Homework Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions mandatory problems are highlighted (up to page 16)
|
|
|
- Audra Morton
- 7 years ago
- Views:
Transcription
1 Homework Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions mandatory problems are highlighted (up to page 16) SHORT ANSWER IUPAC Naming Instructions: Provide proper IUPAC names. 1. Name: Ethyl p-aminobenzoate 2. Name: bis(2-methylpropanoic) anhydride 3. Name: methyl phenylacetate 4. Name: 1
2 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions trans-2-butenoyl chloride 5. Name: N-cyclopentyl-3-methylbutanamide Drawing Instructions: Draw structures corresponding to each of the given names. 6. Draw: 2-propenamide 7. Draw: 3,4,5-trimethoxybenzoyl chloride 8. Draw: acetic formic anhydride 2
3 Chapter Draw: N,N-dimethylformamide 10. Draw: methyl cis-3-ethylcyclobutanecarboxylate 11. Draw: (E)-2,4-dimethyl-2-hexenoyl chloride 3
4 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 12. What is the correct structure for phenylbenzoate? a. b. c. d. a Exhibit 21-1 What is the order of decreasing reactivity towards nucleophilic acyl substitution for the carboxylic acid derivatives? (most reactive first) 13. a. I, II, III, IV b. I, III, IV, II c. II, IV, III, I d. II, I, III, IV b 14. a. I, III, II, IV b. II, III, I, IV c. III, II, I, IV d. IV, I, III, II d 4
5 Chapter The ester ethyl p-nitrobenzoate is more reactive towards nucleophilic acyl substitution than ethyl p-methyoxybenzoate. Explain this reactivity difference using both words and structures. In general, any factor that makes the carbonyl carbon more polarized will increase the reactivity of the carboxylic acid derivative. In these particular examples, both are aromatic ethyl esters. It is the substituent on the aromatic ring that is affecting the reactivity difference. The electronwithdrawing nitro group increases the polarization of the carbonyl by withdrawing electrons from it through the aromatic ring. The electron donating methoxy group decreases the polarization of the carbonyl by donating electrons to it through the aromatic ring. 16. Write the complete stepwise mechanism for the basic hydrolysis of acetamide, shown below. Show all electron flow with arrows and draw all intermediate structures. 5
6 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions Exhibit 21-2 Consider the reaction below to answer the following question(s): Acid halides react with diazomethane to yield diazoketones. Excess diazomethane is used to prevent the HCl produced in the reaction from reacting with the diazoketone. 17. Refer to Exhibit Diazomethane is an example of a dipolar molecule; a molecule which is neutral overall but has charges on individual atoms. One resonance form of diazomethane is drawn below. Draw the Lewis structure of the other resonance form of diazomethane. Be sure to include all formal charges. 18. Refer to Exhibit The intermediate structures for the mechanism for the reaction of propanyl chloride with diazomethane are provide below. Show all electron flow with arrows on these structures. 6
7 Chapter 21 Exhibit 21-3 Consider the reaction below to answer the following question(s): 19. Refer to Exhibit Write the complete stepwise mechanism for this reaction. Show intermediate structures and all electron flow with arrows. 7
8 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 20. Refer to Exhibit This reaction is an example of: a. an intermolecular nucleophilic acyl substitution reaction b. an intramolecular nucleophilic acyl substitution reaction c. an intermolecular S N 2 reaction d. an intramolecular S N 2 reaction b 21. Refer to Exhibit The purpose of the base catalyst in this reaction is: a. to polarize the carbonyl group to make it more electrophilic b. to convert the ester to an intermediate carboxylic acid c. to convert the alcohol group to an alkoxide anion, which is a better nucleophile d. all of the above c 22. Refer to Exhibit The product of this reaction is: a. a lactone b. an anhydride c. a lactam d. an ether a 23. Methyl butanoate has been isolated from pineapple oil and can be prepared by the Fischer esterification reaction shown below. Write the complete stepwise mechanism for this reaction. Show all electron flow with arrows and include all intermediate structures. 8
9 Chapter Write the complete stepwise mechanism for the acid-catalyzed hydrolysis of the following amide to yield mandelic acid. Show all electron flow with arrows and draw the structures of all intermediate species. 9
10 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 25. The purpose of the acid catalyst in the hydrolysis of an amide is: a. to enhance the nucleophilicity of the water molecule b. to enhance the electrophilicity of the amide carbonyl carbon c. to enhance the electrophilicity of the water molecule d. to shift the equilibrium of the reaction b Exhibit 21-4 Consider the information below to answer the following question(s). The reaction of a carboxylic acid with an alcohol in the presence of acid is termed Fischer esterification. 26. Refer to Exhibit The nucleophile in this reaction is. B 27. Refer to Exhibit Compound C functions as in this reaction. a. a base scavenger b. a solvent c. a catalyst d. a neutralizer c 28. Refer to Exhibit Fischer esterification is an example of: a. nucleophilic acyl addition b. nucleophilic acyl substitution c. nucleophilic acyl elimination d. nucleophilic acyl rearrangement b 10
11 Chapter Refer to Exhibit Write the stepwise mechanism for the Fischer esterification reaction of benzoic acid and methanol given above. Show all electron flow by using curved arrows, and include all intermediate structures. Exhibit 21-5 Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the following reactions or sequences of reactions. Show all relevant stereochemistry
12 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
13 Chapter
14 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
15 Chapter
16 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
17 Chapter 21 Exhibit 21-6 Choose the best reagent(s) from the list provided below for carrying out the following transformations. Place the letter corresponding to the best choice in the blank to the left of the transformation. a. (Ph) 2 CuLi, ether f. 1. DIBAH, toluene b. NaBH 4, ethanol 2. H 3 O + c. 1. CH 3 MgBr, ether g. 1. (Ph) 2 CHMgBr 2. H 3 O + 2. H 3 O + d. 1. LiAlH 4, THF h PhMgBr, ether 2. H 3 O + 2. H 3 O + e. (CH 3 ) 2 CuLi, ether 45. h 46. a 47. d 17
18 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 48. f 49. d Exhibit 21-7 Show how you would accomplish each of the following transformations. More than one step may be required. Show all reagents and all intermediate structures
19 Chapter Aklomide, 2-chloro-4-nitrobenzamide, is an ingredient in veterinary antibacterial preparations. Propose a synthesis of aklomide starting with toluene. Show all reagents and all intermediate structures. 19
20 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 55. Ethyl phenylacetate is a pleasant smelling compound used in perfumery. Draw structures for each of the intermediates in the synthesis of ethyl phenylacetate below. 20
21 Chapter 21 Exhibit 21-8 For each pair of compounds below, tell which spectroscopic technique you would use to distinguish between the two members of the pair. Tell what differences you would expect to see. 56. IR 2250 cm 1 (nitrile) cm 1 (four-membered lactam) Although you would not be expected to know the absorption of a four-membered lactam, you should be able to predict that IR spectroscopy would differentiate these two compounds based solely on the nitrile absorption in the first compound and the fact that the lactam would have a carbonyl absorption somewhere in the region of cm
22 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions IR 1735 cm cm 1 (aliphatic ester) (aromatic ester) 1 H NMR methyl singlet one triplet methylene singlet one quartet 58. IR 1820, 1760 cm cm 1 (acid OH) (anhydride) cm 1 (carboxyl) 1715 cm 1 (ketone) 1 H NMR one triplet three overlapping triplets one quartet one quartet one singlet Exhibit 21-9 Refer to the data below to answer the following question(s): Kodel is a staple and filament fiber prepared from dimethyl terephthalate and 1,4- cyclohexanedimethanol. Fabric made from Kodel has good crease resistance. 59. Refer to Exhibit Draw the structure of the Kodel polymer. 22
23 Chapter Refer to Exhibit Kodel is an example of: a. a polyurethane b. a polyester c. a polyamide d. a polycarbonate b 61. Poly(ethylene terephthalate), PET, is the polymeric material of Mylar and Dacron. What are the monomers from which PET is prepared? 2. Name the following substance. Atoms other than carbon and hydrogen are labeled. 4-methylpentanoyl chloride 23
24 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 63. Name the following substance. Atoms other than carbon and hydrogen are labeled. ethyl 1-chloropropanoate MULTIPLE CHOICE 1. Which of the following will take place via nucleophilic acyl substitution? a. thioester producing and acid chloride b. ester producing a thioester c. ester producing an amide d. acid anhydride producing an acid chloride C 2. The following reaction could be classified as which type of nucleophilic acyl substitution? More than one step might be needed. a. amoniolysis b. alcoholysis. c. reduction. d. hydrolysis. e. Grignard reaction. f. c or e depending on reaction conditions. g. The reaction will not occur via nucleophilic acyl substitution. D 24
25 Chapter The following reaction could be classified as which type of nucleophilic acyl substitution? More than one step might be needed. a. amoniolysis b. alcoholysis. c. reduction. d. hydrolysis. e. Grignard reaction. f. c or e depending on reaction conditions. g. The reaction will not occur via nucleophilic acyl substitution. B 4. The following reaction could be classified as which type of nucleophilic acyl substitution? More than one step might be needed. a. amoniolysis b. alcoholysis. c. reduction. d. hydrolysis. e. Grignard reaction. f. c or e depending on the reaction conditions. g. The reaction will not occur via nucleophilic acyl substitution. C 5. The following reaction could be classified as which type of nucleophilic acyl substitution? 25
26 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions a. amoniolysis b. alcoholysis. c. reduction. d. hydrolysis. e. Grignard reaction. f. c or e depending on reaction conditions. g. The reaction will not occur via nucleophilic acyl substitution. G 6. What is the product when the following substance reacts with trimethylamine ((CH 3 ) 3 N)? Atoms other than carbon and hydrogen are labeled. a. b. c. d. D No reaction occurs. 26
27 Chapter What is the name of the product when the following substance reacts with NaCH 3 COO? Atoms other than carbon and hydrogen are labeled. a. 4-methylbutanoic acid b. acetic 4-methylbutanoic anhydride c. 4-methylbutyl acetate d. acetyl 4-methylbutanoate e. No reaction occurs. B 8. Which line in the following spectrum would indicate the presence of a carbonyl group? a. 1 b. 2 c. 3 d. 4 e. 5 E 27
28 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 9. Based on the following spectrum the sample used would probably be classified as a(n): a. aldehyde. b. ketone. c. ester. d. The spectrum is not specific enough to classify the substance. C 10. The following is an excerpt from a spectrum taken on an unknown sample. To which of the following functional groups might the unknown belong? a. amide b. acid chloride c. carboxylic acid d. ester e. None of these can be eliminated. D 28
29 Chapter Consider the following molecular model. Atoms other than carbon and hydrogen are labeled. Which of the following reactants could be used to produce this compound? a. 1-chloropropanoic acid and ethanol b. propanoic acid and chloroethanol c. propanoic acid and ethanol A 12. Consider the structure given below which might be found in a protein. Which of the following is not applicable to this structure? a. contains three monomers b. contains amide bonds c. formed from a diacid and diamine d. contains three types of monomers e. All of these apply to this structure. C 13. Which of the following describes nucleophilic acyl substitution? a. Nucleophile adds to the electrophilic carbon of the carbonyl bond. b. Electrophile replaces a group on the carbon alpha to the carbonyl. c. Nucleophile replaces a group adjacent to the carbon of carbonyl. d. Two carbonyl groups react with each other. C 29
Ch17_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
Ch17_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Which molecule is a carboxylic acid? A) 1) B) C) D) E) CH3 CH2 CH2 NH2 2) Which molecule
Carboxylic Acid Derivatives and Nitriles
Carboxylic Acid Derivatives and itriles Carboxylic Acid Derivatives: There are really only four things to worry about under this heading; acid chlorides, anhydrides, esters and amides. We ll start with
HOMEWORK PROBLEMS: IR SPECTROSCOPY AND 13C NMR. The peak at 1720 indicates a C=O bond (carbonyl). One possibility is acetone:
HMEWRK PRBLEMS: IR SPECTRSCPY AND 13C NMR 1. You find a bottle on the shelf only labeled C 3 H 6. You take an IR spectrum of the compound and find major peaks at 2950, 1720, and 1400 cm -1. Draw a molecule
1. The functional group present in carboxylic acids is called a A) carbonyl group. B) carboxyl group. C) carboxylate group. D) carbohydroxyl group.
Name: Date: 1. The functional group present in carboxylic acids is called a A) carbonyl group. B) carboxyl group. C) carboxylate group. D) carbohydroxyl group. 2. Which of the following statements concerning
Writing a Correct Mechanism
Chapter 2 1) Balancing Equations Writing a Correct Mechanism 2) Using Arrows to show Electron Movement 3) Mechanisms in Acidic and Basic Media 4) Electron rich Species: Nucleophile or Base? 5) Trimolecular
21.9 REDUCTION OF CARBOXYLIC ACID DERIVATIVES
10 APTER 1 TE EMITRY F ARBXYLI AID DERIVATIVE TUDY GUIDE LIK 1.5 Esters and ucleophiles 1.17 Give the structure of the product in the reaction of each of the following esters with isotopically labeled
4/18/2011. 9.8 Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions
9.8 Substituent effects in the electrophilic substitution of an aromatic ring Substituents affect the reactivity of the aromatic ring Some substituents activate the ring, making it more reactive than benzene
Determining the Structure of an Organic Compound
Determining the Structure of an Organic Compound The analysis of the outcome of a reaction requires that we know the full structure of the products as well as the reactants In the 19 th and early 20 th
UNIT (9) CARBOXYLIC ACIDS, ESTERS, AMINES, AND AMIDES
UNIT (9) CARBXYLIC ACIDS, ESTERS, AMINES, AND AMIDES 9.1 Carboxylic Acids The functional group in carboxylic acids is called the carboxyl group. A carboxyl group is a carbonyl group (C = ) with a hydroxyl
Unit Vocabulary: o Organic Acid o Alcohol. o Ester o Ether. o Amine o Aldehyde
Unit Vocabulary: Addition rxn Esterification Polymer Alcohol Ether Polymerization Aldehyde Fermentation Primary Alkane Functional group Saponification Alkene Halide (halocarbon) Saturated hydrocarbon Alkyne
CHEM 211 CHAPTER 16 - Homework
CHEM 211 CHAPTER 16 - Homework SHORT ANSWER Consider the Friedel-Crafts alkylation reaction below to answer the following question(s): 1. Refer to the reaction above. Draw the structure of the electrophilic
Page 1. 6. Which hydrocarbon is a member of the alkane series? (1) 1. Which is the structural formula of methane? (1) (2) (2) (3) (3) (4) (4)
1. Which is the structural formula of methane? 6. Which hydrocarbon is a member of the alkane series? 7. How many carbon atoms are contained in an ethyl group? 1 3 2 4 2. In the alkane series, each molecule
But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).
Reactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. Normally: Oxidation
Chemistry Notes for class 12 Chapter 13 Amines
1 P a g e Chemistry Notes for class 12 Chapter 13 Amines Amines constitute an important class of organic compounds derived by replacing one or more hydrogen atoms ofnh 3 molecule by alkyl/aryl group(s).
Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations SHORT ANSWER Exhibit 11-1 Circle your response in each set below. 1. Circle the least
for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency of the vibration
! = 1 2"c k (m + M) m M wavenumbers! =!/c = 1/" wavelength frequency! units: cm 1 for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency
Name. Department of Chemistry and Biochemistry SUNY/Oneonta. Chem 322 - Organic Chemistry II Examination #2 - March 14, 2005 ANSWERS
Name INSTRUTINS --- Department of hemistry and Biochemistry SUNY/neonta hem 322 - rganic hemistry II Examination #2 - March 14, 2005 ANSWERS This examination has two parts. Part I is in multiple choice
Unit 2 Review: Answers: Review for Organic Chemistry Unit Test
Unit 2 Review: Answers: Review for Organic Chemistry Unit Test 2. Write the IUPAC names for the following organic molecules: a) acetone: propanone d) acetylene: ethyne b) acetic acid: ethanoic acid e)
Organic Chemistry, 5e (Bruice) Chapter 17: Carbonyl Compounds II
Organic Chemistry, 5e (Bruice) Chapter 17: Carbonyl Compounds II 1) Which of the following compounds is an aldehyde? A) I B) II C) III D) IV E) V D Section: 17-1 2) Which of the following compounds is
CH 102 Practice Exam 2 PCC-Sylvania
CH 102 Practice Exam 2 PCC-Sylvania True/False Indicate if the statement is true or false. 1.Tertiary alcohols are not easily oxidized. 2.Secondary alcohols can be oxidized to aldehydes. 3.Primary alcohols
Chapter 22 Carbonyl Alpha-Substitution Reactions
John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 22 Carbonyl Alpha-Substitution Reactions The α Position The carbon next to the carbonyl group is designated as being in the α position Electrophilic
Chapter 13 Carboxylic Acids, Esters, Amines, and Amides. Carboxylic Acids. Names and Sources of Some Carboxylic Acids. IUPAC Names
Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.1 Carboxylic Acids Carboxylic Acids A carboxylic acid contains a carboxyl group, which is a carbonyl group (C=) attached to a hydroxyl group (
Synthesis of Isopentyl Acetate
Experiment 8 Synthesis of Isopentyl Acetate Objectives To prepare isopentyl acetate from isopentyl alcohol and acetic acid by the Fischer esterification reaction. Introduction Esters are derivatives of
Assessment Schedule 2013 Chemistry: Demonstrate understanding of the properties of organic compounds (91391)
NCEA Level 3 Chemistry (91391) 2013 page 1 of 8 Assessment Schedule 2013 Chemistry: Demonstrate understanding of the properties of organic compounds (91391) Evidence Statement Q Evidence Achievement Achievement
MOLECULAR REPRESENTATIONS AND INFRARED SPECTROSCOPY
MLEULAR REPRESENTATINS AND INFRARED SPETRSPY A STUDENT SULD BE ABLE T: 1. Given a Lewis (dash or dot), condensed, bond-line, or wedge formula of a compound draw the other representations. 2. Give examples
Experiment 11. Infrared Spectroscopy
Chem 22 Spring 2010 Experiment 11 Infrared Spectroscopy Pre-lab preparation. (1) In Ch 5 and 12 of the text you will find examples of the most common functional groups in organic molecules. In your notebook,
Please read and sign the Honor Code statement below:
CHEM 3311 Exam #1 Name Dr. Minger June 8, 2015 Please read and sign the Honor Code statement below: I pledge that on my honor, as a University of Colorado at Boulder student, I have neither given nor received
Electrophilic Aromatic Substitution Reactions
Electrophilic Aromatic Substitution Reactions, Course Notes Archive, 1 Electrophilic Aromatic Substitution Reactions An organic reaction in which an electrophile substitutes a hydrogen atom in an aromatic
For example: (Example is from page 50 of the Thinkbook)
SOLVING COMBINED SPECTROSCOPY PROBLEMS: Lecture Supplement: page 50-53 in Thinkbook CFQ s and PP s: page 216 241 in Thinkbook Introduction: The structure of an unknown molecule can be determined using
Organic Functional Groups Chapter 7. Alcohols, Ethers and More
Organic Functional Groups Chapter 7 Alcohols, Ethers and More 1 What do you do when you are in Pain? What do you do when you are in a lot of pain? 2 Functional Groups A functional group is an atom, groups
Electrophilic Aromatic Substitution
Electrophilic Aromatic Substitution Electrophilic substitution is the typical reaction type for aromatic rings. Generalized electrophilic aromatic substitution: E E Electrophile Lewis acid: may be or neutral.
Copyright 2010 Pearson Education, Inc. Chapter Fourteen 1
An alcohol has an OH bonded to an alkyl group; a phenol has an OH bonded directly to an aromatic ring; and an ether has an O bonded to two organic groups. Chapter Fourteen 1 Ethyl alcohol, dimethyl ether,
Amides and Amines: Organic Nitrogen Compounds
Chapter 25 Amides and Amines: Organic Nitrogen Compounds Nylon is one of the materials used to give these colorful sails their strength and durability. Introduction to General, Organic, and Biochemistry,
Aldehydes can react with alcohols to form hemiacetals. 340 14. Nucleophilic substitution at C=O with loss of carbonyl oxygen
340 14. Nucleophilic substitution at C= with loss of carbonyl oxygen Ph In Chapter 13 we saw this way of making a reaction go faster by raising the energy of the starting material. We also saw that the
These instructions are for a classroom activity which supports OCR A Level Chemistry A.
Lesson Element Keyword activities Instructions for teachers These instructions are for a classroom activity which supports OCR A Level Chemistry A. Just a minute! To run this activity you will need a set
Chapter 12 Organic Compounds with Oxygen and Sulfur
Chapter 12 Organic Compounds with Oxygen and Sulfur 1 Alcohols An alcohol contains a hydroxyl group ( OH) that replaces a hydrogen atom in a hydrocarbon. A phenol contains a hydroxyl group ( OH) attached
Chapter 5 Classification of Organic Compounds by Solubility
Chapter 5 Classification of Organic Compounds by Solubility Deductions based upon interpretation of simple solubility tests can be extremely useful in organic structure determination. Both solubility and
Introduction to Biodiesel Chemistry Terms and Background Information
Introduction to Biodiesel Chemistry Terms and Background Information Basic rganic Chemistry rganic chemistry is the branch of chemistry that deals with organic compounds. rganic compounds are compounds
Alcohols An alcohol contains a hydroxyl group ( OH) attached to a carbon chain. A phenol contains a hydroxyl group ( OH) attached to a benzene ring.
Chapter : rganic Compounds with xygen Alcohols, Ethers Alcohols An alcohol contains a hydroxyl group ( H) attached to a carbon chain. A phenol contains a hydroxyl group ( H) attached to a benzene ring.
Organic Chemistry Tenth Edition
Organic Chemistry Tenth Edition T. W. Graham Solomons Craig B. Fryhle Welcome to CHM 22 Organic Chemisty II Chapters 2 (IR), 9, 3-20. Chapter 2 and Chapter 9 Spectroscopy (interaction of molecule with
A Grignard reagent formed would deprotonate H of the ethyl alcohol OH.
216 S11-E2 Page 2 Name Key I. (9 points) Answer in the boxes below the following questions for the Grignard reagent C 3 -Mg. (1) (2 points) Is the carbon atom associated with magnesium electrophilic or
Infrared Spectroscopy
Infrared Spectroscopy 1 Chap 12 Reactions will often give a mixture of products: OH H 2 SO 4 + Major Minor How would the chemist determine which product was formed? Both are cyclopentenes; they are isomers.
Carbonyl Chemistry (12 Lectures)
arbonyl hemistry (12 Lectures) Aim of ourse Professor Donna G. Blackmond d.blackmond@imperial.ac.uk tel. 41193 oom 639 1 To build upon elements of Dr E.. Smith s and Dr. D.. Braddocks s course. To introduce
Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil
Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil Textbook and Materials What you must buy: Organic Chemistry 4 th Ed. Janice G. Smith, McGraw Hill. (Older edition is fine) Chem
Q.1 Draw out some suitable structures which fit the molecular formula C 6 H 6
Aromatic compounds GE 1 BENZENE Structure Primary analysis revealed benzene had an... empirical formula of and a molecular formula of 6 6 Q.1 Draw out some suitable structures which fit the molecular formula
CHEM 121. Chapter 17. Name: Date:
CHEM 121. Chapter 17. Name: Date: 1. The elements present in a tertiary amine with two phenyl groups are A) carbon and nitrogen B) carbon, nitrogen and hydrogen C) carbon, nitrogen and oxygen D) carbon,
Carboxylic Acid Structure and Chemistry: Part 2
Principles of Drug Action 1, pring 2005, Carboxylic Acids Part 2 Carboxylic Acid tructure and Chemistry: Part 2 Jack Deuiter IV. eactions of the Carboxylic Acid eactions Depending on their overall structure,
CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway. CHAPTER 14 Substitution Reactions of Aromatic Compounds
CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway "Organic Chemistry" by Maitland Jones, 4 th edition Chapter 14 Homework: 1, 2, 5, 7, 13, 19, 20, 23, 26, 27, 28, 30, 31, 34, 35, 36, 41, 46,
Name of mechanism...... (1) For Step 3, give the reagent, give a necessary condition and name the mechanism. Reagent... Condition...
Q. A possible synthesis of the amino acid X is shown below. (a) Name and outline a mechanism for Step. Name of mechanism... Mechanism (5) (b) Give the IUPAC name of the product of Step.... () (c) For Step,
ammonium salt (acidic)
Chem 360 Jasperse Ch. 19 otes. Amines 1 eactions of Amines 1. eaction as a proton base (Section 19-5 and 19-6) amine base -X (proton acid) a X ammonium salt (acidic) Mechanism: equired (protonation) everse
How to Quickly Solve Spectrometry Problems
How to Quickly Solve Spectrometry Problems You should be looking for: Mass Spectrometry (MS) Chemical Formula DBE Infrared Spectroscopy (IR) Important Functional Groups o Alcohol O-H o Carboxylic Acid
Typical Infrared Absorption Frequencies. Functional Class Range (nm) Intensity Assignment Range (nm) Intensity Assignment
Typical Infrared Absorption Frequencies Functional Class Range (nm) Intensity Assignment Range (nm) Intensity Assignment Alkanes 2850-3000 CH 3, CH 2 & CH 2 or 3 bands Alkenes 3020-3100 1630-1680 1900-2000
IDENTIFICATION OF ALCOHOLS
IDENTIFICATION OF ALCOHOLS Alcohols are organic compounds that which considered as derivatives of water. One of the hydrogen atoms of water molecule (H-O-H) has been replaced by an alkyl or substituted
Avg. 16.4 / 25 Stnd. Dev. 8.2
QUIZ TREE Avg. 16.4 / 25 Stnd. Dev. 8.2 xidation of Alcohols with Chromium (VI): Jones xidation 2 Alcohols are oxidized by a solution of chromium trioxide in aqueous acetone (2), in the presence of an
Identification of Unknown Organic Compounds
Identification of Unknown Organic Compounds Introduction The identification and characterization of the structures of unknown substances are an important part of organic chemistry. Although it is often
DETERMINACIÓN DE ESTRUCTURAS ORGÁNICAS (ORGANIC SPECTROSCOPY) IR SPECTROSCOPY
DETERMINACIÓN DE ESTRUCTURAS ORGÁNICAS (ORGANIC SPECTROSCOPY) IR SPECTROSCOPY Hermenegildo García Gómez Departamento de Química Instituto de Tecnología Química Universidad Politécnica de Valencia 46022
Chapter 2 Polar Covalent Bonds; Acids and Bases
John E. McMurry http://www.cengage.com/chemistry/mcmurry Chapter 2 Polar Covalent Bonds; Acids and Bases Javier E. Horta, M.D., Ph.D. University of Massachusetts Lowell Polar Covalent Bonds: Electronegativity
passing through (Y-axis). The peaks are those shown at frequencies when less than
Infrared Spectroscopy used to analyze the presence of functional groups (bond types) in organic molecules The process for this analysis is two-fold: 1. Accurate analysis of infrared spectra to determine
INTDUCTIN T LEWIS ACID-BASE CEMISTY DEINITINS Lewis acids and bases are defined in terms of electron pair transfers. A Lewis base is an electron pair donor, and a Lewis acid is an electron pair acceptor.
Chapter 6 An Overview of Organic Reactions
John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 6 An Overview of Organic Reactions Why this chapter? To understand organic and/or biochemistry, it is necessary to know: -What occurs -Why and
The Four Questions to Ask While Interpreting Spectra. 1. How many different environments are there?
1 H NMR Spectroscopy (#1c) The technique of 1 H NMR spectroscopy is central to organic chemistry and other fields involving analysis of organic chemicals, such as forensics and environmental science. It
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
Ch14_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Compounds with the -OH group attached to a saturated alkane-like carbon are known as A)
NOMENCLATURE OF ORGANIC COMPOUNDS 2010, 2003, 1980, by David A. Katz. All rights reserved.
NMENCLATURE F RGANIC CMPUNDS 2010, 2003, 1980, by David A. Katz. All rights reserved. rganic chemistry is the chemistry of carbon compounds. Carbon has the ability to bond with itself to form long chains
2. Couple the two protected amino acids.
General Considerations The Strategy of Peptide Synthesis Making peptide bonds between amino acids is not difficult. The challenge is connecting amino acids in the correct sequence. andom peptide bond formation
CHEM 51LB EXP 1 SPECTROSCOPIC METHODS: INFRARED AND NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
CHEM 51LB EXP 1 SPECTRSCPIC METHDS: INFRARED AND NUCLEAR MAGNETIC RESNANCE SPECTRSCPY REACTINS: None TECHNIQUES: IR Spectroscopy, NMR Spectroscopy Infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy
Alcohols. Characterized by OH group Name: add ol. to name of hydrocarbon. Methanol. Butanol. Sterno. Alcohols burn in air. A mixture of ethanol +
1 2 3 Functional Groups Alcohols Structures of Alcohols haracterized by group Name: add ol to name of hydrocarbon 3 5 : how many structural isomers? See D-RM Screens 11.5 & 11.6 Methanol Butanol 1-propanol
Q.1 Draw structures for, and name, all carboxylic acids with formula :-
arboxylic acids F4 1 ARBXYLI AIDS Structure contain the carboxyl functional group includes a carbonyl (=) group and a hydroxyl (-) group the bonds are in a planar arrangement are isomeric with esters :-
methyl RX example primary RX example secondary RX example secondary RX example tertiary RX example
ucleophilic Substitution & Elimination hemistry 1 eginning patterns to knowfor S and E eactions - horizontal and vertical templates for practice Example 1 - two possible perspectives (deuterium and tritium
The dipolar nature of acids
I. Introduction arboxylic Acid Structure and hemistry: Part 1 Jack Deuiter arboxylic acids are hydrocarbon derivatives containing a carboxyl () moiety. ecall that carbon has four valence electrons and
Chapter 2 - Polar Covalent Bonds; Acids and Bases
Chapter 2 - Polar Covalent Bonds; Acids and Bases For questions 1-10 give the letter of the term that best matches the given definition. a. Brønsted-Lowry Acid f. Ionic Bond b. Brønsted-Lowry Base g. Covalent
Boston University Dresden Science Program ORGANIC CHEMISTRY CAS CH 203 Lecture
Boston University Dresden Science Program ORGANIC CHEMISTRY CAS CH 203 Lecture Instructor: Professor Wolf D. Habicher, Professor Claus Rüger Meeting Times Lectures: twice a week at 90 minutes each Discussions:
2. Rank the following three compounds in decreasing order of basicity. O NHCCH 3 NH 2
1. To convert a nitrile to a primary amine you must: A) hydrolyze it with water. B) oxidize it with chromic acid. C) reduce it with hydrogen or lithium aluminum hydride. D) substitute it with an alkyl
INTERMOLECULAR FORCES
INTERMOLECULAR FORCES Intermolecular forces- forces of attraction and repulsion between molecules that hold molecules, ions, and atoms together. Intramolecular - forces of chemical bonds within a molecule
CHEM 208(Organic Chemistry I) Instructor: Dr. Niranjan Goswami. Tel: (618)545-3361. Email: Ngoswami@kaskaskia.edu. Web: www.kc.cc.il.
CHEM 208(Organic Chemistry I) Instructor: Dr. Niranjan Goswami Tel: (618)545-3361 Email: Ngoswami@kaskaskia.edu Web: www.kc.cc.il.us/ngoswami CHEM 208 COURSE SYLLABUS KASKASKIA COLLEGE NAME TERM YEAR TEXT:
ALCOHOLS: Properties & Preparation
ALLS: Properties & Preparation General formula: R-, where R is alkyl or substitued alkyl. Ar-: phenol - different properties. Nomenclature 1. ommon names: Name of alkyl group, followed by word alcohol.
Nucleophilic Substitution and Elimination
Nucleophilic Substitution and Elimination What does the term "nucleophilic substitution" imply? A nucleophile is an the electron rich species that will react with an electron poor species A substitution
Infrared Spectroscopy 紅 外 線 光 譜 儀
Infrared Spectroscopy 紅 外 線 光 譜 儀 Introduction Spectroscopy is an analytical technique which helps determine structure. It destroys little or no sample (nondestructive method). The amount of light absorbed
pk a Values for Selected Compounds
Appendix A pk a Values for Selected ompounds ompound pk a ompound pk a I 10 Br 9 2 S 4 9 + 3 3 7.3 3 S 3 7 Br 4.0 4.2 3 4.3 2 N l 7 [( 3 ) 2 ] + 3.8 [ 3 2 ] + 2.5 3 + 1.7 3 S 3 1.2 + 3 N2 0.0 F 3 0.2 l
Laboratory 22: Properties of Alcohols
Introduction Alcohols represent and important class of organic molecules. In this experiment you will study the physical and chemical properties of alcohols. Solubility in water, and organic solvents,
CH243: Lab 4 Synthesis of Artificial Flavorings by Fischer Esterification
H243: Lab 4 Synthesis of Artificial Flavorings by Fischer Esterification PURPSE: To prepare esters by reaction of carboxylic acids and alcohols. To modify a known procedure to prepare an unknown. DISUSSIN:
Benzene Benzene is best represented as a resonance hybrid:
Electrophilic Aromatic Substitution (EAS) is a substitution reaction usually involving the benzene ring; more specifically it is a reaction in which the hydrogen atom of an aromatic ring is replaced as
Symmetric Stretch: allows molecule to move through space
BACKGROUND INFORMATION Infrared Spectroscopy Before introducing the subject of IR spectroscopy, we must first review some aspects of the electromagnetic spectrum. The electromagnetic spectrum is composed
Mass Spec - Fragmentation
Mass Spec - Fragmentation An extremely useful result of EI ionization in particular is a phenomenon known as fragmentation. The radical cation that is produced when an electron is knocked out of a neutral
Reactions of Fats and Fatty Acids
Reactions of Fats and Fatty Acids Outline Fats and Oils Fatty Acid Biosynthesis Biodiesel Homework We hear quite a lot about the place of fats and oils in human nutrition. Foods high in fat are at the
Sample exam questions for First exam CHM 2211
Sample exam questions for First exam CM 2211 1. The IR absorption due to the stretching of which of these carbon-hydrogen bonds occurs at the highest frequency? I II III E) V IV V 2. ow many signals would
Lecture Overview. Hydrogen Bonds. Special Properties of Water Molecules. Universal Solvent. ph Scale Illustrated. special properties of water
Lecture Overview special properties of water > water as a solvent > ph molecules of the cell > properties of carbon > carbohydrates > lipids > proteins > nucleic acids Hydrogen Bonds polarity of water
Topics to be Covered. Elements of Step-Growth Polymerization. Branching Network Formation
Topics to be Covered Elements of Step-Growth Polymerization Branching Network Formation Chapters 1 & 2 in CD (Polymer Science and Engineering) Dawn of Understanding "I am inclined to think that the development
Solving Spectroscopy Problems
Solving Spectroscopy Problems The following is a detailed summary on how to solve spectroscopy problems, key terms are highlighted in bold and the definitions are from the illustrated glossary on Dr. Hardinger
The Aldol Condensation
The Aldol ondensation Synthesis and Analysis of 2,3,4,5-Tetraphenylcyclopentadienone Yakety Sax Bennie ill theme song TPP eactions of Aldehydes and Ketones ' 1. Nucleophilic Addition. 2. Substitution at
Chapter 2 Polar Covalent Bonds: Acids and Bases
John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 2 Polar Covalent Bonds: Acids and Bases Modified by Dr. Daniela R. Radu Why This Chapter? Description of basic ways chemists account for chemical
NMR Spectroscopy of Aromatic Compounds (#1e)
NMR Spectroscopy of Aromatic Compounds (#1e) 1 H NMR Spectroscopy of Aromatic Compounds Erich Hückel s study of aromaticity in the 1930s produced a set of rules for determining whether a compound is aromatic.
Suggested solutions for Chapter 3
s for Chapter PRBLEM Assuming that the molecular ion is the base peak (00% abundance) what peaks would appear in the mass spectrum of each of these molecules: (a) C5Br (b) C60 (c) C64Br In cases (a) and
How to Interpret an IR Spectrum
How to Interpret an IR Spectrum Don t be overwhelmed when you first view IR spectra or this document. We have simplified the interpretation by having you only focus on 4/5 regions of the spectrum. Do not
Chapter 11 Structure Determination: Nuclear Magnetic Resonance Spectroscopy. Nuclear Magnetic Resonance Spectroscopy. 11.1 Nuclear Magnetic Resonance
John E. McMurry http://www.cengage.com/chemistry/mcmurry Chapter 11 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 11.1 Nuclear Magnetic Resonance Spectroscopy Many atomic nuclei behave
Properties of Alcohols and Phenols Experiment #3
Properties of Alcohols and Phenols Experiment #3 Objectives: To observe the solubility of alcohols relative to their chemical structure, to perform chemical tests to distinguish primary, secondary and
The chemical interactions of the template molecule are primarily dependent on the choice of polymer
Study of the Surface Morphology of Methyl 4-nitrobenzoate Template Thin-film Molecularly Imprinted Polymers Gary Kaganas Dartmouth College and Center for Nanomaterials Research at Dartmouth, Hanover NH
ACID and BASES - a Summary
AID and BASES - a Summary Stefan Svensson 2004 Brönsted-Lowry : Acids donate protons Lewis -acid : Electron pair acceptor Bases accept protons Lewis-base: Electron pair donator. Acetic acid ättiksyra 3
Acids and Bases. but we will use the term Lewis acid to denote only those acids to which a bond can be made without breaking another bond
Acids and Bases. Brønsted acids are proton donors, and Brønsted bases are proton acceptors. Examples of Brønsted acids: HCl, HBr, H 2 SO 4, HOH, H 3 O +, + NH 4, NH 3, CH 3 CO 2 H, H CH 2 COCH 3, H C CH,
Name Lab #3: Solubility of Organic Compounds Objectives: Introduction: soluble insoluble partially soluble miscible immiscible
Lab #3: Solubility of rganic Compounds bjectives: - Understanding the relative solubility of organic compounds in various solvents. - Exploration of the effect of polar groups on a nonpolar hydrocarbon
Study of the Thermal Behavior of Azidohetarenes with Differential Scanning Calorimetry
Fourth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-4), www.mdpi.org/ecsoc-4.htm, September 1-30, 2000 [A0066] Study of the Thermal Behavior of Azidohetarenes with Differential