Chapter 10 Problems , 42-43,

Size: px
Start display at page:

Download "Chapter 10 Problems , 42-43,"

Transcription

1 Chapter 10 Problems , 42-43, Synthetic Uses of Substitution and Elimination Reactions This chapter discusses how one can use substitution and elimination reactions to synthesize organic molecules Substitution Reactions Reactions that proceed via the S N 2 mechanism are preferred. Changes in stereochemistry and rearrangements are observed for S N 1 reactions. Substrates with leaving groups attached to 1 o and methyl carbons are excellent S N 2 reactants, 2 o carbons are ok as long as the nucleophile is weakly basic. S N 1 reactions must be used for substrates with leaving groups attached to 3 o carbons Preparation of Alcohols Alcohols can be prepared for alkyl halides using either HO - or H 2 O as a nucleophile. Hydroxide ion reacts with 1 o alkyl halides or 2 o halides that are either benzylic, allylic, or adjacent to a carbonyl. Examples Hydroxide is not typically used for 3 o alkyl halides due to the competing E2 reaction. Water is used as the nucleophile and reactions follow an S N 1 mechanism. Example The reaction of 2 o alkyl halides with hydroxide gives poor yield of substitution products to the competing E2 reaction. So one can use a less basic hydroxide alternative acetate (CH 3 CO 2 - ). Acetate gives better yield of substitution product and then subsequent reaction with hydroxide yields the desired alcohol. Example

2 10.3 Preparation of Ethers Ethers can be formed by using alcohols or alkoxide as the nucleophile. When alkoxide is used as the nucleophile the reaction is termed the Williamson Ether Synthesis. Example Unsymmetrical ethers can be prepared via two different Williamson ether syntheses. Since alkoxides are strong bases one would prefer to use 1 o or Methyl alkyl halides when possible. Ethers can also be prepared by using alcohols as the nucleophile when the leaving group is attached to a secondary or tertiary carbon. Cyclic ethers are readily formed if the resulting ring is 3, 5, or 6 membered.

3 10.4 Preparation of Esters Esters can be prepared by using carboxylate salts as nucleophiles. Elimination is not a problem due to the low basicity of carboxylates. Ex Preparation of Alkyl Halides Alkyl halides are frequently prepared from alcohols. Since HO - is a poor leaving group the OH group must be converted into a better leaving group, -OH 2 +, -OTs, or OMs, Or via reaction with SOCl 2, PBr 3, or PCl 3. Or displacement by another halide Preparation of Amines Ammonia and unhindered amines are good nucleohpiles. Reaction of 2 o or 3 o amines with alkyl halides provides a good yield of 3 o amines or quaternary ammonium salts. 1 o amines and ammonia have significant problems with multiple alkylations.

4 The Gabriel synthesis of 1 o amines was developed to overcome this problem. The Gabriel synthesis uses Phthalimide as an ammonium equivalent Preparation of Hydrocarbons Hydrocarbons can prepared by replacing a leaving group with a hydrogen. Lithium aluminum hydride (LiAlH 4 ) and sodium borohydride (NaBH 4 ) react as nucleophilic hydride ion. These compounds are also basic and have problems when the leaving group is on a 3 o carbon Formation of Carbon-Carbon Bonds The formation of C-C bonds is one of the more difficult tasks in organic chemistry. This usually requires the use of a carbon nucleophile carbanion. The first case is the cyanide ion ( - CN) which is a weak base but good nucleophile. Yields are good for Me, 1 o and 2 o substrates. Example A second important type of carbon nucleophile are acetylide anions R-C C: -. These anions are generated by reaction of terminal alkynes with a strong base. EX: Acetylide anions are both good nucelophiles and strong bases. Thus S N 2 reactions are favorable with Me and 1 o substrates but 2 o and 3 o give mainly elimination products. EX:

5 10.9 Phosphorus and Sulfur Nucleophiles Sulfur compounds are weaker bases but stronger nucleophiles than the corresponding oxygen compounds. Elimination reactions are not usually a problem for Me, 1 o, or 2 o substrates. EX Phosphorus nucleophiles, most frequently triphenylphosphine, are also useful Ring Opening of Epoxides While most ethers are unlikely to undergo substitution reactions, the ring strain in epoxides allows one of the C-O bonds to be broken in a substitution reaction. These reactions can be done either under acidic or basic conditions. Under basic conditions the reaction follows and S N 2 mechanism which inverts the stereocenter and the substitution occurs at the less hindered site. Ex When the reaction is conducted under acidic conditions the reaction follows a mechanism between S N 1 and the S N 2. The substitution occurs at the more stable more substituted carbon, but still occurs with retention. Ex Elimination of Hydrogen Halide (Dehydrohalogenation) Elimination reactions provide good yields of alkenes, as long as the reactions are conducted under conditions which limit the competing substitution products. However, one also encounters problems with the regio-control of the reactions (Zaitsev, Hofmann, cis/trans) Ex Preparation of Alkynes Alkynes can be prepared from dihaloalkanes by elimination of twp equivalents of HX. This reaction usually requires a strong base (KOH at high T or NaNH 2 ). Ex

6 10.13 Dehydration While one can use HX to convert alcohols to alkyl halides, the use of sulfruric or phosphoric acid results in elimination (termed dehydration). Ex Eliminations to form Carbon-Oxygen Bonds; Oxidation Reactions In organic chemistry oxidation is a reaction that results in an increase in the oxygen content or decrease in the hydrogen content of a compound, reduction is a reaction that decreases the oxygen content or increases the hydrogen content. Ex.

But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).

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

More information

Carboxylic Acid Derivatives and Nitriles

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

More information

Chapter 22 Carbonyl Alpha-Substitution Reactions

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

More information

methyl RX example primary RX example secondary RX example secondary RX example tertiary RX example

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

More information

ALCOHOLS: Properties & Preparation

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.

More information

21.9 REDUCTION OF CARBOXYLIC ACID DERIVATIVES

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

More information

Assessment Schedule 2013 Chemistry: Demonstrate understanding of the properties of organic compounds (91391)

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

More information

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 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

More information

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

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)

More information

CH 102 Practice Exam 2 PCC-Sylvania

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

More information

Acids and Bases: Molecular Structure and Acidity

Acids and Bases: Molecular Structure and Acidity Acids and Bases: Molecular Structure and Acidity Review the Acids and Bases Vocabulary List as needed. Tutorial Contents A. Introduction B. Resonance C. Atomic Radius D. Electronegativity E. Inductive

More information

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. 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

More information

Chemistry Notes for class 12 Chapter 13 Amines

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).

More information

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.

More information

IDENTIFICATION OF ALCOHOLS

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

More information

23.7 ALKYLATION AND ACYLATION REACTIONS OF AMINES

23.7 ALKYLATION AND ACYLATION REACTIONS OF AMINES 3.7 ALKYLATIN AND ACYLATIN REACTIN F AMINE 1131 organic phase organic phase organic phase CH 3 (CH ) 6 CH Br CH 3 (CH ) 6 CH Br CH 3 (CH ) 6 CH CN R 4 P Br R 4 P CN R 4 P Br Na CN Na Br Na Br aqueous phase

More information

Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil

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

More information

Writing a Correct Mechanism

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

More information

Name. Department of Chemistry and Biochemistry SUNY/Oneonta. Chem 322 - Organic Chemistry II Examination #2 - March 14, 2005 ANSWERS

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

More information

Chemical Reactions in Water Ron Robertson

Chemical Reactions in Water Ron Robertson Chemical Reactions in Water Ron Robertson r2 f:\files\courses\1110-20\2010 possible slides for web\waterchemtrans.doc Properties of Compounds in Water Electrolytes and nonelectrolytes Water soluble compounds

More information

Mass Spec - Fragmentation

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

More information

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. 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,

More information

Unit Vocabulary: o Organic Acid o Alcohol. o Ester o Ether. o Amine o Aldehyde

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

More information

Nucleophilic Substitution and Elimination

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

More information

Electrophilic Aromatic Substitution Reactions

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

More information

for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency of the vibration

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

More information

Chapter 2 Polar Covalent Bonds; Acids and Bases

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

More information

3.4 BRØNSTED LOWRY ACIDS AND BASES

3.4 BRØNSTED LOWRY ACIDS AND BASES 96 CAPTER 3 ACIDS AND BASES. TE CURVED-ARROW NOTATION and that the unshared electron pair (and negative charge) is shared equally by the two terminal carbons. C L C A C 1 allyl anion (c) Using the curved-arrow

More information

Carboxylic Acid Structure and Chemistry: Part 2

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,

More information

Chapter 12 Organic Compounds with Oxygen and Sulfur

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

More information

4/18/2011. 9.8 Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions

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

More information

ammonium salt (acidic)

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

More information

Chapter 15 Radical Reactions. Radicals are reactive species with a single unpaired electron, formed by

Chapter 15 Radical Reactions. Radicals are reactive species with a single unpaired electron, formed by Chapter 15 Radical Reactions Radicals are reactive species with a single unpaired electron, formed by homolysis of a covalent bond; a radical contains an atom that does not have an octet of electrons,

More information

HOMEWORK PROBLEMS: IR SPECTROSCOPY AND 13C NMR. The peak at 1720 indicates a C=O bond (carbonyl). One possibility is acetone:

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

More information

How to Interpret an IR Spectrum

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

More information

CHEM 121. Chapter 17. Name: Date:

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,

More information

Chapter 5 Classification of Organic Compounds by Solubility

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

More information

UNIT (9) CARBOXYLIC ACIDS, ESTERS, AMINES, AND AMIDES

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

More information

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.

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.

More information

Experiment #8 properties of Alcohols and Phenols

Experiment #8 properties of Alcohols and Phenols Introduction Experiment #8 properties of Alcohols and Phenols As has been mentioned before, over 20 million organic compounds have been identified. If each substance had to be studied as an entity completely

More information

11.4 NUCLEOPHILIC SUBSTITUTION REACTIONS OF EPOXIDES

11.4 NUCLEOPHILIC SUBSTITUTION REACTIONS OF EPOXIDES .4 NUEPII SUBSTITUTIN REATINS F EPXIDES 495 (d When tert-butyl methyl ether is heated with sulfuric acid, methanol and -methylpropene distill from the solution. (e Tert-butyl methyl ether cleaves much

More information

Identification of Unknown Organic Compounds

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

More information

Survival Organic Chemistry Part I: Molecular Models

Survival Organic Chemistry Part I: Molecular Models Survival Organic Chemistry Part I: Molecular Models The goal in this laboratory experience is to get you so you can easily and quickly move between empirical formulas, molecular formulas, condensed formulas,

More information

Avg. 16.4 / 25 Stnd. Dev. 8.2

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

More information

SOLID SUPPORTS AND CATALYSTS IN ORGANIC SYNTHESIS

SOLID SUPPORTS AND CATALYSTS IN ORGANIC SYNTHESIS SOLID SUPPORTS AND CATALYSTS IN ORGANIC SYNTHESIS Editor Professor K. SMITH, M.SC,PhD. Head of Department of Chemistry University College of Swansea Wales ELLIS HORWOOD PTR PRENTICE HALL NEW YORK LONDON

More information

Unit 2 Review: Answers: Review for Organic Chemistry Unit Test

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)

More information

CHM220 Nucleophilic Substitution Lab. Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon*

CHM220 Nucleophilic Substitution Lab. Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon* CHM220 Nucleophilic Substitution Lab Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon* Purpose: To convert a primary alcohol to an alkyl bromide using an S N 2 reaction

More information

CH 3 CH 2 ONa + H 2 O. CH 3 CH 2 NH 2 + CH 3 OLi

CH 3 CH 2 ONa + H 2 O. CH 3 CH 2 NH 2 + CH 3 OLi rganic Chemistry Jasperse Acid- Practice Problems A. Identify each chemical as either an acid or a base in the following reactions, and identify conjugate relationships. -You should have one acid and one

More information

Amides and Amines: Organic Nitrogen Compounds

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,

More information

SULFONATE AND INORGANIC ESTER DERIVATIVES OF ALCOHOLS

SULFONATE AND INORGANIC ESTER DERIVATIVES OF ALCOHOLS 0. ULFNATE AND INRGANIC ETER DERIVATIVE F ALCL 44 R 2 C L CR 2 carbocation Lewis acid base association X (halide ion) 2 $ R 2 C L CR 2 R R X C A C $ alkyl halide R R alkene $ $ Brønsted acid base reaction

More information

Molecules, Compounds, and Chemical Equations (Chapter 3)

Molecules, Compounds, and Chemical Equations (Chapter 3) Molecules, Compounds, and Chemical Equations (Chapter 3) Chemical Compounds 1. Classification of Elements and Compounds Types of Pure Substances (Figure 3.4) Elements -- made up of only one type of atom

More information

SUBSTITUTION REACTION CHARACTERISTICS. Sn1: Substitution Nucleophilic, Unimolecular: Characteristics

SUBSTITUTION REACTION CHARACTERISTICS. Sn1: Substitution Nucleophilic, Unimolecular: Characteristics SUBSTITUTION EATION AATEISTIS Sn2: Substitution cleophilic, Bimolecular: haracteristics 1) The 2 means Bimolecular (or 2 nd order) in the rate-determining (slow) step: rate = k [: - ] [-X] or rate = k

More information

ORGANIC CHEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions

ORGANIC CHEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions ORGANIC CEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions 1) Which of the following best represents the carbon-chlorine bond of methyl chloride? d d - d - d d d d - d - I II III IV V 2) Provide a detailed,

More information

DETERMINACIÓN DE ESTRUCTURAS ORGÁNICAS (ORGANIC SPECTROSCOPY) IR SPECTROSCOPY

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

More information

Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution Electrophilic Aromatic Substitution Electrophilic Aromatic Substitution: a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring

More information

Balancing Chemical Equations

Balancing Chemical Equations Balancing Chemical Equations Academic Success Center Science Tutoring Area Science Tutoring Area Law of Conservation of Mass Matter cannot be created nor destroyed Therefore the number of each type of

More information

Chapter 10. Conjugation in Alkadienes and Allylic Systems. Class Notes. B. The allyl group is both a common name and an accepted IUPAC name

Chapter 10. Conjugation in Alkadienes and Allylic Systems. Class Notes. B. The allyl group is both a common name and an accepted IUPAC name Chapter 10 Conjugation in Alkadienes and Allylic Systems Chapter 10 suggested problems: I. The allyl group Class Notes A. B. The allyl group is both a common name and an accepted IUPAC name 1. Allyl alcohol

More information

IB Chemistry 1 Mole. One atom of C-12 has a mass of 12 amu. One mole of C-12 has a mass of 12 g. Grams we can use more easily.

IB Chemistry 1 Mole. One atom of C-12 has a mass of 12 amu. One mole of C-12 has a mass of 12 g. Grams we can use more easily. The Mole Atomic mass units and atoms are not convenient units to work with. The concept of the mole was invented. This was the number of atoms of carbon-12 that were needed to make 12 g of carbon. 1 mole

More information

EXPERIMENT 1: Survival Organic Chemistry: Molecular Models

EXPERIMENT 1: Survival Organic Chemistry: Molecular Models EXPERIMENT 1: Survival Organic Chemistry: Molecular Models Introduction: The goal in this laboratory experience is for you to easily and quickly move between empirical formulas, molecular formulas, condensed

More information

Write the acid-base equilibria connecting all components in the aqueous solution. Now list all of the species present.

Write the acid-base equilibria connecting all components in the aqueous solution. Now list all of the species present. Chapter 16 Acids and Bases Concept Check 16.1 Chemists in the seventeenth century discovered that the substance that gives red ants their irritating bite is an acid with the formula HCHO 2. They called

More information

Introduction to Biodiesel Chemistry Terms and Background Information

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

More information

Chapter 17. How are acids different from bases? Acid Physical properties. Base. Explaining the difference in properties of acids and bases

Chapter 17. How are acids different from bases? Acid Physical properties. Base. Explaining the difference in properties of acids and bases Chapter 17 Acids and Bases How are acids different from bases? Acid Physical properties Base Physical properties Tastes sour Tastes bitter Feels slippery or slimy Chemical properties Chemical properties

More information

Addition Reactions of Carbon-Carbon Pi Bonds - Part 1

Addition Reactions of Carbon-Carbon Pi Bonds - Part 1 Addition eactions of arbon-arbon Pi Bonds - Part 1 3 δ+ 2 δ 3 3 3 + 2 3 2 3 What Is an Addition eaction? Addition reaction: Atoms or groups are added to opposite ends of a pi bond. X Y Why should I study

More information

Amines H 3 C H. CH 2 CH 3 ethylmethylamine. Nomenclature. 1 o : RNH 2, 2 o : RR'NH, 3 o : RR'R"N, 4 o (salt) RR'R"R'"N + R = alkyl or aryl

Amines H 3 C H. CH 2 CH 3 ethylmethylamine. Nomenclature. 1 o : RNH 2, 2 o : RR'NH, 3 o : RR'RN, 4 o (salt) RR'RR'N + R = alkyl or aryl Amines omenclature 1 o :, 2 o : 'H, 3 o : '", 4 o (salt) '"'" + = alkyl or aryl ommon names For simple amines name groups attached to alphabetically; use suffix -amine. H 3 H H 2 ethylmethylamine In complicated

More information

Organic Functional Groups Chapter 7. Alcohols, Ethers and More

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

More information

Chapter 7 Substitution Reactions

Chapter 7 Substitution Reactions Chapter 7 Substitution Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 7. Each of the sentences below appears

More information

Writing and Balancing Chemical Equations

Writing and Balancing Chemical Equations Name Writing and Balancing Chemical Equations Period When a substance undergoes a chemical reaction, chemical bonds are broken and new bonds are formed. This results in one or more new substances, often

More information

Boston University Dresden Science Program ORGANIC CHEMISTRY CAS CH 203 Lecture

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:

More information

Synthesis of Isopentyl Acetate

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

More information

Copyright 2010 Pearson Education, Inc. Chapter Fourteen 1

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,

More information

p3 Recognizing Acid/Base Properties when p11 Recognizing Basic versus Nonbasic

p3 Recognizing Acid/Base Properties when p11 Recognizing Basic versus Nonbasic General Chemistry II Jasperse Acid-Base Chemistry. Extra Practice Problems 1 General Types/Groups of problems: Conceptual Questions. Acids, Bases, and p1 K b and pk b, Base Strength, and using K b or p7-10

More information

Infrared Spectroscopy 紅 外 線 光 譜 儀

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

More information

INCOMPATIBILITY OF COMMON LABORATORY CHEMICALS

INCOMPATIBILITY OF COMMON LABORATORY CHEMICALS INCOMPATIBILITY OF COMMON LABORATORY CHEMICALS When certain hazardous chemicals are stored or mixed together, violent reactions may occur because the chemicals are unsuitable for mixing, or are incompatible.

More information

Reactions of Aldehydes and Ketones

Reactions of Aldehydes and Ketones Reactions of Aldehydes and Ketones Structure Deduction using lassification Tests 1 Determination of Structure Determining the structure of an unknown organic compound is an exercise in deductive reasoning.

More information

Reactions of Fats and Fatty Acids

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

More information

Stoichiometry Review

Stoichiometry Review Stoichiometry Review There are 20 problems in this review set. Answers, including problem set-up, can be found in the second half of this document. 1. N 2 (g) + 3H 2 (g) --------> 2NH 3 (g) a. nitrogen

More information

Chapter 8: Chemical Equations and Reactions

Chapter 8: Chemical Equations and Reactions Chapter 8: Chemical Equations and Reactions I. Describing Chemical Reactions A. A chemical reaction is the process by which one or more substances are changed into one or more different substances. A chemical

More information

Chapter 14 - Acids and Bases

Chapter 14 - Acids and Bases Chapter 14 - Acids and Bases 14.1 The Nature of Acids and Bases A. Arrhenius Model 1. Acids produce hydrogen ions in aqueous solutions 2. Bases produce hydroxide ions in aqueous solutions B. Bronsted-Lowry

More information

Chemistry Post-Enrolment Worksheet

Chemistry Post-Enrolment Worksheet Name: Chemistry Post-Enrolment Worksheet The purpose of this worksheet is to get you to recap some of the fundamental concepts that you studied at GCSE and introduce some of the concepts that will be part

More information

Chemistry: Chemical Equations

Chemistry: Chemical Equations Chemistry: Chemical Equations Write a balanced chemical equation for each word equation. Include the phase of each substance in the equation. Classify the reaction as synthesis, decomposition, single replacement,

More information

SUMMARY OF ALKENE REACTIONS

SUMMARY OF ALKENE REACTIONS SUMMARY F ALKENE REACTINS Alkenes are primarily prepared by elimination reactions of molecules that contain good leaving groups attached to sp 3 carbons. Examples of such reactions are dehydrohalogenations

More information

Benzene Benzene is best represented as a resonance hybrid:

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

More information

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 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

More information

Determining the Structure of an Organic Compound

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

More information

Chemical Basis of Life Module A Anchor 2

Chemical Basis of Life Module A Anchor 2 Chemical Basis of Life Module A Anchor 2 Key Concepts: - Water is a polar molecule. Therefore, it is able to form multiple hydrogen bonds, which account for many of its special properties. - Water s polarity

More information

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)

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

More information

WRITING CHEMICAL FORMULA

WRITING CHEMICAL FORMULA WRITING CHEMICAL FORMULA For ionic compounds, the chemical formula must be worked out. You will no longer have the list of ions in the exam (like at GCSE). Instead you must learn some and work out others.

More information

Molecular Formula Determination

Molecular Formula Determination Molecular Formula Determination Classical Approach Qualitative elemental analysis Quantitative elemental analysis Determination of empirical formula Molecular weight determination Molecular formula determination

More information

Chem 1100 Chapter Three Study Guide Answers Outline I. Molar Mass and Moles A. Calculations of Molar Masses

Chem 1100 Chapter Three Study Guide Answers Outline I. Molar Mass and Moles A. Calculations of Molar Masses Chem 1100 Chapter Three Study Guide Answers Outline I. Molar Mass and Moles A. Calculations of Molar Masses B. Calculations of moles C. Calculations of number of atoms from moles/molar masses 1. Avagadro

More information

Laboratory 22: Properties of Alcohols

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,

More information

6) Which compound is manufactured in larger quantities in the U.S. than any other industrial chemical?

6) Which compound is manufactured in larger quantities in the U.S. than any other industrial chemical? MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Which statement concerning Arrhenius acid-base theory is not correct? A) Acid-base reactions must

More information

Chapter 2 The Chemical Context of Life

Chapter 2 The Chemical Context of Life Chapter 2 The Chemical Context of Life Multiple-Choice Questions 1) About 25 of the 92 natural elements are known to be essential to life. Which four of these 25 elements make up approximately 96% of living

More information

1. The functional group present in carboxylic acids is called a A) carbonyl group. B) carboxyl group. C) carboxylate group. D) carbohydroxyl group.

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

More information

MOLECULAR REPRESENTATIONS AND INFRARED SPECTROSCOPY

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

More information

Question Bank Electrolysis

Question Bank Electrolysis Question Bank Electrolysis 1. (a) What do you understand by the terms (i) electrolytes (ii) non-electrolytes? (b) Arrange electrolytes and non-electrolytes from the following substances (i) sugar solution

More information

PART I: MULTIPLE CHOICE (30 multiple choice questions. Each multiple choice question is worth 2 points)

PART I: MULTIPLE CHOICE (30 multiple choice questions. Each multiple choice question is worth 2 points) CHEMISTRY 123-07 Midterm #1 Answer key October 14, 2010 Statistics: Average: 74 p (74%); Highest: 97 p (95%); Lowest: 33 p (33%) Number of students performing at or above average: 67 (57%) Number of students

More information

Chemistry Grade 11 Year and weekly plan 2015

Chemistry Grade 11 Year and weekly plan 2015 Chemistry Grade 11 Year and weekly plan 2015 TERM1 Content Curriculum Statement Teaching Method Atomic combinations: molecular structure chemical bond (is seen as the net electrostatic force two atoms

More information

partial positive an acid is a hydrogen ion donor, or proton donor base is a hydrogen ion acceptor, or proton acceptor acidic protons acid base

partial positive an acid is a hydrogen ion donor, or proton donor base is a hydrogen ion acceptor, or proton acceptor acidic protons acid base INTRDUCTIN T INIC MECANISMS PART I: FUNDAMENTALS F BRNSTED-LWRY ACID-BASE CEMISTRY YDRGEN ATMS AND PRTNS IN RGANIC MLECULES - A hydrogen atom that has lost its only electron is sometimes referred to as

More information

CHEM 203 Exam 1. KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question.

CHEM 203 Exam 1. KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question. CHEM 203 Exam 1 KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question. _D C 1. Which of the following elements is a large percentage of both

More information

Oxidation of Cyclohexanol to Cyclohexanone

Oxidation of Cyclohexanol to Cyclohexanone Reminder: These notes are meant to supplement, not replace, the laboratory manual. Oxidation of Cyclohexanol to Cyclohexanone History and Application: Oxidation reactions are incredibly important in the

More information