Mechanical Approach to Drawing 2D, 3D and Resonance Structures from a condensed line formula.
|
|
|
- Philip Lane
- 6 years ago
- Views:
Transcription
1 2D structure drawing hem 314 Beauchamp Mechanical Approach to Drawing 2D, 3D and esonance tructures from a condensed line formula. 1. Draw a 2D structure based on given arrangement shown in condensed line formula 2. ount all valence electrons (make up bonds, lone pairs and radical centers) 3. ount electron in sigma bonds generated (connections = skeleton) and compare to total valence electrons 4. If there are excess electrons, add them in as lone pairs to fill valencies of most electronegative atoms first (F>>). 5. If there are still excess electrons place them at alternate carbon positions to spread out electron density and minimize electron/electron repulsion. If there are still excess electrons left add them to carbon atoms with the fewest sigma bonds. 6. If any atoms lack a full octet, look for adjacent lone pair electrons that can be shared. These will make pi bonds. If there is more than one way to do this, there will be structures. Draw as many of these as are obvious. 7. Evaluate formal charge on all of the atoms. 8. Evaluate structures for relative contributions according to the following rules a. More bonds and full octets is most important = best. b. aving charge consistent with relative electronegativities is second best. 9. Write any additional structures using typical patterns of donor and acceptor sites a. alkene, alkyne and pi bonds are connector components and can donate or accept electrons b. donor sites are atoms with lone pairs of electrons (and pi bonds from a ) c. acceptor sites are neutral polar pi bonds and cationic pi bonds (and pi bonds from a ) 10. To decide each atom s 3D shape, hybridization and bond angles a. Use a structure where an atom has its maximum number of bonds (shows necessary 2p orbitals to make any pi bonds (no pi bonds = sp3, one pi bond = sp2, two pi bonds = sp) b. carbocation carbon atoms use an empty 2p orbital in our course. y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
2 2D structure drawing hem 314 Beauchamp 1. Donor = lone pair next to empty 2p orbital acceptors (usually on carbon as a carbocation) X X X X sp or sp 2 hybridization is possible on either X or F F 2 Many other examples are possible Donor = lone pair next to a pi bond acceptors (polar pi bonds are better acceptors than nonpolar pi bonds) X X X X sp or sp 2 hybridization is possible on either X or Interesting Variations F 2 3. Donor pi bonds (usually alkene, alkyne or ) next to empty 2p orbital acceptors (usually on carbon as a carbocation) X 3. Donor pi bonds (usually alkene, alkyne or ) next to a polar or cationic pi bond acceptors (polar pi bonds are best =, =, =, =, nitrile, but alkene, alkyne and are possible) alkene or alkene or alkene or alkene or Just a few examples. Many more variations. y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
3 2D structure drawing hem 314 Beauchamp use zig-zag drawing for sp 3 chains 1 o carbocation 1 o carbanion 1 o free radical o carbocation 2 o carbanion 2 o free radical alcohol use zig-zag drawing for sp 3 chains protonated alcohol alkoxide ether use zig-zag drawing for sp 3 chains protonated ether carbanion free radical y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
4 2D structure drawing hem 314 Beauchamp o amine use zig-zag drawing for sp 3 chains dialkylammonium ion 2 o amide anion monosubstituted alkene 1 o allylic carbocation 1 o allylic carbanion 1 o allylic free radical imine 1 o allylic carbanion 1 o allylic free radical y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
5 2D structure drawing hem 314 Beauchamp y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc imine 1 o allylic carbanion aldehyde enolate anion protonated carbonyl
6 2D structure drawing hem 314 Beauchamp ketone protonated carbonyl enolate anion alkyne propargyl carbocation propargyl carbanion propargyl free radical y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
7 2D structure drawing hem 314 Beauchamp nitrile protonated nitrile nitrile enolate () carboxylic acid carboxylate anion protonated carboxylic acid carboxylate dianion y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
8 2D structure drawing hem 314 Beauchamp y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc o amide amide anion protonated amide () ester ester enolate protonated ester
9 2D structure drawing hem 314 Beauchamp y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc 3 l 3 l 2 l acid chloride acid chloride enolate (unstable to elimination, forms ketene) l poor due to inefficient overlap of 3p chlorine orbital with 2p carbon orbital l l l l l more times (around the ring) 2 more times (around the ring) 2 more times (around the ring)
10 2D structure drawing hem 314 Beauchamp 3 2 F 3 F 3 F F use zig-zag drawing for sp 3 chains fluoroalkane F F F till to do F 3 F 3 F F y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
11 2D structure drawing hem 314 Beauchamp antidisestablishmenttarianism - opposition to disestablishmentof a church or religoius body an - ti - dis - es - tab - lish - ment - ta - ri - an - ism Break a complicated problem down into simpler parts. 3 2 ( 3 ) ( 2 ) 2 () 2 () ()' ()' l 2 l 2 ( 2 )' 2 ( 3 ) ( 3 ) 2 ( 2 3 )' ( 2 3 )' 3 2 ( 3 ) ( 3 ) 3 () () ( 3 ) 3 2 ( 2 )' y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc
12 2D structure drawing hem 314 Beauchamp y:\files\classes\314\314 pecial andouts\drawing 2D functional groups home.doc ' ' l l ' 3 ' 3 ' ' ketone alkene nitroso nitrite alcohol azide diazonium aldehyde alkyne nitro nitro alkyne alkyne nitrile ester ketone alkene alcohol carboxylic acid alkene alkene nitrile alkyne nitrile thio ether / sulfide amide sulfonamide sulfonamide amide ether ether amine t-butyl ester methyl sulfonate amine thio ether sulfide thiol acid chloride sulfonyl chloride thiol alcohol carboxylic acid sulfonic acid alcohol aldehyde aldehyde ketone
2Dstructuredrawing Chem314 Beauchamp
2Dstructuredrawing hem314 Beauchamp 3 2 3 3 2 2 3 2 2 3 2 2 (neutral) (cation) (anion) (free radical) use zig-zag drawing for sp 3 chains 1 o carbocation 1 o carbanion 1 o free radical 3 3 3 3 3 3 (cation)
antidisestablishmenttarianism an-ti-dis-es-tab-lish-ment-ta-ri-an-ism
What do you do when you encounter a very long, difficult word? 1 antidisestablishmenttarianism break it up into syllables: an-ti-dis-es-tab-lish-ment-ta-ri-an-ism meaning: antidisestablishmenttarianism
Organic Resonance Systems
rganic esonance Systems ommon, Possible Patterns of esonance There are four common resonance patterns that we encounter, using two donor sites and two acceptor sites. onor electrons () can come from lone
Acid/Base stuff Beauchamp 1
cid/base stuff Beauchamp 1 Problems You should be able to match a pk a value with its acid in each group below and explain the differences. You should be able to draw an arrow-pushing mechanism with general
Chapter 2. Molecular Representations
hapter 2. Molecular Representations 3 () 3 ( 3 ) 2 3 3 3 8 Lewis (Kekule) structure ondensed and par6ally condensed structure Skeletal (bond- line) structure Molecular formula Amoxicillin a widely prescribed
CHEMISTRY Topic #1: Functional Groups and Drawing Organic Molecules Fall 2014 Dr. Susan Findlay
EMISTRY 2500 Topic #1: Functional Groups and Drawing rganic Molecules Fall 2014 Dr. Susan Findlay Drawing rganic Molecules (Basics) Recall the steps for drawing Lewis structures in EM 1000: 1. Determine
Chemistry 1A Spring 1998 Exam #4 KEY Chapters 9 & 10
Chemistry 1A Spring 1998 Exam #4 KEY Chapters 9 & 10 For each of the following, write the word, words, or number in each blank that best completes each sentence. (2 points each) 1. A(n) molecular orbital
Chapter 2 Molecular Representations
hapter 2 Molecular Representations Structural Formulas and ondensed Structures Because organic compounds are molecular in nature, the additional information conveyed in structural formulas is sometimes
Classes of Organic Compounds
Unit 1 Functional Groups Depicting Structures of rganic ompounds Lewis Structures ondensed structural formulas Line angle drawings 3-dimensional structures Resonance Structures Acid-Base Reactions urved
OAT Organic Chemistry - Problem Drill 19: NMR Spectroscopy and Mass Spectrometry
OAT Organic Chemistry - Problem Drill 19: NMR Spectroscopy and Mass Spectrometry Question No. 1 of 10 Question 1. Which statement concerning NMR spectroscopy is incorrect? Question #01 (A) Only nuclei
5. Stereochemical Analysis. 7. Dipole Moments and Inductive versus Resonance Effects. 8. Types of isomers from a given formula. 9. Physical Properties
hem 201 Sample Midterm Beauchamp ame Problems Points redit 1. Functional Group omenclature (1 large structure) 2. Lewis Structures, Resonance, Formal harge 3. yclohexane onformations, 2 substituents, ewman
Electrophile = electron loving = any general electron pair acceptor = Lewis acid, (often an acidic proton)
314 Arrow Pushing practice/eauchamp 1 Electrophile = electron loving = any general electron pair acceptor = Lewis acid, (often an acidic proton) ucleophile = nucleus/positive loving = any general electron
Introduction to Organic Chemistry
Introduction to rganic hemistry 59 Introduction to rganic hemistry andout 3 - chanism u u http://burton.chem.ox.ac.uk/teaching.html rganic hemistry J. layden,. Greeves, S. Warren Stereochemistry at a Glance
MOLECULAR REPRESENTATIONS AND INFRARED SPECTROSCOPY
MOLEULAR REPRESENTATIONS AND INFRARED SPETROSOPY A STUDENT SOULD BE ABLE TO: 1. Given a Lewis (dash or dot), condensed, bond-line, or wedge formula of a compound draw the other representations. 2. Give
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
Keynotes in Organic Chemistry
Keynotes in Organic Chemistry Second Edition ANDREW F. PARSONS Department of Chemistry, University of York, UK Wiley Contents Preface xi 1 Structure and bonding 1 1.1 Ionic versus covalent bonds 1 1.2
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
Available chemicals from the catalog (the starting sources of carbon compounds will continually decrease as we learn new reactions.
ucleophilic ubstitution & Elimination Chemistry Beauchamp 1 Available chemicals from the catalog (the starting sources of carbon compounds will continually decrease as we learn new reactions. ources of
Chapter 2 Acids and Bases. Arrhenius Acid and Base Theory. Brønsted-Lowry Acid and Base Theory
hapter 2 Acids and Bases A significant amount of chemistry can be described using different theories of acids and bases. We ll consider three different acid-base theories (listed in order of increasing
Chem 201 Sample Midterm Beauchamp
hem 201 Sample Midterm Beauchamp Exams are designed so that no one question will make or break you. The best strategy is to work steadily, starting with those problems you understand best. Partial credit
Carbon and Its Compounds
Chapter 1 Carbon and Its Compounds Copyright 2018 by Nelson Education Limited 1 1.2 Organic Molecules from the Inside Out I: The Modelling of Atoms Copyright 2018 by Nelson Education Limited 2 s orbitals:
Identifying Functional Groups. Why is this necessary? Alkanes. Why is this so important? What is a functional group? 2/1/16
Identifying Functional Groups The Key to Survival Why is this so important? ver and over again, you will be asked to do reactions, the details to which you will receive in lecture and via your textbook.
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
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
CHAPTER 2: Structure and Properties of Organic Molecules
1 HAPTER 2: Structure and Properties of Organic Molecules Atomic Orbitals A. What are atomic orbitals? Atomic orbitals are defined by special mathematical functions called wavefunctions-- (x, y, z). Wavefunction,
KOT 222 Organic Chemistry II
KOT 222 Organic Chemistry II Course Objectives: 1) To introduce the chemistry of alcohols and ethers. 2) To study the chemistry of functional groups. 3) To learn the chemistry of aromatic compounds and
DAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 5 Dr Ali El-Agamey 1 Energy Diagram of One-Step Exothermic Reaction The vertical axis in this graph represents the potential energy. The transition
S N 2 and E2 Mechanisms (strong base/nucleophile competition reacting at a carbon or reacting at a proton)
Electrophile (Lewis Acid) = electron loving = any general electron pair acceptor (can also be an acidic proton = onsted acid) ucleophile (Lewis Base) = nucleus/positive loving = any general electron pair
MULTIPLE CHOICE 2 points each
Name: Date: Score: / 110 Chapter 1/ TEST 1 OPEN BOOK KEY Organic Chemistry MULTIPLE CHOICE 2 points each 1. An atom of which element would have an electron configuration of 1s 2 2s 2 2p 6 3s 2 3p 1? a.
Chapter 19: Amines. Introduction
Chapter 19: Amines Chap 19 HW: (be able to name amines); 37, 39, 41, 42, 44, 46, 47, 48, 53-55, 57, 58 Introduction Organic derivatives of ammonia. Many are biologically active. Chap 19: Amines Slide 19-2
Chem 201 Midterm Winter, 2013 Beauchamp
hem 0 Midterm Winter, 0 Beauchamp Name Problems Points redit. Functional Group Nomenclature. Degrees of Unsaturation & Functional Groups or Various Nomenclature Terms. D structure, Functional Groups 0.
ORGANIC - EGE 5E CH. 2 - COVALENT BONDING AND CHEMICAL REACTIVITY
!! www.clutchprep.com CONCEPT: HYBRID ORBITAL THEORY The Aufbau Principle states that electrons fill orbitals in order of increasing energy. If carbon has only two unfilled orbitals, why does it like to
Answers to Assignment #5
Answers to Assignment #5 A. 9 8 l 2 5 DBE (benzene + 1 DBE) ( 9 2(9)+2-9 8+1+1 = 10 ˆ 5 DBE) nmr pattern of two doublets of equal integration at δ7.4 and 7.9 ppm means the group (the δ7.9 shift) IR band
ORGANIC - BROWN 8E CH.1 - COVALENT BONDING AND SHAPES OF MOLECULES
!! www.clutchprep.com CONCEPT: WHAT IS ORGANIC CHEMISTRY? Organic Chemistry is the chemistry of life. It consists of the study of molecules that are (typically) created and used by biological systems.
(2) Read each statement carefully and pick the one that is incorrect in its information.
Organic Chemistry - Problem Drill 17: IR and Mass Spectra No. 1 of 10 1. Which statement about infrared spectroscopy is incorrect? (A) IR spectroscopy is a method of structure determination based on the
Lecture Topics: I. Electrophilic Aromatic Substitution (EAS)
Reactions of Aromatic Compounds Reading: Wade chapter 17, sections 17-1- 17-15 Study Problems: 17-44, 17-46, 17-47, 17-48, 17-51, 17-52, 17-53, 17-59, 17-61 Key Concepts and Skills: Predict and propose
Chapter 1: Atomic and Molecular Structure
Chapter 1: Atomic and Molecular Structure LEARNING OBJECTIVES Determine the number of valence and/or core electrons for an atom or ion. Multiple Choice: 1, 6, 11 Interpret the electron configuration and
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURES 1-2. Dr Ali El-Agamey LEARNING OUTCOMES LECTURES 1-2
DAMIETTA UNIVERSITY EM-103: BASI RGANI EMISTRY LETURES 1-2 Dr Ali El-Agamey ١ LEARNING UTMES LETURES 1-2 Appreciate the importance of organic chemistry. Draw the structures of organic compounds using Lewis,
Synthetic possibilities Chem 315 Beauchamp 1
Synthetic possibilities hem Beauchamp Propose reasonable syntheses f the following target molecules (TM-#). You can use the given starting materials and any typical ganic reagents studied in our course
Carbon Compounds. Chemical Bonding Part 2
Carbon Compounds Chemical Bonding Part 2 Introduction to Functional Groups: Alkanes! Alkanes Compounds that contain only carbons and hydrogens, with no double or triple bonds.! Alkyl Groups A part of a
Amines. Amines are organic compounds containing a nitrogen functionality. primary secondary tertiary quaternary
Amines Amines are organic compounds containing a nitrogen functionality Depending upon the number of alkyl, or aryl, groups attached to nitrogen determines its classification, or order 2 primary secondary
Cl 7 8 N 9 H 6 HS 4. 2-(5,5-dimethyl-3-chlorocyclopent-2-enyl)-5-oxo-6-methyl-7-cyanoheptyl 2-hydroxy-3,3-dimethyl-4-(1-mercapto-
hem 0 Sample Midterm Beauchamp Exams are designed so that no one question will make or break you. The best strategy is to work steadily, starting with those problems you understand best. Partial credit
Carbon-heteroatom single bonds basic C N C X. X= F, Cl, Br, I Alkyl Halide C O. epoxide Chapter 14 H. alcohols acidic H C S C. thiols.
hapter 13: Alcohols and Phenols 13.1 Structure and Properties of Alcohols Alkanes arbon - arbon Multiple Bonds arbon-heteroatom single bonds basic Alkenes X X= F, l,, I Alkyl alide amines hapter 23 nitro
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.).
Nucleophilic Addition Reactions of Carboxylic Acid Derivatives
Lecture 5: bjectives: Nucleophilic Addition eactions of Carboxylic Acid Derivatives By the end of this lecture you will be able to: draw the mechanism of a nucleophilic addition-elimination reaction with
CHEM1902/ N-8 November Consider the following reaction sequences beginning with the carboxylic acid, E.
CEM1902/4 2014--8 ovember 2014 Consider the following reaction sequences beginning with the carboxylic acid, E. 6 ame compounds E and G. E: propionic acid G: methyl propionate Propose structures for compounds
Problems. 8. Stereochemical Analysis Physical Properties, Forces of Interaction Resonance, Curved Arrows, Formal Charge, Polarity 15
hem 201 Midterm Exam Winter, 2017 Beauchamp Name Problems Points 1. Functional Group Nomenclature (1 large structure) 30 2. Degrees of Unsaturation & Functional Groups (many different functional groups)
Dienes & Polyenes: An overview and two key reactions (Ch )
Dienes & Polyenes: An overview and two key reactions (h. 14.1-14.5) Polyenes contain more than one double bond and are very common in natural products (ex: carotene). Diene chemistry applies to trienes,
Problems Points Credit
hem 201 Midterm Spring, 2018 Beauchamp ame KEY Problems Points redit 1. Functional Group omenclature (1 large structure) 30 2. esonance, Formal harge, Arrows 18 3. yclohexane onformations, ewman Projections
Chem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below.
hem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below. TP l Et step 8 4 5 eagents used in synthesis A B D E F a DMF (solvent) 1. (i-pr) 2 Li (LDA)/TF
Molecular Geometry: VSEPR model stand for valence-shell electron-pair repulsion and predicts the 3D shape of molecules that are formed in bonding.
Molecular Geometry: VSEPR model stand for valence-shell electron-pair repulsion and predicts the 3D shape of molecules that are formed in bonding. Sigma and Pi Bonds: All single bonds are sigma(σ), that
Key ideas: In EAS, pi bond is Nu and undergoes addition.
Objective 7. Apply addition and elimination concepts to predict electrophilic aromatic substitution reactions (EAS) of benzene and monosubstituted benzenes. Skills: Draw structure ID structural features
R N R N R N. primary secondary tertiary
Chapter 19 Amines omenclature o assification of amines Amines are classified as 1, 2, or 3 based on how many R groups are attached to the nitrogen R R R R R R primary secondary tertiary When there are
A REVIEW OF GENERAL CHEMISTRY: ELECTRONS, BONDS AND MOLECULAR PROPERTIES
A REVIEW OF GENERAL CEMISTRY: ELECTRONS, BONDS AND MOLECULAR PROPERTIES A STUDENT SOULD BE ABLE TO: 1. Draw Lewis (electron dot and line) structural formulas for simple compounds and ions from molecular
When H and OH add to the alkyne, an enol is formed, which rearranges to form a carbonyl (C=O) group:
Next Up: Addition of, : The next two reactions are the Markovnikov and non-markovnikov additions of and to an alkyne But you will not see alcohols form in this reaction! When and add to the alkyne, an
Ch.2 Polar Bonds and Their Consequences. 2.1 Polar Covalent Bonds and Electronegativity. polar covalent bonds: electron distribution is unsymmetrical
2.1 Polar ovalent Bonds and Electronegativity polar covalent bonds: electron distribution is unsymmetrical Ionic haracter δ+ δ- + - X Y X Y X Y symmetrical covalent bond polar covalent bond ionic bond
2.1 Representing Molecules
2.1 Representing Molecules Notice that the molecular formula would be inadequate to distinguish between propanol and isopropanol. Practice converting from one type of representation to another with Skillbuilder
Four new mechanisms to learn: S N 2 vs E2 and S N 1 vs E1
cleophilic ubstitution & Elimination hemistry 1 Four new mechanisms to learn: vs E2 and 1 vs E1 = substitution = a leaving group () is lost from a carbon atom () and replaced by nucleophile (:) = nucleophilic
Objective 3. Draw resonance structures, use curved arrows, determine extent of delocalization. Identify major/minor contributor.
Objective 3 Draw resonance structures, use curved arrows, determine extent of delocalization. Identify major/minor contributor. Structure Should Fit Experimental Data The chemical formula of benzene is
CHE1502. Tutorial letter 203/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry
E1502/203/1/2016 Tutorial letter 203/1/2016 General hemistry 1B E1502 Semester 1 Department of hemistry This tutorial letter contains the answers to the questions in assignment 3. FIRST SEMESTER: KEY T
Chapter 1 Bonding and Isomerism
Chapter 1 Bonding and Isomerism Ionic Compounds: e-are transferred; Cation (+) & anion (-). Opposite charge creates bond. Occurs when compound is made of a metal & a nonmetal. Electron dot structures for:
Acid-Base -Bronsted-Lowry model: -Lewis model: -The more equilibrium lies to the right = More [H 3 O + ] = Higher K a = Lower pk a = Stronger acid
![Acid-Base -Bronsted-Lowry model: -Lewis model: -The more equilibrium lies to the right = More [H 3 O + ] = Higher K a = Lower pk a = Stronger acid](/thumbs/95/123929992.jpg "Acid-Base -Bronsted-Lowry model: -Lewis model: -The more equilibrium lies to the right = More [H 3 O + ] = Higher K a = Lower pk a = Stronger acid")
Revision Hybridisation -The valence electrons of a Carbon atom sit in 1s 2 2s 2 2p 2 orbitals that are different in energy. It has 2 x 2s electrons + 2 x 2p electrons are available to form 4 covalent bonds.
1. methyl 2. methylene 3. methine 4. primary 5. secondary 6. tertiary 7. quarternary 8. isopropyl
hem 201 Sample Midterm Beauchamp Exams are designed so that no one question will make or break you. The best strategy is to work steadily, starting with those problems you understand best. Make sure you
Chapter 19. Carbonyl Compounds III Reaction at the α-carbon
Chapter 19. Carbonyl Compounds III Reaction at the α-carbon There is a basic hydrogen (α hydrogen) on α carbon, which can be removed by a strong base. 19.1 The Acidity of α-hydrogens A hydrogen bonded
Synthesis of Nitriles a. dehydration of 1 amides using POCl 3 : b. SN2 reaction of cyanide ion on halides:
I. Nitriles Nitriles consist of the CN functional group, and are linear with sp hybridization on C and N. Nitriles are non-basic at nitrogen, since the lone pair exists in an sp orbital (50% s character
Chapter 8 Chemical Bonding
Chapter 8 Chemical Bonding Types of Bonds Ionic Bonding Covalent Bonding Shapes of Molecules 8-1 Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Table 8.1 Two
CHEM 203. Midterm Exam 1 October 31, 2008 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Midterm Exam 1 ctober 31, 2008 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This exam contains 8 pages Time: 1h 30 min 1. / 15 2. / 16 3. /
Nucleophilic Substitution & Elimination Chemistry Beauchamp 1
ucleophilic ubstitution & Elimination hemistry Beauchamp 1 Problem 1 - ow can you tell whether the 2 reaction occurs with front side attack, backside attack or front and backside attack? Use the two molecules
19.4 Physical Properties Key: hydrogen bond strength depends on acidity of the hydrogen and basicity of the N or O
Chem 360 Jasperse Ch. 19 Notes. Amines 12 19.4 ysical Properties Key: hydrogen bond strength depends on acidity of the hydrogen and basicity of the N or 1. Water Solubility: All amines hydrogen-bond water
CHCl (vinyl chloride, part of new car smell )
ame Key 1) (20 points) Draw a Lewis dot structure for each of the following molecules; show all lone pairs. Indicate the hybridization at all atoms except hydrogen, chlorine, and fluorine. (a) 2 (b) C
Chapter 9 Aldehydes and Ketones Excluded Sections:
Chapter 9 Aldehydes and Ketones Excluded Sections: 9.14-9.19 Aldehydes and ketones are found in many fragrant odors of many fruits, fine perfumes, hormones etc. some examples are listed below. Aldehydes
C h a p t e r F o u r t e e n: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
C h a p t e r F o u r t e e n: Structure Determination: Mass Spectrometry and Infrared Spectroscopy Cl OH Cl An electron ionization mass spectrum of 2,5-dichlorophenol CHM 323: Summary of Important Concepts
Chapter 3 Acids and Bases
hapter 3 Acids and Bases Basic Definitions Associated with Acids and Bases Molecular Definitions of Acids and Bases Molecular Models of Selected Acids Brønsted-Lowry Theory 1. In a Brønsted-Lowry reaction,
CHEMISTRY 341. Final Exam Tuesday, December 16, Problem 1 15 pts Problem 9 8 pts. Problem 2 5 pts Problem pts
CEMISTRY 341 Final Exam Tuesday, December 16, 1997 Name NAID Problem 1 15 pts Problem 9 8 pts Problem 2 5 pts Problem 10 21 pts Problem 3 26 pts Problem 11 15 pts Problem 4 10 pts Problem 12 6 pts Problem
4. Single > Double > Triple [bond length]
![4. Single > Double > Triple [bond length]](/thumbs/72/67530010.jpg "4. Single > Double > Triple [bond length]")
1. Sigma bonds are significantly stronger than pi bonds. This is because sigma bonds allow for electron density to be concentrated to a much larger degree between the two nuclei. The lowest energy state
Chapter 25 Organic and Biological Chemistry
Chapter 25 Organic and Biological Chemistry Organic Chemistry The chemistry of carbon compounds. Carbon has the ability to form long chains. Without this property, large biomolecules such as proteins,
California State Polytechnic University, Pomona
alifornia State Polytechnic University, Pomona 2-1 Dr. Laurie S. Starkey, rganic hemistry M 314, Wade hapter 2: Structure and Physical Properties of rganic Molecules hapter utline 1) rbitals and Bonding
Electronegativity Scale F > O > Cl, N > Br > C, H
Organic Chem Chapter 12 Alkanes Organic chemistry is the study of carbon compounds. Carbon has several properties that are worth discussing: Tetravalent Always forms 4 bonds Can form multiple bonds (double
Aldehydes and Ketones: Nucleophilic Addition Reactions
Aldehydes and Ketones: Nucleophilic Addition Reactions Why this Chapter? Much of organic chemistry involves the chemistry of carbonyl compounds Aldehydes/ketones are intermediates in synthesis of pharmaceutical
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
SPECTROSCOPY MEASURES THE INTERACTION BETWEEN LIGHT AND MATTER
SPECTROSCOPY MEASURES THE INTERACTION BETWEEN LIGHT AND MATTER c = c: speed of light 3.00 x 10 8 m/s (lamda): wavelength (m) (nu): frequency (Hz) Increasing E (J) Increasing (Hz) E = h h - Planck s constant
Mass Spectrometry Instrumentation
Mass Spectrometry Instrumentation A mass spectrometer is composed of an inlet system (which introduces the sample to the instrument and vaporizes the sample) A molecular leak (which produces a steady stream
2. Separate the ions based on their mass to charge (m/e) ratio. 3. Measure the relative abundance of the ions that are produced
I. Mass spectrometry: capable of providing both quantitative and qualitative information about samples as small as 100 pg (!) and with molar masses in the 10 4-10 5 kdalton range A. The mass spectrometer
ALCOHOLS AND PHENOLS
ALCOHOLS AND PHENOLS ALCOHOLS AND PHENOLS Alcohols contain an OH group connected to a a saturated C (sp3) They are important solvents and synthesis intermediates Phenols contain an OH group connected to
ζ ε δ γ β α α β γ δ ε ζ
hem 263 Nov 17, 2016 eactions at the α-arbon The alpha carbon is the carbon adjacent to the carbonyl carbon. Beta is the next one, followed by gamma, delta, epsilon, and so on. 2 ε 2 δ 2 γ 2 2 β α The
"You can't go back and change the beginning, but you can start where you are and change the ending." C.S. Lewis. Chem 201 Midterm.
hem 201 Midterm Fall, 2017 Beauchamp ame Problems Points redit 1. Functional Group omenclature (1 large structure) 2. Types of Isomers, Degrees of Unsaturation or common nomenclature terms or functional
Learning Organic Chemistry
Objective 1 Represent organic molecules with chemical formulas, expanded formulas, Lewis structures, skeletal structures. Determine shape (VSEPR), bond polarity, and molecule polarity. Identify functional
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
Background Information
ackground nformation ntroduction to Condensation eactions Condensation reactions occur between the α-carbon of one carbonyl-containing functional group and the carbonyl carbon of a second carbonyl-containing
Introduction to Organic Chemistry
PART 1 Introduction to Organic Chemistry Chapter 1. Structure, bonding, acid-base 2. Nomenclature, physical properties, drawing structure Chapter 1 Structure and Bonding Acids and Bases Electronic structure
Amines Reading Study Problems Key Concepts and Skills Lecture Topics: Amines: structure and nomenclature
Amines Reading: Wade chapter 19, sections 19-1-19-19 Study Problems: 19-37, 19-39, 19-40, 19-41, 19-44, 19-46, 19-47, 19-48, 19-51, 19-54 Key Concepts and Skills: Explain how the basicity of amines varies
Table 8.2 Detailed Table of Characteristic Infrared Absorption Frequencies
Table 8.2 Detailed Table of Characteristic Infrared Absorption Frequencies The hydrogen stretch region (3600 2500 cm 1 ). Absorption in this region is associated with the stretching vibration of hydrogen
Chem 201 Final. Beauchamp
hem 201 Final Winter, 2018 Beauchamp ame KEY Problems Points redit 1. Functional Group omenclature (1 large structure) 0 2. Lewis tructures, esonance, Formal harge 18. yclohexane onformations, 2 substituents,
2. See spectra below. Carboxylic Acid (Note O-H and C=O) FIGURE 1
1. We can compare a vibrating bond (in only one dimension, ignoring swaying motions) to a mass on a spring. The bond roughly follows Hooke s Law and either atom can be compared to the mass. A stronger
CHAPTER 19: CARBONYL COMPOUNDS III
CHAPTER 19: CARBONYL COMPOUNDS III A hydrogen bonded to a carbon adjacent to a carbonyl carbon is sufficiently acidic to be removed by a strong base. The carbon adjacent to a carbonyl carbon is called
Organic Chemistry 6 th Edition Paula Yurkanis Bruice. Chapter 1. Electronic Structure and Bonding. Acids and Bases Pearson Education, Inc.
Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 1 Electronic Structure and Bonding Acids and Bases 2011 Pearson Education, Inc. 1 Organic Chemistry Carbon-containing compounds were once considered
REALLY, REALLY STRONG BASES. DO NOT FORGET THIS!!!!!
CHEM 345 Problem Set 4 Key Grignard (RMgX) Problem Set You will be using Grignard reagents throughout this course to make carbon-carbon bonds. To use them effectively, it will require some knowledge from
Welcome to C341!! Chapter 1 & 2: Review of General Chemistry
Welcome to C341!! Chapter 1 & 2: Review of General Chemistry What will we do today? 1. Review of the syllabus together. 2. Discuss course structure and textbook. You will use the entire textbook between
Topic 9. Aldehydes & Ketones
Chemistry 2213a Fall 2012 Western University Topic 9. Aldehydes & Ketones A. Structure and Nomenclature The carbonyl group is present in aldehydes and ketones and is the most important group in bio-organic
Overview of Types of Organic Reactions and Basic Concepts of Organic Reaction Mechanisms
Overview of Types of Organic Reactions and Basic Concepts of Organic Reaction Mechanisms Dr. Solomon Derese 1 A chemical reaction is the transformation of one chemical or collection of chemicals into another