a) b) c) d) e) none of these Organic Chemistry II KEY April 25, 2016
|
|
- Tracy Walton
- 6 years ago
- Views:
Transcription
1 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 1. Tamoxifen is a selective estrogen receptor modulator (SERM) used to treat breast cancer. Which of the following reaction energy diagrams describes the reaction of tamoxifen with 3 +? (ote: Stereoisomers are not shown in the reaction energy diagram) A 3 + Tamoxifen a) b) Energy SM Energy SM Reaction rogress Reaction rogress c) d) Energy Energy SM SM e) none of these Reaction rogress Reaction rogress 1
2 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 2. Match each compound (A-D) with its reaction chemistry in electrophilic aromatic substitutions (EAS) nucleophilic aromatic substitutions (AS) and Benzyne reaction. E I. Reacts in AS II. Reacts in EAS Reacts in Benzyne Does not react in EAS, AS or Benzyne A. 3 C C 3 B. C 3 2 a) A = I, II B = II, III C= III D = I, II, III b) A = I B = I,II, III C= IV D = I, II, III c) A = IV B = II, III C= II, III D = I, II, III d) A = IV B = II, III C= IV D = I, II, III e) A = I B = II, III C= III D = I, II, III 2 C. C 3 D. 2 C Which of the following reaction intermediate(s) is generated the fastest in the reaction below? D BS, h ν a) I & II b) III c) I, II & IV d) I e) I, II, III & IV 4. Which reagent(s) will convert 2-nitro-5-vinylacetophenone to 2,4-diethylaniline? E 2 2-nitro-5-vinylacetophenone I. Zn(g), II. Sn2, 22, K 2, t a) II b) I & II c) I d) III e) IV 2
3 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 5. Methylphenidate (TALI) is a chiral drug sold as a racemic mixture to treat ADD (attention deficit and hyperactivity disorder). Recently, ocalin, the d-isomer (R,R) of methylphenidate was approved by the DA for treating ADD. It has a longer duration of action and is more effective in reducing the symptoms of ADD. Which of the following represents the racemic mixture marketed as TALI? B C 3 Methylphenidate (Ritalin) I C 3 C 3 II C 3 C 3 a) I & II b) I & IV c) III & IV d) II & III e) II & IV III IV 6. The pka values of benzoic acid and phenoxy-substituted benzoic acids have been determined experimentally and are provided below. Based on these pka values (not sigma values), which of the following statements is most consistent with this data? B Acid pka Benzoic acid 4.19 o-phenoxybenzoic acid 3.53 m-phenoxybenzoic acid 3.95 p-phenoxybenzoic acid 4.52 a) henoxy substituents follow a resonance effect, regardless of its position on the ring. b) henoxy substituents follow an inductive effect in the ortho and meta positions and the resonance effect in the para position c) henoxy substituents follow an inductive effect regardless of its position on the ring d) henoxy substituents follow an inductive effect in the meta position and a resonance effect in the ortho and para positions. e) henoxy substituents follow an inductive effect in the ortho position and a resonance effect in the meta and para positions. 7. Starting with benzene, which sequence of reagents could be used to prepare 1-bromo-3-chloro-4- isopropylbenzene? (ote: ther isomers may also form) A I. 1. isopropyl chloride, Al3 2. 2, e3 3. Br2, ebr3 II. 1. 2, e3 2. Br2, ebr3 3. isopropyl chloride, Al3 1. isopropyl chloride, Al3 2. Br2, ebr3 3. 2, e3 1. Br2, ebr3 2. 2, e3 3. isopropyl chloride, Al3 3 a) I & III b) I & II c) II & IV d) I, III & IV e) I, II, III & IV
4 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 8. In a study by Ravichandran and Divakar (J. Molecular Catalysis A: Chemical 109(3) , 1996) it was demonstrated that treatment of (2S, 5R)-menthone with sodium borohydride provided (-) menthol as the major product and (+)-neomenthol as a minor product. Which of the following compounds corresponds to (+)-neomenthol, the minor product of the reaction? C (2S, 5R)-menthone C 3 C 3 C 3 C 3 a) IV b) II c) I d) II & IV e) III 9. Rank the relative rates of reaction (fastest > slowest) of the compounds below with a, 2. D I. II. a) I > II > III > IV b) III > II > IV > I c) III > IV > II > I d) IV > III > II > I e) IV > III > I > II 10. Which of the following statements is true as they relate to compound A below? E I. Donation of a results in formation of a conjugate base that contains a new aromatic system that includes rings A and B. II. The pka values of a, b and c are approximately equal. The conjugate base that is generated by donation of c has 6 π electrons associated with its aromatic system. Compound A is aromatic. a A B C c Compound A b a) I b) I & II c) II, III & IV d) III & IV e) III 4
5 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 11. Cinnamic acid (I) and a series of substituted cinnamic acid compounds (II-IV) have been evaluated for activity in inhibiting the generation of glucose in the body. The relative potency of these compounds has been determined and is summarized below. Based on this data, what would be the predicted potency of m-chlorocinnamic acid (m-)? B (most potent) TECY III > I > II > IV (least potent) cinnamic acid C 3 a) III > I > II > IV> m- b) III > I > II >m- > IV c) III > m- > I > II > IV d) III > I >m- > II > IV e) m- > III > I > II > IV 3 C C 12. Treatment of cuminaldehyde with excess KMn4 will provide: C a) b) e) cuminaldehyde c) d) 13. The major product(s) that would form in the monoalkylation reaction of ortho-dimethoxybenzene, tertbutyl alcohol and acetic acid is (are): A I. 5-tert-butyl-1,3-dimethoxybenzene a) II & V II. 1-tert-butyl-3,4-dimethoxybenzene b) II 4-tert-butyl-1,5-dimethoxybenzene c) III 2-tert-butyl-1,3-dimethoxybenzene d) IV & V V. 1-tert-butyl-2,3-dimethoxybenzene e) I & II 5
6 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 14. The major product(s) of the reaction below is (are): D 2 1 equivalent 2, e3 a) II b) I & V c) III d) I e) I, IV & V I. 2 II V Rank the relative rate of the reaction of each of the compounds below with 34 from fastest to slowest (fastest>slowest). D a) I > II > III > IV b) IV > III > II > I c) IV = II > III > I d) IV > II > III > I e) II > IV > III > I 6
7 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 16. Which of the following conjugate acids of tenofovir has the lowest pka? B Tenofovir (VIREAD) 2 a) b) 2 c) 2 d) 2 3 e) Sigma values may be used to predict the relative pka values of aniline functional groups. Match the proper sigma values to the substituents labeled at carbons A, B, C and D in the compound provided below. E 2 A B C D a) A = ethyl B = acetamido C = acetamido D = amino b) A = ethyl B = amino C = acetyl D = amino c) A = amino B = amino C= acetyl D = amino d) A = amino B = acetamido C = acetyl D = amino e) A = ethyl B = acetamido C = acetyl D = amino 18. Rank the relative rates of formation of products from fastest to slowest (fastest>slowest) in the series of reactions below. C I. 1. 2, e 3 2. S 3, 2 S 4 II. 1., Al 3 2. S 3, 2 S 4 a) II > III > I b) III > II > I c) I > II > III d) II > I > III e) III > I > II 1. 3, 2 S 4 2. S 3, 2 S 4 7
8 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 19. The compound below can be prepared through an intramolecular benzyne reaction. In this reaction, benzyne is generated with base, and the benzyne intermediate then reacts with an electrophile and nucleophile within the same molecule to give this product. Which of the following starting materials could be used to prepare the compound below through an intramolecular benzyne reaction? C I. II. 2 2 a) I b) II & IV c) I & III d) III e) I, II, III & IV Identify A, B and C in the reaction scheme below. E 1., Al3 2, t A X Zn (g), B I. 2. 3, 2 S 4 2, 2 K C a) A = III B = III C = I b) A = IV B = II C = I c) A = V B = III C = II d) A = III B = I C =III e) A = III B = II C = I 2 II. 2 V
9 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 21. Which of the following structures represents a reaction intermediate that is generate upon reaction of para-fluorobenzaldehyde with sodium phenoxide? A a + Sodium henoxide a) II b) II & IV c) III d) I e) IV 22. Which of the following statements most accurately describes the structure below? B G A Atvorvastatin (LIITR) C 2 a) I & IV b) I c) I & III d) I, II & III e) II & III G B G C I. The compound contains one para-substituted ring. II. Ring C contains two activating groups. Reaction with 2, e3 will occur predominantly on ring C. The compound contains an ionizable functional group on ring A. 9
10 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 23. Which of the following compounds is prochiral in a reaction with excess ab4, C3? D Ibudilast Citrol a) I b) I, II & III c) I, III &IV d) I & III e) I, II, III & IV ethidine S Raloxifene C Rank the following phenols from strongest acid to weakest acid. (Use the B phenol for structure III) E C 3 2 Triclosan Eugenol a) III > II > I > IV b) II > I > IV > III c) II > IV> I > III d) III > IV > I > II e) III > I > IV > II A B Tolcapone Albuterol 25. The major product(s) in the reaction of 4-fluoro-2-nitrotoluene with a2, 3 is (are): C I. 3-methyl-2-nitroaniline II. 4-methyl-3-nitroaniline 3-methyl-4-nitroaniline 5-fluoro-2-methyl-3-nitroaniline a) IV b) I & II c) II d) II & III e) I, II & III 10
11 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B Substituent Abbreviation σ meta σpara acetamido- Ac acetoxy- Ac acetyl- Ac alkenyl- -C2=C amino bromo- Br tert-butyl- (C3)3C chloro cyano- C ethoxy- Et ethyl- Et fluoro hydrogen hydroxy methoxy- Me methyl- Me nitro phenoxy- h phenyl- h trifluoromethyl 3C trimethylamino- (C3) Table 1: σ values for Various Substituents 11
12 rganic Chemistry II KEY April 25, 2016 Exam 3: VERSI B 12
Organic Chemistry II A KEY February 24, 2011
rganic Chemistry II A KEY ebruary 24, 2011 Exam 1: VERI A 1. Which of the following reagent(s) (or set of reagents) could react with atorvastatin (LIPITR) as starting material? D or E Atvorvastatin (LIPITR)
More informationOrganic Chemistry II KEY March 27, Which of the following reaction intermediates will form the fastest in the reaction below?
rganic Chemistry II KEY March 27, 2013 Exam 2: VERSI D 1. Which of the following reaction intermediates will form the fastest in the reaction below? C 1 equiv a 2 a) IV b) III c) II d) II & III e) I I.
More informationOrganic Chemistry II KEY March 27, 2013
rganic Chemistry II KEY March 27, 2013 Exam 2: VERSI C 1. Rank the dienophiles from most reactive to least reactive in the Diels Alder reaction (most>least) E I II III IV > II > III > IV b) III > I > II
More informationOrganic Chemistry II KEY March 25, a) I only b) II only c) II & III d) III & IV e) I, II, III & IV
rganic Chemistry II KEY March 25, 2015 Exam 2: VERSIN A 1. Which of the following compounds will give rise to an aromatic conjugate base? E a) I only b) II only c) II & III d) III & IV e) I, II, III &
More informationCHEM Chapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution (homework) W
CHEM 2425. Chapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution (homework) W Short Answer Exhibit 16-1 MATCH a structure or term from the following list with each description below. Place
More informationLecture Topics: I. Electrophilic Aromatic Substitution (EAS)
Reactions of Aromatic Compounds Reading: Wade chapter 17, sections 17-1- 17-15 Study Problems: 17-44, 17-46, 17-47, 17-48, 17-51, 17-52, 17-53, 17-59, 17-61 Key Concepts and Skills: Predict and propose
More informationChapter 17 Reactions of Aromatic Compounds. Electrophilic Aromatic Substitution
Chapter 17 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Electrophile substitutes for a hydrogen on the benzene ring. Chapter 17: Aromatics 2-Reactions Slide 17-2 1 Mechanism Step
More informationChapter 17 Reactions of Aromatic Compounds
rganic Chemistry, 6 th Edition L. G. Wade, Jr. Chapter 17 Reactions of Aromatic Compounds Jo Blackburn Richland College, Dallas, TX Dallas County Community College District 2006, Prentice all Electrophilic
More informationOrganic Chemistry II KEY February 20, 2013
rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 1. Which of the following compounds could be generated from reaction of Z 3,4 dimethyl 2 pentene with m chloroperbenzoic acid? E C 3 3 C 3 C C
More informationREACTIONS OF AROMATIC COMPOUNDS
A STUDENT SHOULD BE ABLE TO: REACTIONS OF AROMATIC COMPOUNDS 1. Predict the product(s) of Electrophilic aromatic substitution (EAS): halogenation, sulfonation, nitration, Friedel- Crafts alkylation and
More informationChem 263 Oct. 4, 2016
Chem 263 ct. 4, 2016 ow to determine position and reactivity: Examples The strongest donating group wins: 2 3 2 S 4 + 3 2 2 S 4 2 2 + 2 2 3 2 S 4 2 2 2 2,4,6-trinitrophenol picric acid This reactivity
More informationOrganic Chemistry CHM 224
rganic Chemistry CM 224 Final Exam Review Questions This is a compilation example final exam questions. Provide IUPAC names for each of the structures below. 2 ! Propose a structure for the compound that
More information432 CHAPTER 19. Solutions H H H. Base H O H S O H - SO 3 O S O O O
432 CAPTER 19 Solutions 19.1. Base 19.2. S S - S 3 S S S CAPTER 19 433 19.3. D S D S 3 D D D D D 19.4. S - 2 nitronium ion 2 2 2 2 19.5. c) + 434 CAPTER 19 19.6. Al 3 Al 3 Al 3 Al 3 Al 3 Al 3 CAPTER 19
More informationWilliam H. Brown & Christopher S. Foote
William. Brown & Christopher S. Foote Requests for permission to make copies of any part of the work should be mailed to:permissions Department, arcourt Brace & Company, 6277 Sea arbor Drive, Orlando,
More informationNO 2 O NH 2. Br Br. Br CF 3
1. Rank the following compounds in the trend requested. (15 points each) a. Rank by energy of the lowest unoccupied molecular orbital (LUM). The molecule with the LUM that is lowest in energy is 1, while
More informationIsomerism CH 4 C 2 H 6 C 3 H 8 C 4 H 10 C 5 H 12. Constitutional isomers...
Isomerism 4 2 6 3 8 4 10 5 12 onstitutional isomers... 3 8 Positional isomers... Functional isomers... ow many constitutional isomers are there for the formula 4 8? arbon atoms are often classified as
More informationOrganic Chemistry. Second Edition. Chapter 19 Aromatic Substitution Reactions. David Klein. Klein, Organic Chemistry 2e
Organic Chemistry Second Edition David Klein Chapter 19 Aromatic Substitution Reactions Copyright 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e 19.1 Introduction to Electrophilic
More information2. Which of the following is NOT an electrophile in an electrophilic aromatic substitution reaction? A) NO 2
Name: CHEM 226 Practice Quiz 3 Chapter 4-Aromatic Compounds and Chapter 7- Alcohols, Phenols and Thiols Attempt all questions showing your answers and work clearly for full and partial credits 1. Which
More informationOH OH OH CH 2 CH 2 C(CH 3 ) 2 (a) CH 3 CHCH 2 CHCH(CH 3 ) 2. (b)
hem 226 Problem Set #8 Fundamentals of rganic hemistry, 4 th edition, John McMurry. hapter 8 1. Give IUPA names for the following alcohols. 2 2 ( 3 ) 2 3 2 ( 3 ) 2 Longest chain = 6 carbons:...hexanediol.
More informationORGANIC - BROWN 8E CH. 22- REACTIONS OF BENZENE AND ITS DERIVATIVES
!! www.clutchprep.com CONCEPT: ELECTROPHILIC AROMATIC SUBSTITUTION GENERAL MECHANISM Benzene reacts with very few reagents. It DOES NOT undergo typical addition reactions. Why? If we can get benzene to
More informationNitration of (Trifluoromethyl( Trifluoromethyl)benzene CF 3 HNO 3 + +
Effect on Rate Rate and Regioselectivity in Electrophilic Aromatic Substitution A substituent already present on the ring affects both the rate and regioselectivity of electrophilic aromatic substitution.
More informationOrganic Chemistry II KEY February 22, 2016
rganic hemistry II KEY February 22, 2016 Exam 1: VERSI B 1. Match the reaction energy diagrams to each of the reactions given below. E (Assume no rearrangements occur in any reactions) REATIS I. 1-methylcyclopentanol
More informationChapter 17. Reactions of Aromatic Compounds
Chapter 17 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Although benzene s pi electrons are in a stable aromatic system, they are available to attack a strong electrophile to give
More informationOCH 2 CH 3. A) 2-chlorohexyl ethanoate C) ethyl 2-chlorohexanoate B) 1-chlorohexyl ethanoate D) ethyl 1-chlorohexanoate
(2 points each) Write your answer in the box to the right of the question. 1. A mixture of 1-hexanol and hexanoic acid in diethyl ether is shaken with an aqueous sodium bicarbonate solution. Which line
More informationOrganic Chemistry II KEY February 22, 2016
rganic hemistry II KEY February 22, 2016 Exam 1: VERSI A 1. Tramadol is a drug that is used to treat moderate to severe pain. It contains two chiral centers and is sold as a racemic mixture. Both of the
More informationChemistry Final Examinations Summer 2006 answers
Chemistry 235 - Final Examinations Summer 2006 answers A GEERAL CEMISTRY answers are given from 1-20: no reaction C 3 CC 3 Ph C C C C C 3 Et 2 2 2 B. REACTIS AD REAGETS [32 MARKS] 2. A single substance
More information12/27/2010. Chapter 15 Reactions of Aromatic Compounds
Chapter 15 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Arene (Ar-H) is the generic term for an aromatic hydrocarbon The aryl group (Ar) is derived by removal of a hydrogen atom
More informationChapter 15 Reactions of Aromatic Compounds
Chapter 15 1 Chapter 15 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Arene (Ar-H) is the generic term for an aromatic hydrocarbon The aryl group (Ar) is derived by removal of a hydrogen
More informationChem 263 Oct. 6, Single bonds, σ. e - donating Activate Activate ortho and para directing ortho and para directing
Chem 263 ct. 6, 2009 lectrophilic Substitution of Substituted Benzenes Resonance ffect Inductive ffect C=C, π system Single bonds, σ Strong Weak e - donating Activate Activate ortho and para directing
More informationCHAPTER 16 - CHEMISTRY OF BENZENE: ELECTROPHILIC AROMATIC SUBSTITUTION
CAPTR 16 - CMISTRY F BNZN: LCTRPILIC ARMATIC SUBSTITUTIN As stated in the previous chapter, benzene and other aromatic rings do not undergo electrophilic addition reactions of the simple alkenes but rather
More informationCHEM 347 Organic Chemistry II (for Majors) Instructor: Paul J. Bracher. Quiz # 4. Due in Monsanto Hall 103 by: Friday, April 4 th, 2014, 7:00 p.m.
CHEM 347 Quiz # 4 Spring 2014 Page 1 of 9 CHEM 347 Organic Chemistry II (for Majors) Instructor: Paul J. Bracher Quiz # 4 Due in Monsanto Hall 103 by: Friday, April 4 th, 2014, 7:00 p.m. Student Name (Printed)
More informationPhenols, Ethers, and Organic Sulfur Compound
Phenols, Ethers, and rganic Sulfur Compound Phenols - Structure General Structure - A hydroxy () group attached directly to an aromatic ring: Phenol α-naphthol β-naphthol Note: C2 is not a phenol. Phenols
More informationChem 263 Oct. 10, The strongest donating group determines where new substituents are introduced.
Chem 263 ct. 10, 2013 The strongest donating group determines where new substituents are introduced. N 2 N 3 2 S 4 + N 3 N 2 2 S 4 N 2 N 2 + 2 N N 2 N 3 2 S 4 N 2 2 N N 2 2,4,6-trinitrophenol picric acid
More informationChemistry 52 Exam #1. Name: 22 January This exam has six (6) questions, two cover pages, six pages, and 2 scratch pages.
Chemistry 52 Exam #1 Name: 22 January 2003 This exam has six (6) questions, two cover pages, six pages, and 2 scratch pages. Please check before beginning to make sure no questions are missing. 65 minutes
More informationOrganic Chemistry, 7 L. G. Wade, Jr. Chapter , Prentice Hall
Organic Chemistry, 7 th Edition L. G. Wade, Jr. Chapter 17 Reactions of Aromatic Compounds 2010, Prentice Hall Electrophilic Aromatic Substitution Although h benzene s pi electrons are in a stable aromatic
More informationChapter 5. Aromatic Compounds
Chapter 5. Aromatic Compounds 5.1 Structure of Benzene: The Kekule Proposal Mid-1800s, benzene was known to have the molecular formula C 6 6. Benzene reacts with 2 in the presence of iron to give substitution
More informationChemistry 2050 Introduction to Organic Chemistry Fall Semester 2011 Dr. Rainer Glaser
Chemistry 2050 Introduction to Organic Chemistry Fall Semester 2011 Dr. Rainer Glaser Examination #2 Practice Edition Arenes, Stereochemistry, and Organic Halogen Compounds, with Nucleophilic Substitution
More informationElectrophilic Aromatic Substitution: Direction
Electrophilic Aromatic Substitution: Direction or each of the following species, show the most likely site(s) for electrophilic aromatic substitution, and predict whether the molecule reacts with electrophiles
More informationReactions of Aromatic Compounds
2-1 Reactions of Aromatic Compounds 15.1 2-2 lectrophilic Aromatic Substitution Reactions Aromatic hydrocarbons (= arenes) undergo a substitution reaction with electrophiles: + catalyst + xample: omination
More informationCHEM1902/ N-8 November Consider the following reaction sequences beginning with the carboxylic acid, E.
CEM1902/4 2014--8 ovember 2014 Consider the following reaction sequences beginning with the carboxylic acid, E. 6 ame compounds E and G. E: propionic acid G: methyl propionate Propose structures for compounds
More informationCHEM 240: Survey of Organic Chemistry at North Dakota State University Midterm Exam 02 - Tue, 23 Sep 2014!! Name:! KEY!
CEM 240: Survey of rganic Chemistry at orth Dakota State University Midterm Exam 02 - Tue, 23 Sep 2014!! ame:! KEY! Please read through each question carefully and answer in the spaces provided. A good
More informationExam (6 pts) Show which starting materials are used to produce the following Diels-Alder products:
Exam 1 Name CHEM 212 1. (18 pts) Complete the following chemical reactions showing all major organic products; illustrate proper stereochemistry where appropriate. If no reaction occurs, indicate NR :
More informationb.(12) Where is pyrrole protonated under strong acidic conditions? Why this site of protonation?
1. Rank the following compounds in the trend requested. (15 points each) a. Rank the following dienes by rate of Diels-Alder reaction. The diene which reacts the fastest with an alkene is 1, while the
More informationChapter 17: Reactions of Aromatic Compounds
1 Chapter 17: Reactions of Aromatic Compounds I. Introduction to Electrophilic Aromatic Substitution (EAS) A. General Mechanism II. Reactions of Electrophilic Aromatic Substitution A. Halogenation (E =
More informationSection Practice Exam II Solutions
Paul Bracher Chem 30 Section 7 Section Practice Exam II s Whether problems old r problems new, You d better practice, r you ll fail exam II. -- Anonymous TF Problem 1 a) Rank the following series of electrophiles
More informationChapter 19: Benzene and Aromatic Substitution Reactions [Sections: 18.2, 18.6; ]
Chapter 19: Benzene and Aromatic Substitution eactions [Sections: 18.2, 18.6; 19.1-19.12] omenclature of Substituted Benzenes i. Monosubstituted Benzenes C 2 C 3 ii. Disubstituted Benzenes X X X Y Y Y
More informationChemistry 2030 Survey of Organic Chemistry Fall Semester 2015 Dr. Rainer Glaser
Chemistry 2030 Survey of Organic Chemistry Fall Semester 2015 Dr. Rainer Glaser Examination #2 Reactions of Alkenes & Alkynes, Chemistry of Aromatic Compounds, and Stereochemistry Thursday, October 8,
More informationand Stereochemistry) PAPER 1: ORGANIC CHEMISTRY- I (Nature of Bonding and Stereochemistry) MODULE 4: Applications of Electronic Effects
Subject Chemistry Paper No and Title Module No and Title Module Tag Paper 1: ORGANIC - I (Nature of Bonding Module 4: Applications of Electronic Effects CHE_P1_M4 PAPER 1: ORGANIC - I (Nature of Bonding
More informationCh 16 Electrophilic Aromatic Substitution
Ch 16 Electrophilic Aromatic Substitution Mechanism - Aromatic rings typically undergo substitution, where an H is replaced with an electrophile (E+). - The rings do not typically undergo addition across
More informationElectrophilic Aromatic Substitution
Chem 263 ct. 8, 2013 lectrophilic Aromatic Substitution Benzene appears to be a remarkably stable and unreactive compared to alkenes, such as cyclohexene or ethylene, or even alkanes, such as cyclohexane
More informationChem 261 Dec 6, 2017
209 Chem 261 Dec 6, 2017 REVIEW: Example: K!! + 3 C + 3 C K tert-butoxide (an alkoxide) methanol tert-butanol pka = 16 pka = 19 methoxide stronger base stronger acid (lower pka, more acidic) weaker acid
More informationReactions of Aromatic Compounds. Aromatic compounds do not react like other alkenes. With an appropriate catalyst, however, benzene will react
Reactions of Aromatic Compounds Aromatic compounds do not react like other alkenes 2 Fe 3 2 Does not form A major part of the problem for this reaction is the product has lost all aromatic stabilization,
More informationChemistry 2030 Survey of Organic Chemistry Fall Semester 2015 Dr. Rainer Glaser
Chemistry 2030 Survey of Organic Chemistry Fall Semester 2015 Dr. Rainer Glaser Examination #2 Reactions of Alkenes & Alkynes, Chemistry of Aromatic Compounds, and Stereochemistry Thursday, October 8,
More informationCHEM J-8 June Complete the following table. Make sure you give the name of the starting material where indicated. REAGENTS/ CONDITIONS
CEM1102 2014-J-8 June 2014 Complete the following table. Make sure you give the name of the starting material where indicated. STARTIG MATERIAL REAGETS/ CDITIS STRUCTURAL FRMULA(S) F MAJR RGAIC PRDUCT(S)
More informationNBS, CCl 4 heat A B C D
1. What is(are) the expected product(s) of the following reaction? 2 C=CC( ) 2 NBS, CCl 4 heat A B C D 1) only B 2) only C 3) A and C 4) B and D 2. Which of the following is the 1,4-addition product in
More informationDAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 8 Dr Ali El-Agamey Nomenclature of Benzene Derivatives Nomenclature of Benzene Derivatives To name a benzene ring with one substituent, name
More informationBenzenes & Aromatic Compounds
Benzenes & Aromatic Compounds 1 Structure of Benzene H H C C C H C 6 H 6 H C C C H H A cyclic conjugate molecule Benzene is a colourless odourless liquid, boiling at 80 o C and melting at 5 o C. It is
More informationBENZENE & AROMATIC COMPOUNDS
BENZENE & AROMATIC COMPOUNDS Dr. Zainab M Almarhoon 2 Learning Objectives By the end of chapter four the students will: Understand the resonance description of structure of benzene Understand the hybridization
More informationCh.16 Chemistry of Benzene: Electrophilic Aromatic Substitution
Ch.16 Chemistry of Benzene: Electrophilic Aromatic Substitution Electrophilic aromatic substitution: E + E + + Some electrophilic aromatic substitution: X N 2 S 3 R C R alogenation Nitration Sulfonation
More informationExamples of Substituted Benzenes
Organic Chemistry 5 th Edition Paula Yurkanis Bruice Examples of Substituted Benzenes Chapter 15 Reactions of Substituted Benzenes Irene Lee Case Western Reserve University Cleveland, OH 2007, Prentice
More informationAMINES. 4. From your knowledge of the effects involved, predict or explain experimental results. Important areas include:
AMINES A STUDENT SHOULD BE ABLE TO: 1. Give the IUPAC or common name given the structure, and draw the structure given the name of amines and common nitrogen heterocycles (pyrrole, pyridine, purine, pyrimidine,
More informationChemistry 2030 Survey of Organic Chemistry Fall Semester 2017 Dr. Rainer Glaser
Chemistry 2030 Survey of Organic Chemistry Fall Semester 2017 Dr. Rainer Glaser Examination #2 Reactions of Alkenes & Alkynes, Chemistry of Aromatic Compounds, and Stereochemistry Thursday, October 5,
More informationCHEM 2312 practice final. Version - II
EM 2312 practice final Version - II The following standardized final examination covers the entire introductory year of organic chemistry (EM 2311 and 2312 at Georgia Tech). The exam consists of 70 multiple
More information16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 7 th edition
16. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry, 7 th edition Substitution Reactions of Benzene and Its Derivatives Benzene is aromatic: a cyclic conjugated
More informationAromatic Compounds II
2302272 Org Chem II Part I Lecture 2 Aromatic Compounds II Instructor: Dr. Tanatorn Khotavivattana E-mail: tanatorn.k@chula.ac.th Recommended Textbook: Chapter 17 in Organic Chemistry, 8 th Edition, L.
More informationChapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Reactivity of Benzene
hapter 16 hemistry of Benzene: Electrophilic Aromatic Substitution Reactivity of Benzene - stabilization due to aromaticity makes benzene significantly less reactive than isolated alkenes 2 no reaction
More informationA. B. C. D. 2. Which compound does not give a stable Grignard reagent when reacting with Mg metal?
Practice Test, Chemistry 2220 Final Exam 1. Which structure has the MST signals for its proton NMR? 2. Which compound does not give a stable Grignard reagent when reacting with Mg metal? 3. Which of these
More informationLecture 27 Organic Chemistry 1
CHEM 232 rganic Chemistry I at Chicago Lecture 27 rganic Chemistry 1 Professor Duncan Wardrop April 20, 2010 1 Self Test Question Nitrosonium (not nitronium) cations can be generated by treating sodium
More informationChem 263 Oct. 12, 2010
Chem 263 ct. 12, 2010 Alkyl Side Chain xidation Reaction If the carbon directly attached to the aromatic ring has > 1 hydrogen attached to it, it can be oxidized to the corresponding carboxylic acid with
More informationAllylic and Benzylic Reactivity
17 17 Allylic and Benzylic Reactivity An allylic group is a group on a carbon adjacent to a double bond. A benzylic group is a group on a carbon adjacent to a benzene ring or substituted benzene ring.
More informationChapter 16: Aromatic Compounds
Chamras Chemistry 106 Lecture otes xamination 2 Materials Chapter 16: Aromatic Compounds Benzene, the Most Commonly Known Aromatic Compound: The aromatic nature of benzene stabilizes it 36 kcal.mol 1.
More informationPhysical Organic Chemistry (15 h)
Course code : CEM 43244 Course title : Advanced rganic Chemistry I Physical rganic Chemistry (15 h) Dr. Dinesh Pandithavidana E-mail: dinesh@kln.ac.lk Mobile: 0777-745-720 ffice: B1 222/3 Stereochemical
More informationThe following exam contains 30 questions valued at 3 point/question and bonus opportunities. Name:
Chemistry 261 Exam 3 all 2017 The following exam contains 30 questions valued at 3 point/question and bonus opportunities Name: ELECTROPILIC ADDITION REACTIONS BASIC REACTION OUTCOMES 1. Addition of hydrogen
More informationCHE1502. Tutorial letter 201/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry CHE1502/201/1/2016
CE1502/201/1/2016 Tutorial letter 201/1/2016 General Chemistry 1B CE1502 Semester 1 Department of Chemistry This tutorial letter contains the answers to the questions in assignment 1. FIRST SEMESTER: KEY
More informationB. (3 pts) The following values are independent of the operating frequency of the NMR: a. Coupling constant; c. Chemical shift; b. Gyromagnetic ratio;
CEMISTRY 314-01 MIDTERM # 1 answer key September 29, 2009 Statistics: Average: 70 pts (70%); ighest: 96 pts (96%); Lowest: 37 pts (37%) Number of students performing at or above average: 16 (57%) Number
More information1. Which of the following reactions would have the smallest energy of activation?.
Name: Date: 1. Which of the following reactions would have the smallest energy of activation?. A) +. +. B) + +. C) +.. + D) +.. + E) +.. + 2. Which of the following reactions would have the smallest energy
More informationElectrophilic Aromatic Substitution
Chem 263 Sept 29, 2016 lectrophilic Aromatic Substitution Benzene appears to be a remarkably stable (36 kcal/mole more) and unreactive compared to alkenes, such as cyclohexene or ethylene, or even alkanes,
More information1. CONCEPTS IN ORGANIC CHEMISTRY 2. SYNTHETIC ORGANIC CHEMISTRY 3. ISOMERISM II 4. HYDROCARBONS II 5. HALOALKANES. Vikasana - CET 2012
CET OBJECTIVE QUESTION ON 1. CONCEPTS IN ORGANIC CHEMISTRY 2. SYNTHETIC ORGANIC CHEMISTRY 3. ISOMERISM II 4. HYDROCARBONS II 5. HALOALKANES 1.The inductive effect a. Implies the atoms ability to cause
More informationChapter 13 Reactions of Arenes Electrophilic Aromatic Substitution
. 13 hapter 13 eactions of Arenes lectrophilic Aromatic ubstitution lectrophiles add to aromatic rings in a fashion somewhat similar to the addition of electrophiles to alkenes. ecall: 3 4 Y 1 4 2 1 δ
More information1. CONCEPTS IN ORGANIC CHEMISTRY 2. SYNTHETIC ORGANIC CHEMISTRY 3. ISOMERISM II 4. HYDROCARBONS II 5. HALOALKANES. Vikasana - CET 2012
CET OBJECTIVE QUESTION ON 1. CONCEPTS IN ORGANIC CHEMISTRY 2. SYNTHETIC ORGANIC CHEMISTRY 3. ISOMERISM II 4. HYDROCARBONS II 5. HALOALKANES 1.The inductive effect a. Implies the atoms ability to cause
More informationProblem Set #3 Solutions
Problem Set #3 Solutions 1. a) C 3 (methyl group) Since carbon (E = 2.5) is slightly more electronegative than hydrogen (E = 2.2), there will be a small dipole moment pulling electron density away from
More informationChapter 12. Reactions of Arenes: Electrophilic Aromatic Substitution. Class Notes. A. The method by which substituted benzenes are synthesized
Chapter 12 Reactions of Arenes: Electrophilic Aromatic Substitution Chapter 12 suggested problems: 22, 23, 26, 27, 32, 33 Class Notes I. Electrophilic aromatic substitution reactions A. The method by which
More information(CH 3 ) 3 COH. CH 3 ONa
1. Rank the following compounds in the trend requested. (15 points each) a. Rank by nucleophilicity. The strongest nucleophile is 1, while the weakest nucleophile is 5. C 3 PNa (C 3 ) 3 C C 3 Na C 3 C
More informationColumbia University 92CORG14.DOC CHEM S3443D Summer 1992 Professor Grace B. Borowitz Exam No. 4 July 2, 1992
olumbia University 92RG14.D EM S3443D Summer 1992 Professor Grace B. Borowitz Exam No. 4 July 2, 1992 Name: Grade: Please use a non-red pen. Answer questions in the provided space. If you write any answers
More informationChapter 15. Reactions of Aromatic Compounds. Electrophilic Aromatic Substitution on Arenes. The first step is the slow, rate-determining step
Electrophilic Aromatic Substitution on Arenes Chapter 15 Reactions of Aromatic Compounds The characteristic reaction of aromatic rings is substitution initiated by an electrophile halogenation nitration
More informationFinal Exam Chem 3045x Wednesday, Dec. 17, 1997
Final Exam Chem 3045x Wednesday, Dec. 17, 1997 Instructions: This is a closed book examination. You may not use any notes, books or external materials during the course of the examination. Please print
More informationChapter 23 Phenols CH. 23. Nomenclature. The OH group takes precedence as the parent phenol.
CH. 23 Chapter 23 Phenols Nomenclature The OH group takes precedence as the parent phenol. Carboxyl and acyl groups take precedence over the OH group. The OH group is a strong electron-donating group through
More informationMore Nomenclature: Common Names for Selected Aromatic Groups. Aryl = Ar = aromatic group. It is a broad term, and includes any aromatic rings.
More Nomenclature: Common Names for Selected Aromatic Groups Phenyl group = or Ph = C 6 H 5 = Aryl = Ar = aromatic group. It is a broad term, and includes any aromatic rings. Benzyl = Bn = It has a -CH
More informationChemistry of Benzene: Electrophilic Aromatic Substitution
Chemistry of Benzene: Electrophilic Aromatic Substitution Why this Chapter? Continuation of coverage of aromatic compounds in preceding chapter focus shift to understanding reactions Examine relationship
More informationFacebook: UCI ORganic Chemistry Peer Tutoring King 51 Fall 2017
1 Organic Chemistry 51A Professor King Final Exam Review Session December 7 th, 2017 Will Cabanela (rcabanel@uci.edu) Amanda Pinski (apinski@uci.edu) Zachary Valley (zvalley@uci.edu) http://sites.uci.edu/ochemtutors
More information75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will
71. B SN2 stands for substitution nucleophilic bimolecular. This means that there is a bimolecular rate-determining step. Therefore, the reaction will follow second-order kinetics based on the collision
More information08. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 6 th edition, Chapter 16
08. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry, 6 th edition, Chapter 16 Benzene is a nucleophile p electrons make benzene nucleophile, like alkenes.
More informationLecture 12 (2/17/17) Phenols. Chapter 18 in Loudon, M.; Parise, J. Organic Chemistry, 6th Ed. W. H. Freeman: New York, NY, 2016
J. G. Rudick CHE 322: rganic Chemistry IIA Lecture 12 (2/17/17) Phenols Chapter 18 in Loudon, M.; Parise, J. rganic Chemistry, 6th Ed. W. H. Freeman: New York, NY, 2016 Prof. Jon Rudick ffice Hours: CHEM
More informationBENZENE AND AROMATIC COMPOUNDS
BENZENE AND AROMATIC COMPOUNDS The discovery of benzene: 1825 - Michael Faraday, empirical formula of C 1834 - Eilhard Mitscherlich synthesized benzin from gum benzoin, empirical formula C Aromatic The
More informationPLEASE DO NOT WRITE ON THE EXAM (EVEN YOUR NAME) UNTIL TOLD TO START! Student ID # CHEM 8A, Organic Chemistry EXAM 1 (300 points)
PLEASE D T WRITE TE EXAM (EVE YUR AME) UTIL TLD T START! UCSC, Binder ame Student ID # CEM 8A, rganic Chemistry EXAM (300 points) In each of the following problems, use your knowledge of organic chemistry
More informationThe now-banned diet drug fen-phen is a mixture of two synthetic substituted benzene: fenfluramine and phentermine.
The now-banned diet drug fen-phen is a mixture of two synthetic substituted benzene: fenfluramine and phentermine. Chemists have synthesized compounds with structures similar to adrenaline, producing amphetamine.
More informationOrganic Chemistry. M. R. Naimi-Jamal. Faculty of Chemistry Iran University of Science & Technology
Organic Chemistry M. R. Naimi-Jamal Faculty of Chemistry Iran University of Science & Technology Chapter 5-2. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry,
More informationSeminar_3. 1. Substituded derivatives of benzene and their nomenclature
1. Substituded derivatives of benzene and their nomenclature 2. Reactions of arenes. Electrophilic aromatic substitutions 3. Activating substituents. Orientation in the aromatic ring Seminar_3 TEST - Aromatic
More informationChem 22 Final Exam Practice
Chem 22 Final Exam Practice Questions taken from regular tests given during the previous semesters. Only one answer is correct unless the question says otherwise. The questions are somewhat scrambled with
More informationCH 24: Amines. Topics Synthesis of amines Hofmann Elimination Aryl amines Diazonium salts. Connections: CH 2 NH2. R Br R C N O NH 2 CH 3 N H 2 N + O -
rganic Chemistry otes by Jim Maxka C 24: Amines Topics Synthesis of amines ofmann Elimination Aryl amines Diazonium salts Connections: C C 2 2 2 C 2 2 2-3 - 2 2 2 C Ph- 2 Ph- Ph-C Ph- C24-1 rganic Chemistry
More information