Chapter 7: Alkenes and Alkynes
|
|
|
- Vanessa Casey
- 6 years ago
- Views:
Transcription
1 Chapter 7: Alkenes and Alkynes ydrocarbons Containing Double and Triple Bonds Unsaturated Compounds (Less than Maximum Atoms) Alkenes also Referred to as Olefins Properties Similar to those of Corresponding Alkanes Slightly Soluble in Water Dissolve Readily in Nonpolar or Low Polarity Solvents Densities of Alkenes and Alkynes Less than Water
2 Isomerism: Cis/Trans Cl C C Cl Cl C Cl C Cis or (Z) Trans or (E) Same Molecular Formula (C 2 Cl 2 2 ) and Connectivity Different Structures Double Bonds Don t Rotate For Tri/Tetra Substituted Alkenes; Use (E), (Z) Labels
3 Alkenes: Relative Stability > > > Tetrasubstituted Trisubstituted Geminal Disubstituted Trans Disubstituted > > Cis Disubstituted Monosubstituted Unsubstituted igher Alkyl Substitution = igher Alkene Stability Note Stability Trends of Disubstituted Alkenes Can Also Observe Cyclic Alkenes
4 Alkenes: Cyclic Structures C 2 C C C 2 C 2 C C 2 2 C C C 2 C C Cyclopropene Cyclobutene Cyclopentene C 2 C C 2 C C C C C 2 C 2 Cyclohexene Note all of These are Cis Alkenes Can Observe Trans Cycloalkenes; z.b. trans-cycloctene trans-cycloheptene Observable Spectroscopically; Can t Isolate C C C Cyclohexatriene (Benzene)
5 Alkenes: Synthesis via Elimination C 2 5 ONa Br O Br Dehydrohalogenation; E 2 Elimination Reaction E 2 Reactions Preferable Over E 1 (Rearrangement; SN 1 Products) Usually eat These Reactions (eat Favors Elimination)
6 Alkenes: Zaitsev s Rule C 2 C 3 C 2 5 ONa 3 C Br 3 C 31% C 3 3 C C 3 C 3 C 3 C 2 5 ONa Br 3 C 69% C 3 If Multiple Possible Products; Most Stable (Substituted) Forms More Substituted: Product and Transition State Lower in Energy
7 Alkenes: Forming the Least Substituted C 2 C 3 OK 3 C Br 3 C 72.5% C 3 C 3 C 3 OK C3 3 C Br 3 C Bulky Base Favors Least Substituted Product 27.5% C 3 Due to Steric Crowding in Transition State (2 ydrogens)
8 Alkenes: The Transition State in E 2 O Orientation Allows Proper Orbital Overlap in New π Bond Syn Coplanar Transition State only in Certain Rigid Systems Anti: Staggered; Syn: Eclipsed Anti TS is Favored Br Anti Coplanar Conformation (ydrogen and Leaving Group)
9 Alkenes: E 2 Reactions of Cyclohexanes EtO Cl Anti Transition State Attainable w/ Axial and Leaving Group Axial/Equatorial and Equatorial/Equatorial Improper Combos Let s Look at igher Substituted Cyclohexanes
10 Alkenes: E 2 Reactions of Cyclohexanes EtO EtO Me Me i Pr + Cl i Pr i Pr Multiple s Axial to Leaving Group Multiple Products Zaitsev s Rule Governs Product Formation 22% 78% (Zaitsev's Rule) What if NO Anti Coplanar Arrangement in Stable Conformer??
11 Alkenes: E 2 Reactions of Cyclohexanes Me i Pr Cl Me Cl Me i Pr i Pr EtO All Groups Equatorial in Most Stable Conformation 100% Chair Flip Form has Proper Alignment Reaction Proceeds Through igh Energy Conformation Only ONE Possible Elimination Product In This Case
12 Alkenes: Acid Catalyzed Dehydration O concd 2SO o C + 2 O O 85% 3 PO o C + 2 O ave to Pound 1 Alcohols to Dehydrate w/ Acid 2 Alcohols Easier, Can Use Milder Conditions
13 Alkenes: Acid Catalyzed Dehydration C 3 C 2 3 C C 2 O 20% 2 SO 4 85 o C 3 C C O 3 Alcohols Exceptionally Easy to Dehydrate Can Use Dilute Acid, Lower Temperatures Relative Ease of Reaction: 3 > 2 > 1
14 Alkenes: Acid Catalyzed Dehydration C 3 C 3 3 C O + 3 C O 2 C 2 C 2-2 O 3 C C 2 C O - + Base C 2 C 3 E 1 Elimination Reaction Mechanism (Explains Ease) C 3
15 Alkenes: Acid Catalyzed Dehydration 3 Alcohols Easiest to Dehydrate via E 1 ; 1 ardest Recall Carbocation Stablility: 3 > 2 > 1 Relative Transition State Stability Related to Carbocation Why Are More Substituted Carbocations More Stable?? YPERCONJUGATION (Donating Power of Alkyls) 1 Carbocation Instablility Dehydration of These is E 2
16 Alkenes: 1 Alcohol Dehydration (E 2 ) C 3 C 3 3 C O A 3 C O 2 A Step One Fast Step Two Slow (RDS) 3 C + 2 O + -A 3 C Proceeds via E 2 Due to Primary Carbocation Instability Sulfuric and Phosphoric Acids Are Commonly Used Acids
17 Carbocation Rearrangements 3 C C 3 C 3 85% 3 PO 4 eat 3 C C 3 + C 3 C 3 O 3 C C 3 C(C 3 ) 2 Major Minor C 3 C 3 3 C C 3 3 C C 3 C 3 O 2 C 3 A Priori One Expects the Minor Dehydration Product This Dehydration Product is NOT Observed Major Product
18 Carbocation Rearrangements (2) C 3 C 3 Methanide 3 C C 3 3 C Migration C 3 C 3 C 3 Secondary Carbocation C 3 Tertiary Carbocation 3 C C 3 Methanide Migration Results in More Stable 3 Carbocation This Carbocation Gives Rise to Observed Major Product Can Also Observe YDRIDE ( - ) Shifts More Stable C + C Transition State
19 Alkyne Synthesis: Dehydrohalogenation 2 eq. NaN 2 R R R R Br Br Compounds w/ alogens on Adjacent Carbons: VICINAL Dihalides (Above Cmpd: Vicinal Dibromide) Entails Consecutive E 2 Elimination Reactions NaN 2 Strong Enough to Effect Both Eliminations in 1 Pot Need 3 Equivalents NaN 2 for Terminal Alkynes
20 Reactions: Alkylation of Terminal Alkynes 3 C NaN 2 N 3 3 C C 3 Br 3 C C 3 3 C NaN 2 N 3 3 C EtBr 3 C Et NaN 2 ( - N 2 ) to Deprotonate Alkyne (Acid/Base Reaction) Anion Reacts with Alkyl alide (Bromide); Displaces alide Alkyl Group Added to Alkyne Alkyl alide Must be 1 or Me; No Branching at 2 nd (β) Carbon
21 Reactions: Alkylation of Terminal Alkynes SN 2 Substitution Reactions on 1 alides E 2 Eliminations Occur on Reactions w/ 2, 3 alides Steric Problem; Proton More Accessible than Electrophilic Carbon Atom 3 C C 3 C C Br 3 C 3 C + 3 C C 3
22 Alkenes: ydrogenation Reactions 2 Pt, Pd, or Ni (catalyst) Solvent, Pressure Alkene Alkane Catalytic ydrogenation is a SYN Addition of 2 SYN Addition: Both Atoms Add to Same Side (Face) of π Bond Catalyst: Lowers Transition State Energy (Activation Energy)
23 Alkynes: ydrogenation Reactions Alkyne 2 2 Pt (catalyst) Solvent, Pressure Alkane Platinum Catalysts Allow Double Addition of 2 On Alkyne Can Also ydrogenate Once to Generate Alkenes Cis and Trans (E and Z) Stereoisomers are Possible Can Control Stereochemistry with Catalyst Selection
24 Alkynes: ydrogenation to Alkenes 2 /Ni 2 B 97% R R R R 2, Pd/CaCO 3 Quinoline SYN Additions to Alkynes (Result in cis/z Alkenes) Reaction Takes Place on Surface of Catalyst Examples of a ETEROGENEOUS Catalyst System
25 Alkynes: ydrogenation to Alkenes (1) Li, C 2 5 N 2 (2) N 4 Cl Dissolving Metal Reduction Reaction ANTI Addition of 2 to Alkyne E (trans) Stereoisomer Ethylamine or Ammonia can be used for Reaction
26 More On Unsaturation Numbers Unsaturation Number (r + π) Index of Rings and Multiple Bonds r + π = C - ½ + ½ N - ½ alogen + 1 Useful When Generating Structures from Molecular Formula Also Called Degree of ydrogen Deficiency; Number of Double Bond Equivalencies Often Combined with Spectroscopic Data when Making Unknown Structure Determinations
27 Chapter 7: Key Concepts E2 Eliminations w/ Large and Small Bases E1 Elimination Reactions Zaitsev s Rule Carbocation Rearrangement Dehydration and Dehydrohalogenation Reactions Synthesis of Alkynes ydrogenation Reactions (Alkynes to E/Z Alkenes) Unsaturation Numbers; Utility in Structure Determination
Chapter 7 Alkenes and Alkynes I: Properties and Synthesis Elimination Reactions of Alkyl Halides"
Chapter 7 Alkenes and Alkynes I: Properties and Synthesis Elimination Reactions of Alkyl Halides The (E)-(Z) System for Designating Alkene Diastereomers The Cahn-Ingold-Prelog convention is used to assign
Chapter 7 - Alkenes and Alkynes I
Andrew Rosen Chapter 7 - Alkenes and Alkynes I 7.1 - Introduction - The simplest member of the alkenes has the common name of ethylene while the simplest member of the alkyne family has the common name
Structure and Preparation of Alkenes: Elimination Reactions
Structure and Preparation of Alkenes: Elimination Reactions Alkene Nomenclature First identify the longest continuous chain that includes the double bond. Replace the -ane ending of the corresponding unbranched
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
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
ORGANIC CHEMISTRY. Chapter Cycloalkenes. Department of Chemistry, Xiamen University
ORGANI EMISTRY hapter 7 7.4 ycloalkenes Department of hemistry, Xiamen University ORGANI EMISTRY hapter 7 The rings of cycloalkenes containing five carbon atoms or fewer exist only in the cis form. yclopropene
Name the following compounds (include stereochemistry, cis/trans, E/Z when appropriate). Cl E- 6 chloro, 5 ethyl, 4 methyl 3-octene
Problem Set 6 Name the following compounds (include stereochemistry, cis/trans, E/Z when appropriate). E- 6 chlo, 5 ethyl, 4 methyl 3-octene 5 methyl, 3 vinyl cyclohexene 7Z- 7 bromo 4 ethyl, 6 methyl
ORGANIC CHEMISTRY- 1
ORGANIC CEMISTRY- 1 ALKENES Alkenes are also called Olefins (C n 2n ) unsaturated hydrocarbons. Alkenes occur abundantly in nature. Ethylene ( 2 C=C 2 ) is a plant hormone that induces ripening in fruit.
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
Chapter 7 Alkenes; Elimination Reactions
hapter 7 Alkenes; Elimination Reactions Alkenes Alkenes contain a carbon-carbon double bond. They are named as derivatives of alkanes with the suffix -ane changed to -ene. The parent alkane is the longest
Chapter 9 Alkynes. Introduction
hapter 9 Alkynes Introduction Alkynes contain a triple bond. General formula is n 2n-2. Two elements of unsaturation for each triple bond. MST reactions are like alkenes: addition and oxidation. Some reactions
Alkenes. Dr. Munther A. M-Ali For 1 st Stage Setudents
Alkenes Dr. Munther A. M-Ali For 1 st Stage Setudents Alkenes Family of hydrocarbons, the alkenes, which contain less hydrogen, carbon for carbon, than the alkanes Structure of ethylene, The carbon-carbon
Chapter 8: Chemistry of Alkynes (C n H 2n-2 )
hapter 8: hemistry of Alkynes ( n 2n-2 ) Bonding & hybridization Both are sp-hybridized Bond angles = 180 o 1 σ + 2 π bonds Linear around lassification R R R' σ bond energy: 88 kcal/mol π bond energy:
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
CHEM 261 HOME WORK Lecture Topics: MODULE 1: The Basics: Bonding and Molecular Structure Text Sections (N0 1.9, 9-11) Homework: Chapter 1:
CHEM 261 HOME WORK Lecture Topics: MODULE 1: The Basics: Bonding and Molecular Structure Atomic Structure - Valence Electrons Chemical Bonds: The Octet Rule - Ionic bond - Covalent bond How to write Lewis
1. Introduction. Cis-Trans System Useful for 1,2-disubstituted alkenes Examples: Alkynes Hydrocarbons containing C C Common name: acetylenes
hapter 7 Alkenes and Alkynes I: Properties and Synthesis. Elimination eactions of Alkyl alides reated by Professor William Tam & Dr. illis hang h. 7-1 About The Authors These PowerPoint Lecture Slides
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
Organic Chemistry I Lesson Objectives, Lesson Problems, Course Outline Spring 2008
Organic Chemistry I Lesson Objectives, Lesson Problems, Course Outline Spring 2008 Lesson Date Assignment Lesson Objective Description Lesson Problems 4 14-Jan Chapter 1 Quiz Describe how bond polarity
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)
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
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
Lecture 20 Organic Chemistry 1
CEM 232 rganic Chemistry I at Chicago Lecture 20 rganic Chemistry 1 Professor Duncan Wardrop March 18, 2010 1 Self-Test Question Capnellene (4) is a marine natural product that was isolated from coral
Detailed Course Content
Detailed Course Content Chapter 1: Carbon Compounds and Chemical Bonds The Structural Theory of Organic Chemistry 4 Chemical Bonds: The Octet Rule 6 Lewis Structures 8 Formal Charge 11 Resonance 14 Quantum
Alkenes. Alkenes-hydrocarbons with a carbon-carbon double bond. Alkenes have the formula C n H 2n. Nomenclature
Alkenes Alkenes-hydrocarbons with a carbon-carbon double bond. Alkenes have the formula n 2n. Nomenclature Alkenes are named in the same manner as alkanes with the following adjustments. 1. Find the longest
Lecture 11 Organic Chemistry 1
EM 232 rganic hemistry I at hicago Lecture 11 rganic hemistry 1 Professor Duncan Wardrop February 16, 2010 1 Self Test Question What is the product(s) of the following reaction? 3 K( 3 ) 3 A 3 ( 3 ) 3
Chapter 7: Alkene reactions conversion to new functional groups
hapter 7: Alkene reactions conversion to new functional groups Preparation of alkenes: two common elimination reactions 1. Dehydration of alcohols Dehydration is a common biochemical reaction in carbohydrate
Chapter 8: Addition Reactions
Chapter 8: Addition Reactions Addition Reactions to Alkenes (Section 8.1) Markovnikov s Rule (Section 8.2) Stereochemistry of Ionic Addition to Alkenes (Section 8.3) 2 S 4 Additions to Alkenes (Section
CHAPTER 3 ALKENES, ALKYNES & CONJUGATE DIENES
CHEM 244 PRINCIPLES OF ORGANIC CHEMISTRY I FOR CHEMICAL ENGINEERING STUDENTS, COLLEGE OF ENGINEERING PRE-REQUISITES COURSE; CHEM 101 CREDIT HOURS; 2 (2+0) Dr. Mohamed El-Newehy Chemistry Department, College
The Electrophile. S N 2 and E2 least stable most stable least hindered most hindered. S N 1 and E1. > x > >
The Electrophile 1 Recall that electrophile means electron- loving. When considering substitution and elimination reactions we must consider the carbon attached to the leaving group. Is it a primary, secondary,
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
Chapter 7: Alkenes: Reactions and Synthesis
hapter 7: Alkenes: Reactions and Synthesis alcohol alkane halohydrin 1,2-diol 1,2-dihalide carbonyl halide halide Addition Y Y Elimination Electrophilic Addition Dehydrohalogenation: loss of from an alkyl
Classes of Alkenes. Alkenes and Alkynes. Saturated compounds (alkanes): Have the maximum number of hydrogen atoms attached to each carbon atom.
Alkenes and Alkynes Saturated compounds (alkanes): ave the maximum number of hydrogen atoms attached to each carbon atom. Unsaturated compounds: ave fewer hydrogen atoms attached to the carbon chain than
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
Organic Chemistry I: Reactions and Overview
Organic Chemistry I: Reactions and Overview Andrew Rosen Editor: Raghav Malik January 13, 2013 Contents I Library of Synthetic Reactions 3 II Organic Trends and Essentials 4 1 The Basics: Bonding and Molecular
sp 2 geometry tetrahedral trigonal planar linear ΔH C-C ΔH C-H % s character pk a 464 KJ/mol 33% 44
hapter 10: Alkynes 10.1 Introduction to Alkynes ~ 111 ~ 122 1.06 Å 180 1.1 Å ~ 116 1.08 Å 1.54 Å 1.34 Å 1.20 Å hybridization of sp 3 sp 2 sp geometry tetrahedral trigonal planar linear 368 KJ/mol 632 KJ/mol
Organic Chemistry The Functional Group Approach. Organic Chemistry The Functional Group Approach
Organic Chemistry The Functional Group Approach OH Br alkane (no F.G.) alcohol halide alkene non-polar (grease, fats) O NH alkyne aromatic aldehyde/ketone imine linear flat Organic Chemistry The Functional
台灣大學開放式課程 有機化學乙 蔡蘊明教授 本著作除另有註明, 作者皆為蔡蘊明教授, 所有內容皆採用創用 CC 姓名標示 - 非商業使用 - 相同方式分享 3.0 台灣授權條款釋出
台灣大學開放式課程 有機化學乙 蔡蘊明教授 本著作除另有註明, 作者皆為蔡蘊明教授, 所有內容皆採用創用 姓名標示 - 非商業使用 - 相同方式分享 3.0 台灣授權條款釋出 hapter 7 Alkenes and alkynes: synthesis alkenes also called olefins alkynes common name: acetylenes Nomenclature
C h a p t e r S e v e n : Haloalkanes: Nucleophilc Substitution and Elimination Reactions S N 2
C h a p t e r S e v e n : Haloalkanes: Nucleophilc Substitution and Elimination Reactions S N 2 CHM 321: Summary of Important Concepts Concepts for Chapter 7: Substitution Reactions I. Nomenclature of
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
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
ORGANIC - EGE 5E CH. 7 - NUCLEOPHILIC SUBSTITUTION AND ELIMINATION REACTIONS
!! www.clutchprep.com CONCEPT: INTRODUCTION TO SUBSTITUTION Previously, we discussed the various ways that acids could react with bases: Recall that in these mechanisms, electrons always travel from density
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,
Alkyl Halides. Alkyl halides are a class of compounds where a halogen atom or atoms are bound to an sp 3 orbital of an alkyl group.
Alkyl Halides Alkyl halides are a class of compounds where a halogen atom or atoms are bound to an sp 3 orbital of an alkyl group. CHCl 3 (Chloroform: organic solvent) CF 2 Cl 2 (Freon-12: refrigerant
Lecture Notes Chem 51B S. King I. Conjugation
Lecture Notes Chem 51B S. King Chapter 16 Conjugation, Resonance, and Dienes I. Conjugation Conjugation occurs whenever p-orbitals can overlap on three or more adjacent atoms. Conjugated systems are more
CHE1502. Tutorial letter 201/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry CHE1502/201/1/2016
CE1502/201/1/2016 Tutorial letter 201/1/2016 General Chemistry 1B CE1502 Semester 1 Department of Chemistry This tutorial letter contains the answers to the questions in assignment 1. FIRST SEMESTER: KEY
1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound?
CEM 331: Chapter 1/2: Structures (Atoms, Molecules, Bonding) 1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound? N C 2 C N C 2 C N 1 2 3 4 1: three sigma bonds and
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320 I. Isolated, cumulated, and conjugated dienes A diene is any compound with two or C=C's is a diene. Compounds containing more than two
REVIEW PROBLEMS Key. 1. Draw a complete orbital picture for the molecule shown below. Is this molecule chiral? Explain. H H.
rganic hemistry II (E325) REVIEW PRBLEMS Key 1. Draw a complete orbital picture for the molecule shown below. Is this molecule chiral? Explain. 3 3 sp3 orbital p orbital sp2 orbital s orbital molecule
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
7ALKENES AND ALKYNES I:
7ALKENES AND ALKYNES I: PROPERTIES AND SYNTESIS. ELIMINATION REATIONS OF ALKYL ALIDES SOLUTIONS TO PROBLEMS 7.1 (a) (E )-1-omo-1-chlo-1-pentene (E )-1-omo-1-chlopent-1-ene (E )-2-omo-1-chlo-1-iodo-1-butene
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
Chapter 8 Addition Reactions to Alkenes
. 8 hapter 8 Addition eactions to Alkenes In this chapter will we study the addition reactions of alkenes. We will see that the π electrons of the double bond are loosely held and that their maximum electron
(1) Recall the classification system for substituted alkenes. (2) Look at the alkene indicated. Count the number of bonds to non-hydrogen groups.
Organic Chemistry - Problem Drill 10: Alkenes, Alkynes, and Dienes No. 1 of 10 1. What is the substitution pattern for alkene indicated below? (A) mono (B) di (C) tri (D) tetra (E) unsubstituted Mono is
ALKANES STRUCTURE, PROPERTIES, AND SYNTHESIS A STUDENT WHO HAS MASTERED THE MATERIAL IN THIS SECTION SHOULD BE ABLE TO:
ALKANES STRUCTURE, PROPERTIES, AND SYNTESIS A STUDENT WO AS MASTERED TE MATERIAL IN TIS SECTION SOULD BE ABLE TO: 1. Predict relative boiling points of alkanes, in comparison with other alkanes and with
nsaturated Hydrocarbons: Alkenes, Cycloalkenes and Dienes
240 Chem nsaturated Hydrocarbons: Alkenes, Cycloalkenes and Dienes 1 Chapter 3 Alkenes or Olefines Crabon-Carbon double bond C n H 2n Hybridization in Alkenes: 1.34 A 2 Nomenclature of Alkenes and Cycloalkenes
CONCERTED sp 2 H. HO Et
Alkyl alides Substitution and Elimination 1 Substitutions (Quick Review) 1.1 SN2 Reactions LB nucleophile "backside attack!" NERTED reaction This is fundamentally just a Lewis acid/base reaction, the Lewis
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
Conjugated Systems, Orbital Symmetry and UV Spectroscopy
Conjugated Systems, Orbital Symmetry and UV Spectroscopy Introduction There are several possible arrangements for a molecule which contains two double bonds (diene): Isolated: (two or more single bonds
Chapter 9 Alkynes. Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Chapter 9 Alkynes Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display. 9.1 Sources of Alkynes Acetylene Industrial preparation of acetylene is by dehydrogenation of
Learning Guide for Chapter 13 - Alkynes
Learning Guide for Chapter 13 - Alkynes I. Introduction to Alkynes - p 1 II. Natural ccurrence and Uses of Alkynes - p 5 III. Physical Properties of Alkynes - p 7 IV. Spectroscopy of Alkynes - p 7 V. Nomenclature
Chem 251 Fall Learning Objectives
Learning Objectives Chapter 8 (last semester) 1. Write an electron-pushing mechanism for an SN2 reaction between an alkyl halide and a nucleophile. 2. Describe the rate law and relative rate of reaction
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
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.
Learning Guide for Chapter 11 - Alkenes I
Learning Guide for Chapter 11 - Alkenes I I. Introduction to alkenes - p 1 bond structure, classifying alkenes, reactivity, physical properties, occurrences and uses, spectroscopy, stabilty II. Unsaturation
Introduction & Definitions Catalytic Hydrogenations Dissolving Metal Reduction Reduction by Addition of H- and H+ Oxidation of Alcohols Oxidation of
CEM 241- UNIT 4 xidation/reduction Reactions Redox chemistry 1 utline Introduction & Definitions Catalytic ydrogenations Dissolving Metal Reduction Reduction by Addition of - and + xidation of Alcohols
ORGANIC - EGE 5E CH. 5 - ALKANES AND CYCLOALKANES.
!! www.clutchprep.com CONCEPT: ALKANE NOMENCLATURE Before 1919, chemists literally had to memorize thousands of random (common) chemical names. IUPAC naming provides a systematic method to give every chemical
Organometallic Chemistry and Homogeneous Catalysis
rganometallic hemistry and omogeneous atalysis Dr. Alexey Zazybin Lecture N8 Kashiwa ampus, December 11, 2009 Types of reactions in the coordination sphere of T 3. Reductive elimination X-L n -Y L n +
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
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
CHAPTER 8 HW SOLUTIONS: ELIMINATIONS REACTIONS
APTER 8 W SLUTNS: ELMNATNS REATNS S-TRANS SMERSM 1. Use a discussion and drawing of orbitals to help explain why it is generally easy to rotate around single bonds at room temperature, while it is difficult
Chapter 5. Reactions of Alkenes and Alkynes
Chapter 5. Reactions of Alkenes and Alkynes Learning objectives: 1. Identify the followings from a reaction coordinate diagram when applicable: endothermic or exothermic reactions, activation energy, heat
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
OCH 3. 3-butyn-2-ol 3-hydroxy-1-butyne
Alkynes, Part I eading: Wade chapter 9, sections 9-1- 9-8 Study Problems: 9-29, 9-32, 9-36 Key oncepts and Skills: Explain why alkynes are more acidic than alkanes or alkenes; show how to generate nucleophilic
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES.
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following: See Test1-4 Objectives/Competencies as listed in the syllabus and on the main course
Nucleophilic Substitution & Elimination Chemistry 1
ucleophilic Substitution & Elimination hemistry 1 What kind of mechanisms are possible? What is the major mechanism occuring? Write in ALL mechanism details (lone pairs, formal charge, curved arrows, etc.).
Organic Chemistry. Alkynes
For updated version, please click on http://ocw.ump.edu.my Organic Chemistry Alkynes by Dr. Seema Zareen & Dr. Izan Izwan Misnon Faculty Industrial Science & Technology seema@ump.edu.my & iezwan@ump.edu.my
C h a p t e r E i g h t: Alkenes: Structure and Preparation via Elimination Reactions. 5-Androstene, the parent alkene for most anabolic steroids
C h a p t e r E i g h t: Alkenes: Structure and Preparation via Elimination Reactions 5-Androstene, the parent alkene for most anabolic steroids CHM 321: Summary of Important Concepts YConcepts for Chapter
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
11/5/ Conjugated Dienes. Conjugated Dienes. Conjugated Dienes. Heats of Hydrogenation
8.12 Sites of unsaturation Many compounds have numerous sites of unsaturation If sites are well separated in molecule they react independently If sites are close together they may interact with one another
Homework Problem Set 9 Iverson CH320M/328M Due Friday, November 30
omework Problem Set 9 Iverson C0M/8M Due Friday, November 0 NAME (Print): SIGNATURE: Chemistry 0M/8M Dr. ent Iverson 9th omework November 9, 08 Please print the first three letters of your last name in
1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound?
EM 331: hapter 1/2: Structures (Atoms, Molecules, Bonding) 1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound? N 2 N 2 N 1 2 3 4 2. What hybrid orbitals are used to
STRUCTURE. Dr. Sheppard CHEM 2411 Spring 2015
STRUCTURE Dr. Sheppard CHEM 2411 Spring 2015 Klein (2nd ed.) sections 1.8-1.10, 1.12-1.13, 2.7-2.12, 3.2, 3.4-3.5, 3.8-3.9, 4.6-4.13, 4.14, 8.5, 15.16, 21.3 Topics Structure Physical Properties Hybridization
ORGANIC - BROWN 8E CH ALKENES AND REACTIONS OF ALKENES
!! www.clutchprep.com CONCEPT: ALKENES and ALKYNES Alkenes/Alkynes are named by adding the suffix modifier (- /- ) to the end of the root. Alkenes/alkynes receive in numbering alkanes Location is assigned
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
Chemistry 110. Bettelheim, Brown, Campbell & Farrell. Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes.
Chemistry 110 Bettelheim, Brown, Campbell & Farrell Ninth Edition Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes Chapter 12 Alkenes are hydrocarbons which have one or more
Chemistry 110 Bettelheim, Brown, Campbell & Farrell Ninth Edition Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes
Chemistry 110 Bettelheim, Brown, Campbell & Farrell Ninth Edition Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes Chapter 12 Alkenes are hydrocarbons which have one or more
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
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
16.1 Draw Newman projections for these staggered and three eclipsed conformations of 1, 2 - dichlorobutane as viewed downt he central C-C bond.
CAPTER 16 Practice Exercises 16.1 Draw Newman projections for these staggered and three eclipsed conformations of 1, 2 - dichlorobutane as viewed downt he central C-C bond. 16.3 (a) The more stable conformation
N.b. A catalyst is a species which speeds up a chemical reaction but which remains chemically unchanged. Reverse process of dehydration of an alcohol
An Introduction to Organic hemistry N.b. A catalyst is a species which speeds up a chemical reaction but which remains chemically unchanged. ydration (Addition) Reverse process of dehydration of an alcohol
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
OChem1 Old Exams. Chemistry 3719 Practice Exams
OChem1 Old Exams Chemistry 3719 Practice Exams Fall 2017 Chemistry 3719 Practice Exam A1 This exam is worth 100 points out of a total of 600 points for Chemistry 3719/3719L. You have 50 minutes to complete
Chapter 6 H 2 H 3 C C H CH 3 C H H 2 C C CH 3. (b) =2 H 2 C C C H H C H CH 2 C CH 3 H 3 C C C CH 3. (c) =2
hapter 6 6.1 alculate the degree of the unsaturation in the following hydrocarbons: 8 14 ; 5 6 (c) 12 20 (d) 20 32 (e) 40 56 =2 =3 (c) =3 (d) =5 (e) =13 6.2 alculate the degree of the unsaturation in the
5.5 Physical Properties of Alkenes
5.5 Physical Properties of Alkenes Dipole moments What is direction of dipole moment? Does a methyl group donate electrons to the double bond, or does it withdraw them? µ = 0 D 3 µ = 0.3 D µ = 1.4 D Dipole
Name: Student Number: University of Manitoba - Department of Chemistry CHEM Introductory Organic Chemistry II - Term Test 1
Name: Student Number: University of Manitoba - Department of Chemistry CEM 2220 - Introductory Organic Chemistry II - Term Test 1 Thursday, February 16, 2012; 7-9 PM This is a 2-hour test, marked out of
Chapter 2: An Introduction to Organic Compounds
Chapter : An Introduction to Organic Compounds I. FUNCTIONAL GROUPS: Functional groups with similar structure/reactivity may be "grouped" together. A. Functional Groups With Carbon-Carbon Multiple Bonds.
CHEM 302 Organic Chemistry I Problem Set VII Chapter 7 Answers
CEM 302 rganic Chemistry Problem Set V Chapter 7 Answers 1) The pk a values of acetic acid and trifluroacetic acid are 4.5 and 0.9 respectively. Based on this information, which anion, C 3 C - or CF 3
an axial "X" is necessary for a succesful E2 reaction and also works better for S N 2
cleophilic Substitution & Elimination hemistry 1 Templates for predicting S2 and E2 reactions primary - β α α β two different perspectives secondary - β β α β β α two different perspectives tertiary -
Exam Analysis: Organic Chemistry, Midterm 1
Exam Analysis: Organic Chemistry, Midterm 1 1) TEST BREAK DOWN: There are three independent topics covered in the first midterm, which are hybridization, structure and isomerism, and resonance. The test
ORGANIC - BRUICE 8E CH.3 - AN INTRODUCTION TO ORGANIC COMPOUNDS
!! www.clutchprep.com CONCEPT: INDEX OF HYDROGEN DEFICIENCY (STRUCTURAL) A saturated molecule is any molecule that has the maximum number of hydrogens possible for its chemical structure. The rule that