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Study Guide for Exam 2

by: Megan steltz

Study Guide for Exam 2 Chem 372-0

Megan steltz
GPA 3.28

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About this Document

This study guide covers chapters 17, 18 and a little bit of 19 i.e. everything that has to do with benzene and a little bit of carboxylic acid.
Organic Chemistry
Gregg M. Wilmes
Study Guide
Organic Chemistry, Benzene, Studyguide, Study Guide
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This 28 page Study Guide was uploaded by Megan steltz on Friday October 14, 2016. The Study Guide belongs to Chem 372-0 at Eastern Michigan University taught by Gregg M. Wilmes in Fall 2016. Since its upload, it has received 12 views. For similar materials see Organic Chemistry in Chemistry at Eastern Michigan University.

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Date Created: 10/14/16
Chapter 17 and 18 Test Study Guide Chapter 17 Outline Comparing aromatic, anti aromatic, and non aromatic compounds o Aromatic compounds o A cyclic, planar, completely conjugated compound that contains 4n + 2 electrons (n = 0, 1, 2, 3…) o An aromatic compound is more stable than a similar acyclic compound that has the same number of π electrons o Anti aromatic compounds o A cyclic, planar, completely conjugated compound that contains 4n π electrons (n = 0, 1, 2, 3…) o An anti aromatic compound is less stable than a similar acyclic compound that has the same number of π electrons o Non aromatic compound o A compound that lacks one (or more ) of the four requirements to be aromatic or antiaromatic Properties of aromatic compounds o Every atom in the ring has a p orbital to delocalize electron density o They are unusually stable. ΔHº for hydrogenation is much less than expected, given the number of degrees of unsaturation o They do not undergo the usual addition reactions of alkenes o ¹H NMR spectra show highly deshielded protons because of ring currents that reinforce the applied magnetic field o All bonding MOs and HOMOs are completely filled and no electrons occupy antibonding orbitals Examples of aromatic compounds with six π electrons Examples of compounds that are not aromatic Practice problems Chapter 17 1) Give the IUPAC name for each compound 2) Draw a structure corresponding to each name a. p-iodoaniline b. 2-phenyl-1-butene c. 2-phenyl-2-propen-1-ol d. m-chlorophenol 3) How many π electrons are contained in each molecule? 4) Which compounds are aromatic for any that are not aromatic tell why it is not? 5) Which of the following heterocycles are aromatic? 6) Label each compound as aromatic, antiaromatic, or not aromatic 7) Hydrocarbon A possesses a significant dipole, even though it is made of only C-C and C-H bonds. Explain why there is a dipole and use resonance structures to show the direction of the dipole. Which ring is more electron rich? 8) a. How many π electrons does C contain? b. How many π electrons are delocalized in the ring? c. Explain why C is aromatic 9) Draw additional resonance structures for each species Chapter 18 Outline Mechanism of Elecrophilic Aromatic Substitution o electrophilic aromatic substitution follows a two-step mechanism. Reaction of the aromatic ring with an electrophile forms a carbocation, and the loss of a proton regenerates the aromatic ring. o The first step is rate determining. o The intermediate carbocation is stabilized by resonance; a minimum of three resonance structures can be drawn. The positive charge is always located ortho or para to the new C-E bond Three Rules Describing the Reactivity and Directing Effects of Common Substituents 1) all ortho, para directors except the halogens activate the benzene ring 2) all meta directors deactivate the benzene ring 3) the halogens deactivate the benzene ring and direct ortho, para Summary of Substituent Effects in Electrophilic Aromatic Substitution Five Examples of Electrophilic Aromatic Substitution 1) Halogenation – Replacement of H by Cl or Br o Polyhalogenation occurs on benzene rings substituted by OH and NH2 ( and related substituents) 2) Nitration- Replacement of H by NO2 3) Sulfonation- Replacement of H by SO3H 4) Friedel-Craft alkylation- Replacement of H by R o Rearrangements can occur o Vinyl halides and aryl halides are unreactive o The reaction does not occur on benzene rings substituted by meta deactivating groups of NH2 groups o Polyalkylation can occur 5) Friedel-Crafts acylation- Replacement of H by RCO o This reaction does not occur on benzene rings substituted by meta deactivating groups or NH2 groups Other reactions of benzene derivatives 1) Benzylic Halogenation 2) Oxidation of alkyl benzenes o A benzylic C-H bond is need for reaction 3) Reduction of ketones to alkyl benzenes 4) Reduction of nitro groups to amino groups Chapter 18 Practice Problems 1) Draw the products formed when Phenol (C6H5OH) is treated with each reagent. a. HNO3, H2SO4 b. CH3CH2Cl, AlCl3 c. product in a. then Sn, HCl d. Cl2, FeCl3 2) Draw the products formed when benzonitrile (C6H5CN) is treated with each reagent. a.Br2, FeBr3 b.SO3, H2SO4 3)Draw the Products formed when each compound is treated with CH3CH2COCl, AlCl3 4) Draw the products of each reaction 4) Explain why the following reaction would not form the given product. The make a synthesis of A from benzene 5) Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution a. C6H5NO2, C6H6, C6H5OH b. C6H6, C6H5Cl, C6H5CHO c. C6H6, C6H5NO2, C6H5NH2 7) Which benzene ring in each compound is more reactive in electrophilic aromatic substitution 8) Draw a stepwise mechanism for the reaction. 9) Synthesize the compound from benzene and any other organic or inorganic reagents. a. m-bromonitrobenzene b. butylbenzene c. o-bromonitrobenzene 10)Synthesize each compound from toluene and any other organic or inorganic reagents. d. C6H5CH2Br e. C6H5CHO 11)Devise a synthesis from phenol and any other organic or inorganic reagent to each compound. Chapter 19 Practice Problems 1) Draw the structure corresponding to each name a. 3,3-dimethylpentanoic acid b. 4-chloro-3-phenylheptanoic acid c. m-hydroxybezoic acid d. potassium acetate 2) Give the IUPAC name for each compound 2) Draw the organic products formed in each reaction Chapter 17 and 18 Test Study Guide  Chapter 17 Outline  Comparing aromatic, anti aromatic, and non aromatic compounds o Aromatic compounds  o A cyclic, planar, completely conjugated compound that contains 4n + 2  electrons (n = 0, 1, 2, 3…) o An aromatic compound is more stable than a similar acyclic compound  that has the same number of π electrons  o Anti aromatic compounds o A cyclic, planar, completely conjugated compound that contains 4n π  electrons (n      = 0, 1, 2, 3…) o An anti aromatic compound is less stable than a similar acyclic compound  that has the same number of π electrons o Non aromatic compound  o A compound that lacks one (or more ) of the four requirements to be  aromatic or anti aromatic  Properties of aromatic compounds  o Every atom in the ring has a p orbital to delocalize electron density o They are unusually stable. ΔHº for hydrogenation is much less than  expected,   given the number of degrees of un saturation  o They do not undergo the usual addition reactions of alkenes  o ¹H NMR spectra show highly deshielded protons because of ring  currents that reinforce the applied magnetic field   o All bonding MOs and HOMOs are completely filled and no electrons  occupy antibonding orbitals  Examples of aromatic compounds with six π electrons  Examples of compounds that are not aromatic   Practice problems Chapter 17  1) Give the IUPAC name for each compound  2) Draw a structure corresponding to each name  a. p­iodoaniline b. 2­phenyl­1­butene c. 2­phenyl­2­propen­1­ol d. m­chlorophenol 3) How many π electrons are contained in each molecule?  4) Which compounds are aromatic for any that are not aromatic tell why it is not?  5) Which of the following heterocycles are aromatic? 6) Label each compound as aromatic, anti aromatic, or not aromatic  7)  Hydrocarbon A possesses a significant dipole, even though it is made of only C­C and C­H bonds. Explain why there is a dipole and use resonance structures to show the  direction of the dipole. Which ring is more electron rich?  8)  a. How many π electrons does C contain? b. How many π electrons are delocalizing in the ring? c. Explain why C is aromatic  9) Draw additional resonance structures for each species  Chapter 18 Outline  Mechanism of Elecrophilic Aromatic Substitution  o electrophilic aromatic substitution follows a two­step mechanism.  Reaction of the aromatic ring with an electrophile forms a carbocation,  and the loss of a proton regenerates the aromatic ring. o The first step is rate determining. o The intermediate carbocation is stabilized by resonance; a minimum of  three resonance structures can be drawn. The positive charge is always  located ortho or para to the new C­E bond Three Rules Describing the Reactivity and Directing Effects of Common Substituents 1) all ortho, para directors except the halogens activate the benzene ring   2) all meta directors deactivate the benzene ring 3) the halogens deactivate the benzene ring and direct ortho, para Summary of Substituent Effects in Electrophilic Aromatic Substitution Five Examples of Electrophilic Aromatic Substitution 1) Halogenation – Replacement of H by Cl or Br o Polyhalogenation occurs on benzene rings substituted by OH and NH2  (  and related substituents) 2) Nitration­ Replacement of H by NO2   3) Sulfonation­ Replacement of H by SO3H 4) Friedel­Craft alkylation­ Replacement of H by R o Rearrangements can occur  o Vinyl halides and aryl halides are unreactive o The reaction does not occur on benzene rings substituted by meta  deactivating groups of NH2 groups o Polyalkylation can occur 5) Friedel­Crafts acylation­ Replacement of H by RCO o This reaction does not occur on benzene rings substituted by meta  deactivating groups or NH2 groups Other reactions of benzene derivatives  1) Benzylic Halogenation  2) Oxidation of alkyl benzenes o A benzylic C­H bond is need for reaction 3) Reduction of ketones to alkyl benzenes 4) Reduction of nitro groups to amino groups Chapter 18 Practice Problems  1) Draw the products formed when Phenol (C6H5OH) is treated with each reagent. a. HNO3, H2SO4 b. CH3CH2Cl, AlCl3 c. product in a. then Sn, HCl d. Cl2, FeCl3 2) Draw the products formed when benzonitrile (C6H5CN) is treated with each  reagent.                                                a.Br2, FeBr3                                                 b.SO3, H2SO4       3)Draw the Products formed when each compound is treated with CH3CH2COCl,  AlCl3 4) Draw the products of each reaction 5) Explain why the following reaction would not form the given product. The  make a synthesis of A from benzene 6) Rank the compounds in each group in order of increasing reactivity in  electophilic aromatic substitution  a. C6H5NO2, C6H6, C6H5OH b. C6H6, C6H5Cl, C6H5CHO c. C6H6, C6H5NO2, C6H5NH2        7) Which benzene ring in each compound is more reactive in electrophilic aromatic  substitution  8) Draw a stepwise mechanism for the reaction. 9) Synthesize the compound from benzene and any other organic or inorganic  reagents. a. m­bromonitrobenzene b. butylbenzene c. o­bromonitrobenzene      10)Synthesize each compound from toluene and any other organic or inorganic  reagents. d. C6H5CH2Br e. C6H5CHO               11)Devise a synthesis from phenol and any other organic or inorganic reagent to  each compound.  Chapter 19 Practice Problems  1) Draw the structure corresponding to each name  a. 3,3­dimethylpentanoic acid b. 4­chloro­3­phenylheptanoic acid c. m­hydroxybezoic acid d. potassium acetate            2) Give the IUPAC name for each compound  3) Draw the organic products formed in each reaction 


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