CHEM 263 Oct 25, stronger base stronger acid weaker acid weaker base

Size: px
Start display at page:

Download "CHEM 263 Oct 25, stronger base stronger acid weaker acid weaker base"

Transcription

1 CEM 263 ct 25, 2016 Reactions and Synthesis (Preparation) of R- Breaking the - Bond of R- with Metals R + Li 0 or Na 0 or K 0 metal R Li + 1/2 2 alkoxide Breaking the - Bond of R- by Acid-Base Reaction Examples: Na C 2 C Na + C 3 C 2 strong base sodium ethoxide pk a 16 strong acid weak base pk a 17 weak acid K K strong base pk a 16 strong acid pk a 19 weak acid weak base C 3 Na C 3 Na pka=10 pka=16 stronger base stronger acid weaker acid weaker base Preparation of Alcohols and Ethers from Alkanes Substitution reaction Alkane X 2 h! Elimination reaction Alkyl halide Base Alkene R' R'K R' =, alkyl -R, - Addition reaction R--R' alcohol or ether

2 Example: Br 2 h! Br 2 eat S N 1 Substitution reaction Br K E 1 or E 2 2 Br K (hindered base) Elimination reaction E S Addition reaction 4 + KBr + Preparation of Alcohols and Ethers from Alkenes 2 S 4 Markovnikov Addition C 3 C 3 Mechanism: C 3 3 C C 3 The alkene is first protonated to give a tertiary carbocation, which is then attacked by a lone pair on the oxygen of methanol. This is an intermolecular ether formation, where the reaction occurs between two molecules. 2 2 S S 4 Cineol - seed germination inhibitor Above is and addition of water to limonene, followed by an intramolecular ether formation, where the reaction occurs within the molecule to give cineol. The high local concentration of the reacting groups and the formation of a six-membered ring drive the reaction forward.

3 Mechanism: - + Markovnikov / Anti-Markovnikov Addition: 2 S 4?? = 1. B , Na B 2 6 behaves like B 3, which is a Lewis acid: B The first step of this last example is called hydroboration (syn addition), while the second is an oxidation. This is an example of anti-markovnikov addition. Mechanism: B B B 2 B 2 2 Na 3 B Anti-Markovnikov addition of water with retention of configuration + present in it's salt form in basic condition Borane adds to the least substituted carbon to give the more stable carbocation Syn addition of borane and Na is used for deprotonation of hydrogen peroxide replaces boron with retention of stereochemistry

4 Examples: 1) B 2 6 2) 2 2, Na 1) B 2 6 2) 2 2, Na Note the cis-addition of 2. Preparation of Ethers from Alkenes Epoxidation epoxides can be opened by water 2 ethylene oxide Epoxide formation: 3 C C an epoxide aka oxirane 3 membered ether ring It is a concerted and stereospecific reaction 3 C C formed as racemate (racemic mixture = 1:1 mix of enantiomers) Concerted mechanism: C3

5 Examples: 3 C C formed as racemate (racemic mixture = 1:1 mix of enantiomers) 3 C C formed as single compound (meso compound = achiral but has stereocentres) Note that achiral starting material and (achiral) gives a net achiral product(s). That is, the products are either racemic, or a meso compound. Examples: Is the product of the following reaction one enantiomer or racemic? (racemic reagent equally likely to approach from the top or bottom) C 3 C 3 Disparlure = sex pheromone of Gypsy Moth C 2 human cells C 2 2 Cyclooxygenase Arachidonic Acid = all Z 5,8,11,14-eicosatetraenoic acid Leukotriene A 4 Leukotriene A 4 is an inflammatory signal for asthma and allergic reactions.

6 Alcohols and Ethers from Alkyl alides R-X R R-X RR X = Cl, Br, I, S 2 R Substitution reactions (S N 2, S N 1) S = Substitution N = Nucleophilic 2 or 1 = rate depends on 2 concentrations or 1 concentration S N 2 or - R X R Stereospecific (the stereochemistry of the reactants determines the stereochemistry of the products) Inversion of configuration (Walden Inversion) Concerted (bonds are broken and formed at the same time) Bimolecular 1 halides work the best 2 halides work ok 3 halides don t work In general C=C-X (vinyl halides) also fail for this type of reaction Example: 3 C I + Na C 3 + NaI This is not reversible, because I- is more stable than - Would the following reaction occur? I Na No, this involves a tertiary halide, which is too crowded. Elimination could occur though, to produce:

7 What reagents instead of Na could be used that would allow the above substitution reaction to occur? Answer: 2, 2 S 4 and heat would allow an S N 1 reaction to occur: I 2 2 S 4 heat 2

Chapter 11 - Alcohols and Ethers 1

Chapter 11 - Alcohols and Ethers 1 Andrew Rosen Chapter 11 - Alcohols and Ethers 1 11.1 - Structure and Nomenclature - The common naming calls alcohols as alkyl alcohols (eg: methyl alcohol) - The common names of ethers have the groups

More information

Alcohols, Ethers, & Epoxides

Alcohols, Ethers, & Epoxides Alcohols, Ethers, & Epoxides Alcohols Structure and Bonding Enols and Phenols Compounds having a hydroxy group on a sp 2 hybridized carbon enols and phenols undergo different reactions than alcohols. Chapter

More information

REACTION AND SYNTHESIS REVIEW

REACTION AND SYNTHESIS REVIEW REACTION AND SYNTHESIS REVIEW A STUDENT SHOULD BE ABLE TO PREDICT PRODUCTS, IDENTIFY REACTANTS, GIVE REACTION CONDITIONS, PROPOSE SYNTHESES, AND PROPOSE MECHANISMS (AS LISTED BELOW). REVIEW THE MECHANISM

More information

2/26/18. Practice Questions. Practice Questions B F. How many steps are there in this reaction?

2/26/18. Practice Questions. Practice Questions B F. How many steps are there in this reaction? Practice Questions Practice Questions D B F C E A G How many steps are there in this reaction? 1 Practice Questions D B F C E A G What is the highest-energy transitions state? Practice Questions D B F

More information

Chapter 8 Alkenes and Alkynes II: Addition Reactions. Alkenes are electron rich. Additions to Alkenes

Chapter 8 Alkenes and Alkynes II: Addition Reactions. Alkenes are electron rich. Additions to Alkenes Additions to Alkenes Chapter 8 Alkenes and Alkynes II: Addition Reactions Generally the reaction is exothermic because one p and one s bond are converted to two s bonds Alkenes are electron rich The carbocation

More information

OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2018

OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2018 OChem 1 Mechanism Flashcards Dr. Peter Norris, 2018 Mechanism Basics Chemical change involves bonds forming and breaking; a mechanism describes those changes using curved arrows to describe the electrons

More information

1. Radical Substitution on Alkanes. 2. Radical Substitution with Alkenes. 3. Electrophilic Addition

1. Radical Substitution on Alkanes. 2. Radical Substitution with Alkenes. 3. Electrophilic Addition 1. Radical Substitution on Alkanes Only Cl and Br are useful at the laboratory level. Alkane reactivity: tertiary > secondary > primary > methyl Numbers below products give their relative yield. Relative

More information

Preparation of alkenes

Preparation of alkenes Lecture 11 אלקנים הכנה ותגובות של אלקנים: הידרוגנציה, סיפוח הידרוהלוגנים )כלל מארקובניקוב(, סיפוח הלוגנים והסטראוכימיה של תוצרי הסיפוח, הידרובורציה, אפוקסידציה, אוזונוליזה. 1 Preparation of alkenes 1.

More information

Chapter 8 Alkenes and Alkynes II: Addition Reactions

Chapter 8 Alkenes and Alkynes II: Addition Reactions Chapter 8 Alkenes and Alkynes II: Addition Reactions Introduction: Additions to Alkenes Generally the reaction is exothermic because one π and one σ bond are converted to two σ bonds The π electrons of

More information

Chapter 8 Alkenes and Alkynes II: Addition Reactions "

Chapter 8 Alkenes and Alkynes II: Addition Reactions Chapter 8 Alkenes and Alkynes II: Addition Reactions Additions to Alkenes Generally the reaction is exothermic because one π and one σ bond are converted to two σ bonds Alkenes are electron rich The π

More information

Chapter 10 Lecture Outline

Chapter 10 Lecture Outline Organic Chemistry, Fifth Edition Janice Gorzynski Smith University of Hawai i Chapter 10 Lecture Outline Modified by Dr. Juliet Hahn Copyright 2017 McGraw-Hill Education. All rights reserved. No reproduction

More information

Chapter 7 Substitution Reactions 7.1 Introduction to Substitution Reactions Substitution Reactions: two reactants exchange parts to give new products

Chapter 7 Substitution Reactions 7.1 Introduction to Substitution Reactions Substitution Reactions: two reactants exchange parts to give new products hapter 7 Substitution eactions 7.1 Introduction to Substitution eactions Substitution eactions: two reactants exchange parts to give new products A-B + -D A-D + B- 3 2 + Br 3 2 Br + Elimination eaction:

More information

Organic Chemistry, Second Edition. Janice Gorzynski Smith University of Hawai i. Chapter 10 Alkenes

Organic Chemistry, Second Edition. Janice Gorzynski Smith University of Hawai i. Chapter 10 Alkenes Organic Chemistry, Second Edition Janice Gorzynski Smith University of Hawai i Chapter 10 Alkenes Prepared by Rabi Ann Musah State University of New York at Albany Copyright The McGraw-Hill Companies,

More information

Alcohol Synthesis. Dr. Sapna Gupta

Alcohol Synthesis. Dr. Sapna Gupta Alcohol Synthesis Dr. Sapna Gupta Synthesis of Alcohols Alcohols can be synthesized from several functional groups. Nucleophilic substitution of O - on alkyl halide ydration of alkenes water in acid solution

More information

Ethers can be symmetrical or not:

Ethers can be symmetrical or not: Chapter 14: Ethers, Epoxides, and Sulfides 175 Physical Properties Ethers can be symmetrical or not: linear or cyclic. Ethers are inert and make excellent solvents for organic reactions. Epoxides are very

More information

Chapter 8: Nucleophilic Substitution 8.1: Functional Group Transformation By Nucleophilic Substitution

Chapter 8: Nucleophilic Substitution 8.1: Functional Group Transformation By Nucleophilic Substitution hapter 8: Nucleophilic Substitution 8.1: Functional Group Transformation By Nucleophilic Substitution Nu: = l,, I Nu - Nucleophiles are Lewis bases (electron-pair donor) Nucleophiles are often negatively

More information

CHEM Lecture 7

CHEM Lecture 7 CEM 494 Special Topics in Chemistry Illinois at Chicago CEM 494 - Lecture 7 Prof. Duncan Wardrop ctober 22, 2012 CEM 494 Special Topics in Chemistry Illinois at Chicago Preparation of Alkenes Elimination

More information

Homework - Review of Chem 2310

Homework - Review of Chem 2310 omework - Review of Chem 2310 Chapter 1 - Atoms and Molecules Name 1. What is organic chemistry? 2. Why is there an entire one year course devoted to the study of organic compounds? 3. Give 4 examples

More information

Basic Organic Chemistry Course code : CHEM (Pre-requisites : CHEM 11122)

Basic Organic Chemistry Course code : CHEM (Pre-requisites : CHEM 11122) Basic Organic Chemistry Course code : CHEM 12162 (Pre-requisites : CHEM 11122) Chapter 01 Mechanistic Aspects of S N2,S N1, E 2 & E 1 Reactions Dr. Dinesh R. Pandithavidana Office: B1 222/3 Phone: (+94)777-745-720

More information

Organic Reactions Susbstitution S N. Dr. Sapna Gupta

Organic Reactions Susbstitution S N. Dr. Sapna Gupta Organic Reactions Susbstitution S N 2 Dr. Sapna Gupta Kinetics of Nucleophilic Reaction Rate law is order of reaction 0 order is when rate of reaction is unaffected by change in concentration of the reactants

More information

OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2015

OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2015 OChem 1 Mechanism Flashcards Dr. Peter Norris, 2015 Mechanism Basics Chemical change involves bonds forming and breaking; a mechanism describes those changes using curved arrows to describe the electrons

More information

11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations Based on McMurry s Organic Chemistry, 6 th edition 2003 Ronald Kluger Department of Chemistry University of Toronto Alkyl Halides

More information

Hydrogen iodide is a strong acid and will drive the reverse reaction, meaning the forward reaction will not occur.

Hydrogen iodide is a strong acid and will drive the reverse reaction, meaning the forward reaction will not occur. EM 261 Oct 18, 2018 Photosynthesis and Related Reactions O 2 2 O 6 12 O 6 2 O N 3, S, Fe, u, o, other Natural Products D-Glucose R O R OR Ionic substitution S N 1 & R X X 2 hv Petroleum/ Alkanes R N 2

More information

Preparation of Alkyl Halides, R-X. Reaction of alkanes with Cl 2 & Br 2 (F 2 is too reactive, I 2 is unreactive): R + X X 2.

Preparation of Alkyl Halides, R-X. Reaction of alkanes with Cl 2 & Br 2 (F 2 is too reactive, I 2 is unreactive): R + X X 2. Preparation of Alkyl alides, R-X Reaction of alkanes with Cl 2 & Br 2 (F 2 is too reactive, I 2 is unreactive): UV R + X 2 R X or heat + X This mechanism involves a free radical chain reaction. A chain

More information

1.13 Acid-Base Reactions: Lone-Pair Donors & Acceptors

1.13 Acid-Base Reactions: Lone-Pair Donors & Acceptors 1.13 Acid-Base Reactions: Lone-Pair Donors & Acceptors I, Cl, N 3, 3 P 4 pka 10 to 5 Super strong acids 3 + pka 1.7 RC 2 pka ~ 5 acids Ph pka ~ 10 get 2, R pka ~ 16 weaker RCC (alkynes) pka ~ 26 RN 2 pka

More information

LECTURE #14 Thurs., Oct.20, Midterm exam: Tues.Oct.25 during class Ch.1, , 7.10, 2, Sections

LECTURE #14 Thurs., Oct.20, Midterm exam: Tues.Oct.25 during class Ch.1, , 7.10, 2, Sections CHEM 221 section 01 LECTURE #14 Thurs., Oct.20, 2005 Midterm exam: Tues.Oct.25 during class Ch.1, 7.2-7.5, 7.10, 2, 3.1-3.5 ASSIGNED READINGS: TODAY S CLASS: NEXT LECTURE: Sections 4.7-4.10 finish Ch.4,

More information

Chapter 8 Reactions of Alkenes

Chapter 8 Reactions of Alkenes Chapter 8 Reactions of Alkenes Electrophilic Additions o Regio vs stereoselectivity Regio where do the pieces add? Markovnikov s rule hydrogen will go to the side of the double bond with most hydrogens.

More information

REACTIONS OF HALOALKANES - SUBSTITUTION AND ELIMINATION

REACTIONS OF HALOALKANES - SUBSTITUTION AND ELIMINATION REACTIONS OF HALOALKANES - SUBSTITUTION AND ELIMINATION Haloalkanes (also known as halogenoalkanes and alkyl halides) are organic compounds where one of the hydrogens of an alkane or cycloalkane has been

More information

Chemistry 35 Exam 2 Answers - April 9, 2007

Chemistry 35 Exam 2 Answers - April 9, 2007 Chemistry 35 Exam 2 Answers - April 9, 2007 Problem 1. (14 points) Provide the products for the reactions shown below. If stereochemistry is important, be sure to indicate stereochemistry clearly. If no

More information

Alcohols: Contain a hydroxy group( OH) bonded to an sp 2 or sp 3 hybridized

Alcohols: Contain a hydroxy group( OH) bonded to an sp 2 or sp 3 hybridized Lecture Notes hem 51B S. King hapter 9 Alcohols, Ethers, and Epoxides I. Introduction Alcohols, ether, and epoxides are 3 functional groups that contain σ-bonds. Alcohols: ontain a hydroxy group( ) bonded

More information

Organic Chemistry Lecture 2 - Hydrocarbons, Alcohols, Substitutions

Organic Chemistry Lecture 2 - Hydrocarbons, Alcohols, Substitutions ALKANES Water-insoluble, low density C-C single bonds Higher MW -> higher BP, higher MP Branching -> lower BP, higher MP Forms cycloalkanes which can have ring strain Cyclohexane: chair vs. boat configuration

More information

Chapter 4. Reactions of alkenes. Addition reactions Carbocations Selectivity of reactions

Chapter 4. Reactions of alkenes. Addition reactions Carbocations Selectivity of reactions Chapter 4 Reactions of alkenes Addition reactions Carbocations Selectivity of reactions Prob 47 p192. Give the reagents that would be required (including catalyst). Ch 4 #2 Electrophilic addition Ch 4

More information

Chapter 8: Ethers and Epoxides. Diethyl ether in starting fluid

Chapter 8: Ethers and Epoxides. Diethyl ether in starting fluid Chapter 8: Ethers and Epoxides Diethyl ether in starting fluid 8.1 Nomenclature of Ethers Ethers are usually named by giving the name of each alkyl or aryl group, in alphabetical order, followed by the

More information

Elimination Reactions Heating an alkyl halide with a strong base causes elimination of a. molecule of HX

Elimination Reactions Heating an alkyl halide with a strong base causes elimination of a. molecule of HX Elimination eactions eating an alkyl halide with a strong base causes elimination of a molecule of X 1. Potassium hydroxide dissolved in ethanol and the sodium salts of alcohols (such as sodium ethoxide)

More information

7. Haloalkanes (text )

7. Haloalkanes (text ) 2009, Department of hemistry, The University of Western Ontario 7.1 7. aloalkanes (text 7.1 7.10) A. Structure and Nomenclature Like hydrogen, the halogens have a valence of one. Thus, a halogen atom can

More information

Ethers. Synthesis of Ethers. Chemical Properties of Ethers

Ethers. Synthesis of Ethers. Chemical Properties of Ethers Page 1 of 6 like alcohols are organic derivatives of water, but lack the labile -OH group. As a result, ethers, except for epoxides, are usually not very reactive and are often used as solvents for organic

More information

b.p.=100 C b.p.=65 C b.p.=-25 C µ=1.69 D µ=2.0 D µ=1.3 D

b.p.=100 C b.p.=65 C b.p.=-25 C µ=1.69 D µ=2.0 D µ=1.3 D Alcohols I eading: Wade chapter 10, sections 10-1- 10-12 Study Problems: 10-35, 10-37, 10-38, 10-39, 10-40, 10-42, 10-43 Key Concepts and Skills: Show how to convert alkenes, alkyl halides, and and carbonyl

More information

Chem 3719 Example Exams. Chemistry 3719 Practice Exams

Chem 3719 Example Exams. Chemistry 3719 Practice Exams Chem 3719 Example Exams Chemistry 3719 Practice Exams Fall 2018 Chemistry 3719, Fall 2017 Exam 1 Student Name: Y Number: This exam is worth 100 points out of a total of 700 points for Chemistry 3719/3719L.

More information

Double and Triple Bonds. The addition of an electrophile and a

Double and Triple Bonds. The addition of an electrophile and a Chapter 11 Additions to Carbon-Carbon Double and Triple Bonds The addition of an electrophile and a nucleophile to a C-C C double or triple bonds 11.1 The General Mechanism Pi electrons of the double bond

More information

Chapter 9. Nucleophilic Substitution and ß-Elimination

Chapter 9. Nucleophilic Substitution and ß-Elimination Chapter 9 Nucleophilic Substitution and ß-Elimination Nucleophilic Substitution Nucleophile: From the Greek meaning nucleus loving. A molecule or ion that donates a pair of electrons to another atom or

More information

Chapter 6 Ionic Reactions-Nucleophilic Substitution and Elimination Reactions of Alkyl Halides"

Chapter 6 Ionic Reactions-Nucleophilic Substitution and Elimination Reactions of Alkyl Halides Chapter 6 Ionic Reactions-Nucleophilic Substitution and Elimination Reactions of Alkyl Halides" t Introduction" The polarity of a carbon-halogen bond leads to the carbon having a partial positive charge"

More information

ELECTROPHILIC ADDITIONS OF ALKENES AS THE COUNTERPART OF ELIMINATIONS

ELECTROPHILIC ADDITIONS OF ALKENES AS THE COUNTERPART OF ELIMINATIONS ELECTRPHILIC ADDITINS F ALKENES AS THE CUNTERPART F ELIMINATINS INTRDUCTIN - Chapter 8 is mostly about alkene reactions. That is, how one can transform alkenes into other functional groups. Most of these

More information

CHAPTER 7. Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

CHAPTER 7. Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination CHAPTER 7 Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination 7-1 Solvolysis of Tertiary and Secondary Haloalkanes The rate of S N 2 reactions decrease dramatically

More information

Chapter 8 Alkenes and Alkynes II: Addition Reactions. Alkenes are electron rich. Additions to Alkenes

Chapter 8 Alkenes and Alkynes II: Addition Reactions. Alkenes are electron rich. Additions to Alkenes Additions to Alkenes hapter 8 Alkenes and Alkynes II: Addition eactions Generally the reaction is exothermic because one π and one σ bond are converted to two σ bonds Alkenes are electron rich The carbocation

More information

CH Organic Chemistry I (Katz) Practice Exam #3- Fall 2013

CH Organic Chemistry I (Katz) Practice Exam #3- Fall 2013 C2710 - rganic Chemistry I (Katz) Practice Exam #3- all 2013 Name: Score: Part I - Choose the best answer and write the letter of your choice in the space provided. (32 pts) 1. f the following, which reaction

More information

Nuggets of Knowledge for Chapter 12 Alkenes (II) Chem reaction what is added to the C=C what kind of molecule results addition of HX HX only

Nuggets of Knowledge for Chapter 12 Alkenes (II) Chem reaction what is added to the C=C what kind of molecule results addition of HX HX only I. Addition Reactions of Alkenes Introduction Nuggets of Knowledge for Chapter 12 Alkenes (II) Chem 2310 An addition reaction always involves changing a double bond to a single bond and adding a new bond

More information

Chapter 11 Outline: Ethers, Epoxides & Sulfides

Chapter 11 Outline: Ethers, Epoxides & Sulfides Chapter 11 Outline: Ethers, Epoxides & Sulfides Review Nomenclature & Physical Properties on your own 1. Structure of Ethers & Epoxides 2. Preparation of Ethers & Thioethers 3. Reactions of Ethers 4. Preparation

More information

Alkenes (Olefins) Chapters 7 & 8 Organic Chemistry, 8 th Edition John McMurry

Alkenes (Olefins) Chapters 7 & 8 Organic Chemistry, 8 th Edition John McMurry Alkenes (Olefins) Chapters 7 & 8 Organic Chemistry, 8 th Edition John McMurry 1 Structure and Bonding 2 Structure and Bonding Rotation around the C=C bond is restricted 90 rotation The p orbitals are orthogonal

More information

(Neither an oxidation or reduction: Addition or loss of H +, H 2 O, HX).

(Neither an oxidation or reduction: Addition or loss of H +, H 2 O, HX). eactions 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. xidation is a

More information

Hyperlearning MCAT Instructor Qualifying Exam Organic Chemistry

Hyperlearning MCAT Instructor Qualifying Exam Organic Chemistry Hyperlearning MCAT Instructor Qualifying Exam Organic Chemistry 30 Questions (5 pages); Time limit = 45 minutes Use of books or notes is not permitted. 1. When analyzed with a polarimeter, which of the

More information

Electrophilic Addition

Electrophilic Addition . Reactivity of = Electrons in pi bond are loosely held. Electrophiles are attracted to the pi electrons. arbocation intermediate forms. Nucleophile adds to the carbocation. Net result is addition to the

More information

Chapter 7. Alkenes: Reactions and Synthesis

Chapter 7. Alkenes: Reactions and Synthesis Chapter 7. Alkenes: Reactions and Synthesis 1 Synthesis of Alkenes: Elimination Reactions 1. Dehydrohalogenation of alkyl halides. loss of requires CH 2 CH 2 Cl Zaitsev s Rule: CH 2 C 2. Dehydration of

More information

Organic Halogen Compounds

Organic Halogen Compounds 8 Organic alogen ompounds APTER SUMMARY 8.1 Introduction Although organic halogen compounds are rarely found in nature, they do have a variety of commercial applications including use as insecticides,

More information

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

75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will

75. 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 information

BSc. II 3 rd Semester. Submitted By Dr. Sangita Nohria Associate Professor PGGCG-11 Chandigarh 1

BSc. II 3 rd Semester. Submitted By Dr. Sangita Nohria Associate Professor PGGCG-11 Chandigarh 1 BSc. II 3 rd Semester Submitted By Dr. Sangita Nohria Associate Professor PGGCG-11 Chandigarh 1 Introduction to Alkyl Halides Alkyl halides are organic molecules containing a halogen atom bonded to an

More information

Chapter 15: Conjugated Systems, Orbital Symmetry, and UV Spectroscopy

Chapter 15: Conjugated Systems, Orbital Symmetry, and UV Spectroscopy Chapter 15: Conjugated Systems, Orbital Symmetry, and UV Spectroscopy Conjugated unsaturated systems have a p orbital on a carbon adjacent to a double bond The p orbital can come from another double (e.g.

More information

Organic Chemistry. Alkenes (2)

Organic Chemistry. Alkenes (2) For updated version, please click on http://ocw.ump.edu.my Organic Chemistry Alkenes (2) by Dr. Seema Zareen & Dr. Izan Izwan Misnon Faculty Industrial Science & Technology seema@ump.edu.my & iezwan@ump.edu.my

More information

10. Organohalides. Based on McMurry s Organic Chemistry, 7 th edition

10. Organohalides. Based on McMurry s Organic Chemistry, 7 th edition 10. Organohalides Based on McMurry s Organic Chemistry, 7 th edition What Is an Alkyl Halide An organic compound containing at least one carbonhalogen bond (C-X) X (F, Cl, Br, I) replaces H Can contain

More information

Chapter 11: Nucleophilic Substitution and Elimination Walden Inversion

Chapter 11: Nucleophilic Substitution and Elimination Walden Inversion hapter 11: Nucleophilic Substitution and Elimination Walden Inversion (S)-(-) Malic acid [a] D = -2.3 Ag 2, 2 Pl 5 l Ag 2, 2 ()-2-hlorosuccinic acid l (-)-2-hlorosuccinic acid Pl 5 ()-() Malic acid [a]

More information

Chapter 6: Organic Halogen Compounds; Substitution and Elimination Reactions

Chapter 6: Organic Halogen Compounds; Substitution and Elimination Reactions Chapter 6: Organic Halogen Compounds; Substitution and Elimination Reactions Halogen compounds are important for several reasons. Simple alkyl and aryl halides, especially chlorides and bromides, are versatile

More information

CHE 275 NUCLEOPHILIC SUBSTITUTUION CHAP 8 ASSIGN. 1. Which best depicts the partial charges on methyl bromide and sodium methoxide?

CHE 275 NUCLEOPHILIC SUBSTITUTUION CHAP 8 ASSIGN. 1. Which best depicts the partial charges on methyl bromide and sodium methoxide? CHE 275 NUCLEPHILIC SUBSTITUTUIN CHAP 8 ASSIGN 1. Which best depicts the partial charges on methyl bromide and sodium methoxide? 2. Which of the following would be the best (most reactive) nucleophile

More information

REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2)

REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2) REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2) 1.) Why do haloalkenes under go nucleophillic substitution whereas haloarenes under go electophillic substitution. Ans. Due to more electro negative

More information

Elimination reactions

Elimination reactions Chapter 9 Elimination reactions E2 and E1 reactions Competition between S N and E Elimination reactions Ch 9 #2 elimination and/or substitution 2 mechanisms ~ E2 and E1 E2: bimolecular elimination rxn

More information

Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides

Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides Learning objectives: 1. Provide both IUPAC and common (when applicable) names for alcohols and ethers. 2. Describe the physical properties

More information

CHEM J-10 June The structure of ( )-linalool, a commonly occurring natural product, is shown below.

CHEM J-10 June The structure of ( )-linalool, a commonly occurring natural product, is shown below. CEM1102 2014-J-10 June 2014 The structure of ( )-linalool, a commonly occurring natural product, is shown below. 4 What is the molecular formula of ( )-linalool? C 10 18 O Which of the following best describes

More information

Chapter 8. Alkenes and Alkynes II: Addition Reactions. Ch. 8-1

Chapter 8. Alkenes and Alkynes II: Addition Reactions. Ch. 8-1 hapter 8 Alkenes and Alkynes II: Addition Reactions h. 8-1 1. Addition Reactions of Alkenes E + E Nu Nu h. 8-2 1A. ow To Understand Additions to Alkenes This is an addition reaction: E Nu added across

More information

Organic Chemistry CHM 314 Dr. Laurie S. Starkey, Cal Poly Pomona Alkyl Halides: Substitution Reactions - Chapter 6 (Wade)

Organic Chemistry CHM 314 Dr. Laurie S. Starkey, Cal Poly Pomona Alkyl Halides: Substitution Reactions - Chapter 6 (Wade) rganic Chemistry CM 314 Dr. Laurie S. Starkey, Cal Poly Pomona Alkyl alides: Substitution Reactions - Chapter 6 (Wade) Chapter utline I. Intro to RX (6-1 - 6-7) II. Substitution Reactions A) S N 2 (6-8,

More information

Classes of Halides. Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination. Polarity and Reactivity. Classes of Alkyl Halides

Classes of Halides. Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination. Polarity and Reactivity. Classes of Alkyl Halides rganic hemistry, 5 th Edition L. G. Wade, Jr. hapter 6 Alkyl alides: Nucleophilic Substitution and Elimination lasses of alides Alkyl: alogen, X, is directly bonded to sp 3 carbon. Vinyl: X is bonded to

More information

Loudon Chapter 19 Review: Aldehydes and Ketones CHEM 3331, Jacquie Richardson, Fall Page 1

Loudon Chapter 19 Review: Aldehydes and Ketones CHEM 3331, Jacquie Richardson, Fall Page 1 Loudon Chapter 19 eview: Aldehydes and Ketones CEM 3331, Jacquie ichardson, Fall 2010 - Page 1 Beginning with this chapter, we re looking at a very important functional group: the carbonyl. We ve seen

More information

Organic Chemistry Review: Topic 10 & Topic 20

Organic Chemistry Review: Topic 10 & Topic 20 Organic Structure Alkanes C C σ bond Mechanism Substitution (Incoming atom or group will displace an existing atom or group in a molecule) Examples Occurs with exposure to ultraviolet light or sunlight,

More information

Nucleophilic Substitution and Elimination

Nucleophilic Substitution and Elimination Nucleophilic Substitution and Elimination Alkyl halides react with a nucleophile in one of two ways. Either they eliminate an X to form an alkene, or they undergo a substitution with the nucleophile, Nu,

More information

Part C- section 1 p-bonds as nucleophiles

Part C- section 1 p-bonds as nucleophiles Part C- section 1 p-bonds as nucleophiles Chemistry of Alkenes (Ch 8, 9, 10) - the double bond prevents free rotation - isomerism cis and trans - nomenclature E and Z (3 or 4 different substituents around

More information

Chem Lecture 23 Page- 1 -

Chem Lecture 23 Page- 1 - Chem 230-001 Lecture 23 Page- 1 - ydroboration/ oxidation - acemic trans-2-methylcyclohexanol may be neatly synthesized from 1-methyl- 1-cyclohexene by using a reagent called borane, 3. 0.33 equivs. 3,

More information

Chapter 8. Substitution reactions of Alkyl Halides

Chapter 8. Substitution reactions of Alkyl Halides Chapter 8. Substitution reactions of Alkyl Halides There are two types of possible reaction in organic compounds in which sp 3 carbon is bonded to an electronegative atom or group (ex, halides) 1. Substitution

More information

Dehydrohalogenation of Alkyl Halides E2 and E1 Reactions in Detail

Dehydrohalogenation of Alkyl Halides E2 and E1 Reactions in Detail Dehydrohalogenation of Alkyl Halides E2 and E1 Reactions in Detail b-elimination Reactions Overview dehydration of alcohols: X = H; Y = OH dehydrohalogenation of alkyl halides: X = H; Y = Br, etc. X C

More information

water methanol dimethyl ether Ether can only act as a hydrogen bond acceptor H-bond acceptor O R

water methanol dimethyl ether Ether can only act as a hydrogen bond acceptor H-bond acceptor O R Chapter 14: Ethers and Epoxides; Thiols and Sulfides 14.1 Introduction to Ethers An ether group is an oxygen atom that is bonded to two carbons. The ether carbons can be part of alkyl, aryl, or vinyl groups.

More information

Ch 18 Ethers and Epoxides

Ch 18 Ethers and Epoxides Ch 18 Ethers and Epoxides Ethers (R-O-R ) are compounds with two organic groups attached to an sp 3 oxygen. Epoxides are cyclic ethers where the sp 3 O is a part of a 3-membered ring. Thiols (R-S-H ) and

More information

HONORS ORGANIC CHEM. HAHS MRS. RICHARDS

HONORS ORGANIC CHEM. HAHS MRS. RICHARDS NRS RGANIC CEM. AS MRS. RICARDS RGANIC CEMISTRY: FINAL EXAM REVIEW List of Topics: While the exam will specifically focus on material from Quarter 2, an understanding of several important concepts from

More information

Reactivity of C=C. Chapter 8 Reactions of Alkenes. Types of Additions. Electrophilic Addition. Addition of HX (1) Addition of HX (2)

Reactivity of C=C. Chapter 8 Reactions of Alkenes. Types of Additions. Electrophilic Addition. Addition of HX (1) Addition of HX (2) rganic hemistry, 5 th Edition L. G. Wade, Jr. hapter 8 Reactions of Alkenes Jo Blackburn Richland ollege, allas, TX allas ounty ommunity ollege istrict 2003, Prentice all Reactivity of = Electrons in pi

More information

Reducing Agents. Linda M. Sweeting 1998

Reducing Agents. Linda M. Sweeting 1998 Reducing Agents Linda M. Sweeting 1998 Reduction is defined in chemistry as loss of oxygen, gain of hydrogen or gain of electrons; the gain of electrons enables you to calculate an oxidation state. Hydride

More information

PAPER No. : Paper-9, Organic Chemistry-III (Reaction Mechanism-2) MODULE No. : Module-10, Hydroboration Reaction CHEMISTRY

PAPER No. : Paper-9, Organic Chemistry-III (Reaction Mechanism-2) MODULE No. : Module-10, Hydroboration Reaction CHEMISTRY Subject Chemistry Paper No and Title Module No and Title Module Tag Paper-9, Organic Chemistry-III (Reaction Mechanism-2) Module-10, Hydroboration Reaction CHE_P9_M10 TABLE OF CONTENTS 1. Learning Outcomes

More information

An unknown molecule A has 4 signals in the 1 H NMR spectrum. Which of the following corresponds to molecule A

An unknown molecule A has 4 signals in the 1 H NMR spectrum. Which of the following corresponds to molecule A An unknown molecule A has 4 signals in the 1 H NMR spectrum. Which of the following corresponds to molecule A How many nonequivalent protons does the following structure have? 4 Reading from left to right,

More information

Organic Reactions Susbstitution S N. Dr. Sapna Gupta

Organic Reactions Susbstitution S N. Dr. Sapna Gupta Organic Reactions Susbstitution S N 2 Dr. Sapna Gupta Kinetics of Nucleophilic Reaction Rate law is order of reaction 0 order is when rate of reaction is unaffected by change in concentration of the reactants

More information

(c) The intermediate carbocation resulting from 3-bromobut-1-ene is resonance stabilized.

(c) The intermediate carbocation resulting from 3-bromobut-1-ene is resonance stabilized. KT121 Sem II 09/10 SETIN B: 1.(a) Name of mechanism: E1 elimination. 7 marks (b) (i) + 3 3 3 (ii) + 3 (iii) l 8 marks (c) The intermediate carbocation resulting from 3-bromobut-1-ene is resonance stabilized.

More information

CEM 351 2nd EXAM/Version A Friday, October 17, :50 2:40 p.m. Room 138, Chemistry

CEM 351 2nd EXAM/Version A Friday, October 17, :50 2:40 p.m. Room 138, Chemistry Name (print) Signature Student # Section Number CEM 351 2nd EXAM/Version A Friday, October 17, 2003 1:50 2:40 p.m. Room 138, Chemistry Ann Swerkey Grade? 1.(20 2.(20. 3.(20 4.(20 5.(20 6.(20 TOTAL 100

More information

NAME: STUDENT NUMBER: Page 1 of 7

NAME: STUDENT NUMBER: Page 1 of 7 NAME: STUDENT NUME: Page 1 of 7 CEM 3390 Midterm Test Monday ctober 26 and Tuesday ctober 27, 2008 This test is graded out of 40 Marks. You must complete all work within TW US. Put all answers in the spaces

More information

Lecture Notes Chem 51C S. King. Chapter 20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation & Reduction

Lecture Notes Chem 51C S. King. Chapter 20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation & Reduction Lecture Notes Chem 51C S. King Chapter 20 Introduction to Carbonyl Chemistry; rganometallic Reagents; xidation & Reduction I. The Reactivity of Carbonyl Compounds The carbonyl group is an extremely important

More information

Chapter 3. Alkenes And Alkynes

Chapter 3. Alkenes And Alkynes Chapter 3 Alkenes And Alkynes Alkenes ydrocarbons containing double bonds C C double bond the functional group center of reactivity Molecular Formula of Alkene Acyclic alkene: C n 2n Cyclic alkene: C n

More information

Chapter 13: Alcohols and Phenols

Chapter 13: Alcohols and Phenols Chapter 13: Alcohols and Phenols [ Chapter 9 Sections: 9.10; Chapter 13 Sections: 13.1-13.3, 13.9-13.10] 1. Nomenclature of Alcohols simple alcohols C3 C3C2 Eddie Sachs 1927-1964 larger alcohols find the

More information

Organic Chemistry. Alkenes

Organic Chemistry. Alkenes Organic Chemistry by Nurlin Abu Samah, Dr. Md. Shaheen & Dr. Nadeem Akhtar Faculty of Industrial Sciences & Technology nurlin@ump.edu.my Chapter Description Aims The students should understand the fundamental

More information

Loudon Chapter 14 Review: Reactions of Alkynes Jacquie Richardson, CU Boulder Last updated 1/16/2018

Loudon Chapter 14 Review: Reactions of Alkynes Jacquie Richardson, CU Boulder Last updated 1/16/2018 An alkyne is any molecule with a triple bond between two carbon atoms. This triple bond consists of one σ bond and two π bonds: the σ bond exists on a straight line between carbon atoms, while one π bond

More information

1. Addition of HBr to alkenes

1. Addition of HBr to alkenes eactions of Alkenes I eading: Wade chapter 8, sections 8-1- 8-8 tudy Problems: 8-47, 8-48, 8-55, 8-66, 8-67, 8-70 Key Concepts and kills: Predict the products of additions to alkenes, including regiochemistry

More information

Chapter 8 Alkyl Halides and Elimination Reactions

Chapter 8 Alkyl Halides and Elimination Reactions Organic Chemistry, Second Edition Janice Gorzynski Smith University of Hawai i Chapter 8 Alkyl Halides and Elimination Reactions Prepared by Rabi Ann Musah State University of New York at Albany Copyright

More information

CHEMISTRY Topic #4: Electrophilic Addition Reactions of Alkenes and Alkynes Fall 2018 Dr. Susan Findlay

CHEMISTRY Topic #4: Electrophilic Addition Reactions of Alkenes and Alkynes Fall 2018 Dr. Susan Findlay EMISTRY 2600 Topic #4: Electrophilic Addition Reactions of Alkenes and Alkynes Fall 2018 Dr. Susan Findlay rganic Reactions (EM 2500 Review) Most reactions in organic chemistry fall into one (or more)

More information

Problem Set 8: Substitution Reactions-ANSWER KEY. (b) nucleophile NH 3 H C. (d) H 3 N

Problem Set 8: Substitution Reactions-ANSWER KEY. (b) nucleophile NH 3 H C. (d) H 3 N Problem Set 8: Substitution Reactions-ANSWER KEY hemistry 260 rganic hemistry 1. The answers are (1), (3) and (5). Nucleophiles generally have lone pair and/or negative charge. 2. (a) neither 4 (c) nucleophile

More information

3-chloro-1-propene 1-chloropropane 2-chloropropene

3-chloro-1-propene 1-chloropropane 2-chloropropene ANSWERS #1. (from 50 minute exam #3, Fall 2000) 5. (6 points) For each group of 3 compounds, identify the compound that expresses the indicated property the MOST and the compound that expresses it the

More information

What are radicals? H. Cl. Chapter 10 Radical Reactions. Production of radicals. Reactions of radicals. Electronic structure of methyl radical

What are radicals? H. Cl. Chapter 10 Radical Reactions. Production of radicals. Reactions of radicals. Electronic structure of methyl radical What are radicals? Radicals are intermediates with an unpaired electron Chapter 10 Radical Reactions H. Cl. Hydrogen radical Chlorine radical Methyl radical Often called free radicals Formed by homolytic

More information

CHEMISTRY 231 GENERAL ORGANIC CHEMISTRY I FALL 2014 List of Topics / Examination Schedule

CHEMISTRY 231 GENERAL ORGANIC CHEMISTRY I FALL 2014 List of Topics / Examination Schedule Page 1 of 5 CHEMISTRY 231 FALL 2014 List of Topics / Examination Schedule Unit Starts Topic of Study 20 Aug 2014 STRUCTURE AND BONDING Suggested Reading: Chapter 1 29 Aug 2014 ALKANES & CYCLOALKANES Suggested

More information

c. Cl H Page 1 of 7 major P (E > Z and more substituted over less substituted alkene) LG must be axial are the same Cl -

c. Cl H Page 1 of 7 major P (E > Z and more substituted over less substituted alkene) LG must be axial are the same Cl - CEM 109A 1. Predict the products of the following reactions (a-c E2, d-f E1 KEY focuses only on elimination products, in most cases there will also be substitution products.) a. - LG must be axial - are

More information