO3H CH2Cl2 1 CH3CH2MgBr ether i CH3 CH2 CHO 2 H2O j 5 PART IV SYNTHESIS 15 points a What is the best procedure for preparing the following compound from benzene requires more than one step OCH3 b Identify the structures for the compounds A C D E and F CH3 Compound A CH3Cl AlCl3 KMnO4 C water heat CH3CH2OH acid E F LiAlH4 reduction D c Illustrate the mechanism for acid catalyzed dehydration of 1 methylcyclohexanol Be sure to use curved arrows electron flow for complete credit 6 Bonus Question 10 points Propose a plausible structure and for a C10H12O compound with the following NMR spectrum Show your work for complete credit 7 CHEM 2425 Sample EXAM 2 Chapters 16 18 Answers Part I Multiple Choice 1 D 6 D 2 D 7 C 3 B 8 A 4 B 9 D 5 A 10 B 11 A 12 B 13 A 14 D 15 D Part II Nomenclature a A 3 3 dimethylpentanol D m dimethoxybenzene b B benzyl alcohol C 3 ethyl 1 2 epoxycylopentane E 2 ethyl 3 methylphenol CH3 CH3 C OH OH CH3 tert butylalcohol CH3CH2 O CH3 2 methyltetrahydrofuran 3 4 dimethyl 1 pentanol Part III Reactions a NO2 b HSO3 HSO4 c Cl NH2 d COOH e CHOH CH3 f g NO2 COOH S CH3 ethylmethyldisulfide 3 isopropyl 1 hexanol OH S CH3 8 h i and O j OH CH3CH2 CH OH OH CH2CH3 OH OH Part IV Synthesis a OCH3 Br 1 NaH 2 CH3Cl ether AlBr3 OH NBS CCl4 1 Hg OAc 2 H2O 2 NaBH4 Br KOH ethanol b COOH COO CH2CH3 CH2OH CH3CH2OH A C D E F c CH3 CH3 OH H HSO4 O H H oxonium ion formation protonation dehydration CH3 tertiary carbocation CH3 HSO4 H2SO4 H Methyl cyclohexene Bonus Question D U C H 2 1 10 12 2 1 5 1 db and benzene ring isobutyrophenone Assign A B C D Shift ppm 7 95 7 67 to 7 31 3 543 1 216 9 Houston Community College System Organic Chemistry II 2425 Sample EXAM 2B 16 17 and 18 10 CHEM 2425 Sample EXAM 2B Chapters 16 17 and 18 Score Part I Multiple choice questions 45 points NAME Directions Please write your correct answer next to each question number in space provided 1 Under what reaction conditions does the electrophilic chlorination of aromatic compounds usually occur A Cl2 AlCl3 B Cl2 H2O C Cl2 CCl4 D NaCl H2O E NaCl CH3OH 2 In electrophilic aromatic substitution reactions the nitro group is A a m director since it destabilizes the meta sigma complex more than the ortho para B a m director since it destabilizes the meta sigma complex less than the ortho para C an o p director since it stabilizes the ortho para sigma complex more than the meta D an o p director since it stabilizes the ortho para sigma complex less than the meta E none of the above 3 Rank the following groups in order of increasing activating power in electrophilic aromatic substitution 11 reactions I OCH3 A I II IV III II OCOCH2CH3 B IV III II I III CH2CH3 C II I IV III IV Br D III I II IV E none of these 4 In electrophilic aromatic substitution reactions a bromine substituent A is a deactivator and a m director B is a deactivator and an o p director C is an activator and a m director D is an activator and an o p director E none of the above 5 Provide the structure of the major mononitration product of the compound below A B C D E two of these 6 In electrophilic aromatic substitution reactions a CO2H substituent on the aromatic ring is A a deactivator and a m director …