Available chemicals from the catalog (the starting sources of carbon compounds will continually decrease as we learn new reactions.
|
|
- Anna Rich
- 5 years ago
- Views:
Transcription
1 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 carbon - you can invoke these whenever needed: C 4 ources of carbon - you can until we cover reactions that will make them from the above compounds, then they will go away: Commercially available chemicals and reagents - you can invoke these whenever you need them. 2 Cl Cl 2 I P bromine chlorine hydrogen hydrogen hydrogen sulfuric phosphoric nitric acid water ammonia hydrogen chloride bromide iodide acid acid peroxide alts / ionic substances hydride 2 C =Cor azide K amide (excellent nucleophile) nitrite hydroxide cyanide C 2 n-butyl lithium (very strong base or nucleophile, use anytime) hydrogen sulfide diisopropylamine Cl 1. g(ac) 2 / 2. B 4 dithiane meta chloroperbenzoic acid (mcpba) 1. g(ac) 2 / 2 2. B 4 Various s Mg magnesium lithium TP (protect -) 3 C methyl lithium Ph potassium hydride 2 C phenyl lithium B = -bromosuccinimide (supplies free radical bromine for allylic & benzylic substitution) Ph pre aldehydes/ketones P Ph triphenylphosphine (to make Wittig salts) / 3 in ammonia (Birch reagent) CCl 3 chloroform C 3 bromoform Zn zinc Pd / 2 palladium & hydrogen B borohydride (nucleophylic hydride) phthalimide (an imide) C 2 I 2 Zn / Cu immons mith reagent Pd / 2 quinoline (ndlar's cat) toluene sulfonic acid = Ts (very strong organic acid) ethanoic acid a carboxylic acid) pre alds / kets Cr 3ozone reactions pyridine 1. 3,-78 o (PCC) C 2. C 3 C ,-78 o C 2. B ,-78 o C , gx 2 (mecuric salts) Al lithium aluminumhydride = LA (very strong nucleophilic hydride) (AlD 4 too) ketone (a carbonyl) pre alds / kets C 2 carbon dioxide Mn Cr 2 / 3 + (Jones) diborane diborane use w/ alkenes use w/ alkenes 1. B 1. B / 2. 2 /C 3 Cl I K potassium permanganate osmium tetroxide 2 2 ethylene hydrazine pyrrolidine glycol (Wolff-Kishner) (enamines) (protect C=) Cl = Ts-Cl (tosyl chloride) makes into tosylates t-butyl alcohol (use to make t-butoxide) s Cu cuprous bromide B C cyanoborohydride (nucleophylic hydride) (BD 4 too) = py pyridine = proton sponge dialkylborane use w/ alkynes 1. B / Lewis acids Al 3 Fe 3 BF 3 Cl 2 P 3 3 etc. Z:\files\classes\315\315 andouts\available chemicals, syn targets & chem catalog.doc
2 ucleophilic ubstitution & Elimination Chemistry Beauchamp 2 C1 through C7 - examples (no stereochemistry indicated; enantiomers and diastereomers). oon any of these will be within our grasp ( and more). 1C 2C 3C 4C 3 C 5C 6C 6C 6C Z:\files\classes\315\315 andouts\available chemicals, syn targets & chem catalog.doc
3 ucleophilic ubstitution & Elimination Chemistry Beauchamp 3 Group A (bromo compounds from free radical substitution at sp 3 C- positions, from alcohols and alkenes) make various ways 3 C given until alkenes Group C ( from methyl and primary bromides and hydroxide via 2 reactions; from secondary and tertiary bromides and water via 1, but rearrangements are possible; also from alkenes, carbonyls and epoxides) make various ways 3 C Group D (esters from methyl, primary and secondary bromides and carboxylates (acetate, here) via 2 reactions, esters can be hydrolyzed to alcohols via acyl substitution with hydroxide, and via 1 at tertiary X and various other methods we will learn) Group F (ethers from methyl and primary bromides and alkoxides via 2 reactions, t-butoxide reacts mostly by E2, 2 o X and 3 o X mainly form E2 products too) (ethers from secondary and tertiary bromides and alcohols via 1, but rearrangements are possible) Z:\files\classes\315\315 andouts\available chemicals, syn targets & chem catalog.doc
4 ucleophilic ubstitution & Elimination Chemistry Beauchamp 4 Epoxides are special ethers that can be made from bromohydrins + base or alkenes + mcpba (later). The large ring strain allows them to be easily opened by strong nucleophile/bases or in strong acid. Group G (amines from methyl, primary and secondary bromides and conjugate base of phthalimide via 2 reactions, the alkyl imide can be hydrolyzed to primary amines via two acyl substitutions with hydroxide, see mechanism above) or make azides via 2 reactions and then react using 1. Al 4, 2. workup. Group (tosylates formed from alcohols and tosyl chloride/pyridine via acyl substitution reaction, converts from poor leaving group into a very good leaving group similar to iodide) 3 C Ts Ts Ts Ts Ts Ts Ts Ts Ts Ts Ts Ts Group I (alkenes formed by E2 reaction with potassium t-butoxide and - compounds or make via E1 reactions of and 2 4 / ) Group J (make ethyne or propyne using dibromo ethane or propane and double E2 reactions using 2 ), ( make other alkynes from terminal acetylide and methyl or primary X via 2 reaction; two reactions are possible in stepwise manner on both sides of ethyne, can put one or two groups on, mostly E2 reaction at 2 o - and only E2 at 3 o X), can use zipper reaction to move alkyne to end position along unsubstituted linear chain and start over. Z:\files\classes\315\315 andouts\available chemicals, syn targets & chem catalog.doc
5 ucleophilic ubstitution & Elimination Chemistry Beauchamp 5 Group K (nitriles from cyanide and methyl, primary and secondary X via 2 reaction, reaction, only E2 reaction at 3 o -; or make from primary amides + Cl 2 ) Group L (thiols from hydrogen sulfide and methyl, primary and secondary X via 2 reaction, reaction, only E2 reaction at 3 o - in our course), Can do reaction a second time and make sulfides, C 3 C Group M (synthesis of ketones from 2-propanone (acetone) via 2 with propanone enolate at methyl, 1 o, 2 o X. nly E1 at 3 o X. Make propanone enolate from propanone and lithium diisopropylamide = LDA at 78 o C, made from diisopropylamine and n-butyl lithium shown on page 2 under useful acid/base reactions.) Z:\files\classes\315\315 andouts\available chemicals, syn targets & chem catalog.doc
6 ucleophilic ubstitution & Elimination Chemistry Beauchamp 6 Group (synthesis of esters from ethyl ethanoate (ethyl acetate) via 2 using an ester enolate at methyl, 1 o, 2 o X. nly E1 at 3 o X. Make ester enolate from ester and lithium diisopropylamide = LDA at 78 o C, made from diisopropylamine and n-butyl lithium shown on page 2 under useful acid/base reactions.) LDA = lithium diisopropylamide ethyl ethanoate ethyl acetate 1 acid/base rxn -78 o C carbanion nucleophile 2 rxn X new bond These are examples there are other possibilities. Make carbonyl compounds from alcohols (aldehydes (PCC), ketones (PCC or Jones) and carboxylic acids (Jones). There are many other methods too. aldehydes carboxylic acids (remember these can be made into esters) ketones Make acid chlorides from carboxylic acids + thionyl chloride (Cl 2 ). Acid chlorides can be made into many things including esters, amides and anhydrides (for now). Z:\files\classes\315\315 andouts\available chemicals, syn targets & chem catalog.doc
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
More informationChem 315/316 Reactions. Bromo organic compounds C1 & C2 carbon skeletons C3 carbon skeletons C4 carbon skeletons. Alcohols. Chem 316 / Beauchamp 1
hem 316 / Beauchamp 1 hem 315/316 eactions Name available sources of carbon 4 3 NaN methyl 3 2 ethyl 3 2 2 n-propyl 3 3 isopropyl 2 3 2 3 3 2 2 3 3 3 n-butyl sec butyl t-butyl phenyl available until topic
More informationS 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
More informationProducts from reactions of carbon nucleophiles and carbon electrophiles used in the 14 C Game and our course:
synthesis strategies, hem / / Beauchamp roducts from reactions of carbon nucleophiles and carbon electrophiles used in the Game and our course: arbon electrophiles methyl primary organolithium reagents
More informationNucleophilic 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.).
More informationElectrophile = 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
More informationThese same reaction schemes are available without the mechanistic details, so you can practice filling in those details.
314/315 reactions and mechanisms through topic 11 and some of topic 12 1 These same reaction schemes are available without the mechanistic details, so you can practice filling in those details. Problems
More informationFour new mechanisms to learn: S N 2 vs E2 and S N 1 vs E1
ucleophilic ubstitution & Elimination hemistry 1 Four new mechanisms to learn: 2 vs E2 and 1 vs E1 = substitution = a leaving group () is lost from a carbon atom () and replaced by nucleophile (u:) = nucleophilic
More informationFour 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
More informationNucleophilic 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
More informationModule9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area
1 CHEMISTRY 263 HOME WORK Lecture Topics: Module7. Hydrogenation of Alkenes The Function of the Catalyst - Syn and anti- addition Hydrogenation of Alkynes - Syn- addition of hydrogen: Synthesis of cis-alkenes
More informationCHEMISTRY 263 HOME WORK
Lecture Topics: CHEMISTRY 263 HOME WORK Module7: Hydrogenation of Alkenes Hydrogenation - syn and anti- addition - hydrogenation of alkynes - synthesis of cis-alkenes -synthesis of trans-alkenes Text sections:
More informationCHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Final Exam December 15, 2010 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test contains 15 pages Time: 2h 30 min 1. / 16 2. / 15 3. / 24
More informationKOT 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
More information2Dstructuredrawing 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)
More informationAlcohols. Have seen many reactions to synthesize alcohols: In this chapter we will study reactions of the alcohols
Alcohols ave seen many reactions to synthesize alcohols: In this chapter we will study reactions of the alcohols Oxidation Need to understand the nomenclature of organic reduction/oxidation In general
More informationPhysical Properties. Alcohols can be: CH CH 2 OH CH 2 CH 3 C OH CH 3. Secondary alcohol. Primary alcohol. Tertiary alcohol
Chapter 10: Structure and Synthesis of Alcohols 100 Physical Properties Alcohols can be: CH 3 CH 3 CH CH 2 OH * Primary alcohol CH 3 OH CH * CH 2 CH 3 Secondary alcohol CH 3 CH 3 * C OH CH 3 Tertiary alcohol
More informationNucleophilic Substitution & Elimination Chemistry Beauchamp 1
cleophilic ubstitution & Elimination hemistry Beauchamp 1 Four mechanisms to learn: vs E2 and 1 vs E1 = substitution = a leaving group () is lost from a carbon atom () and replaced by nucleophile (:) =
More informationLoudon Chapter 23 Review: Amines CHEM 3331, Jacquie Richardson, Fall Page 1
Loudon Chapter 23 eview: Amines CEM 3331, Jacquie ichardson, Fall 2010 - Page 1 This chapter is about the chemistry of nitrogen. We ve seen it before in several places, but now we can look at several reactions
More informationReducing 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 informationCarbon-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
More informationDetailed 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
More informationAldehydes 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
More informationAlcohol 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 informationChapter 20: Carboxylic Acids
1 Chapter 20: Carboxylic Acids I. Introduction: Carboxylic acid structure: Classification of carboxylic acids: A carboxylic acid donates protons by the heterocyclic cleavage of the O-H bond, generating
More informationSuggested solutions for Chapter 28
s for Chapter 28 28 PBLEM 1 ow would you make these four compounds? Give your disconnections, explain why you chose them and then give reagents for the. 2 2 Me S Exercises in basic one- group C X disconnections.
More informationChapter 22: Amines. Organic derivatives of ammonia, NH 3. Nitrogen atom have a lone pair of electrons, making the amine both basic and nucleophilic
hapter 22: Amines. rganic derivatives of ammonia, 3. itrogen atom have a lone pair of electrons, making the amine both basic and nucleophilic 22.1: Amines omenclature. (please read) sp 3 Amines are classified
More information20.3 Alkylation of Enolate Anions
864 APTER 20 ELATE AD TER ARB ULEPILES which precipitates as a yellow solid, provides a positive test for the presence of a methyl ketone The reaction can also be used in synthesis to convert a methyl
More informationLoudon Chapter 10 Review: Alcohols & Thiols Jacquie Richardson, CU Boulder Last updated 4/26/2016
Alcohols (R) and thiols (RS) have many reactions in common with alkyl halides, but they don t do everything exactly the same. The main difference between this and alkyl halide chemistry is that unlike
More informationQuímica Orgânica I. Ciências Farmacêuticas Bioquímica Química AFB QO I 2007/08 1
Química rgânica I Ciências Farmacêuticas Bioquímica Química AFB Q I 2007/08 1 alcohols Adaptado de rganic Chemistry, 6th Edition; Wade rganic Chemistry, 6 th Edition; McMurry AFB Q I 2007/08 2 Typical
More informationCHAPTER 20: MORE ABOUT OXIDATION REDUCTION REACTIONS Oxidation Reduction Reactions of Organic Compounds: An Overview
CHAPTER 20: MORE ABOUT OXIDATION REDUCTION REACTIONS In an oxidation-reduction reaction (redox reaction), one species loses electrons and one gains electrons. The species that loses electrons is oxidized,
More informationTips for taking exams in 852
Comprehensive Tactical Methods in rganic Synthesis W. D. Wulff 1) Know the relative reactivity of carbonyl compounds Tips for taking exams in 852 Cl > > ' > > ' N2 eg: 'Mg Et ' 1equiv. 1equiv. ' ' Et 50%
More informationChem 263 Nov 14, e.g.: Fill the reagents to finish the reactions (only inorganic reagents)
hem 263 ov 14, 2013 More examples: e.g.: Fill the reagents to finish the reactions (only inorganic reagents) Br 2 hv Br a 2 r 4 S 2 or swern oxidation Mg Li 0 0 MgBr Li e.g. : Fill the reagents (any reagents
More informationREALLY, 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
More information(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 informationChem 263 March 7, 2006
Chem 263 March 7, 2006 Aldehydes and Ketones Aldehydes and ketones contain a carbonyl group, in which the carbon atom is doubly bonded to an oxygen atom. The carbonyl group is highly polarized, with a
More information1/4/2011. Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds
Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds The Acidity of the Hydrogens of Carbonyl Compounds: Enolate Anions Hydrogens on carbons to carbonyls are unusually acidic
More informationBut 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 informationChapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group
Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al
More informationChapter 16. Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group. Physical Properties of Aldehydes and Ketones. Synthesis of Aldehydes
Nomenclature of Aldehydes and Ketones Chapter 16 Aldehydes and Ketones I. Aldehydes replace the -e of the parent alkane with -al The functional group needs no number Nucleophilic Addition to the Carbonyl
More informationChapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group
Chapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al
More informationPractice Synthetic Problems: CHEM 235 Page 2
Practice Synthetic Problems: CM 235 Page 2 Syntheses based on diethyl malonate, ethyl acetoacetate, etc. Using diethyl malonate and any other necessary organic reagents, show a synthesis of: a) 2,2-dimethyl-1,3-propanediamine
More informationCHEM 203. Final Exam December 18, 2013 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Your name: Final Exam December 18, 2013 ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test consists of 10 pages Time: 2h 30 min 1. / 20 2. / 20 3.
More informationζ 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
More informationChem 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
More informationLecture 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 informationBasic Organic Chemistry
Basic rganic hemistry ourse code: EM 12162 (Pre-requisites : EM 11122) hapter 06 hemistry of Aldehydes & Ketones Dr. Dinesh R. Pandithavidana ffice: B1 222/3 Phone: (+94)777-745-720 (Mobile) Email: dinesh@kln.ac.lk
More informationSynthesis and Structure of Alcohols Alcohols can be considered organic analogues of water.
Synthesis and Structure of Alcohols Alcohols can be considered organic analogues of water. Alcohols are usually classified as primary, secondary and tertiary. Alcohols with the hydroxyl bound directly
More informationLoudon 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 information896 Chapter 21 Amines H H N R R R N R H R N R H O H R 3 N CH 2 NH 2 NHCH 3
896 Chapter 21 Amines 21.20 Summary Section 21.1 Section 21.2 Section 21.3 Section 21.4 Alkylamines are compounds of the type shown, where R, R, and R are alkyl groups. ne or more of these groups is an
More informationAcid/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
More information2.222 Practice Problems 2003
2.222 Practice Problems 2003 Set #1 1. Provide the missing starting compound(s), reagent/solvent, or product to correctly complete each of the following. Most people in the class have not done this type
More information18.8 Oxidation. Oxidation by silver ion requires an alkaline medium
18.8 Oxidation Oxidation by silver ion requires an alkaline medium Test for detecting aldehydes Tollens reagent to prevent precipitation of the insoluble silver oxide, a complexing agent is added: ammonia
More informationTOK: The relationship between a reaction mechanism and the experimental evidence to support it could be discussed. See
Option G: Further organic chemistry (15/22 hours) SL students study the core of these options and HL students study the whole option (the core and the extension material). TOK: The relationship between
More informationChem 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
More informationN_HW1 N_HW1. 1. What is the purpose of the H 2 O in this sequence?
N_HW1 N_HW1 Multiple Choice Identify the choice that best completes the statement or answers the question. There is only one correct response for each question. 1. What is the purpose of the H 2 O in this
More informationORGANIC - CLUTCH CH ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION
!! www.clutchprep.com CONCEPT: ALDEHYDE NOMENCLATURE Replace the suffix of the alkane -e with the suffix On the parent chain, the carbonyl is always terminal, and receive a location As substituents, they
More informationAdditions to the Carbonyl Groups
Chapter 18 Additions to the Carbonyl Groups Nucleophilic substitution (S N 2andS N 1) reaction occurs at sp3 hybridized carbons with electronegative leaving groups Why? The carbon is electrophilic! Addition
More informationDAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 6 Dr Ali El-Agamey 1 Oxidation States Easy for inorganic salts: CrO 4 2- reduced to Cr 2 O 3. KMnO 4 reduced to MnO 2. Oxidation: Gain of O,
More informationR 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
More informationChapter 10: Carboxylic Acids and Their Derivatives
Chapter 10: Carboxylic Acids and Their Derivatives The back of the white willow tree (Salix alba) is a source of salicylic acid which is used to make aspirin (acetylsalicylic acid) The functional group
More informationLoudon Chapter 23 Review: Amines Jacquie Richardson, CU Boulder Last updated 4/22/2018
This chapter is about the chemistry of nitrogen. We ve seen it before in several places, but now we can look at several reactions that are specific to nitrogen. Amines can be subdivided based on how many
More informationChapter 12: Carbonyl Compounds II
Chapter 12: Carbonyl Compounds II Learning bjectives: 1. Recognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions
More informationChapter 17: Alcohols and Phenols
hapter 17: Alcohols and Phenols sp 3 alcohol phenol (aromatic alcohol) pka~ 16-18 pka~ 10 Alcohols contain an group connected to a saturated carbon (sp 3 ) Phenols contain an group connected to a carbon
More informationALCOHOLS 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
More information1. What is the major organic product obtained from the following sequence of reactions?
CH320 N N_HW1 Multiple Choice Identify the choice that best completes the statement or answers the question. There is only one correct response for each question. Carefully record your answers on the Scantron
More informationAldehydes and Ketones Reactions. Dr. Sapna Gupta
Aldehydes and Ketones Reactions Dr. Sapna Gupta Reactions of Aldehydes and Ketones Nucleophilic Addition A strong nucleophile attacks the carbonyl carbon, forming an alkoxide ion that is then protonated.
More informationMechanical Approach to Drawing 2D, 3D and Resonance Structures from a condensed line formula.
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
More informationAmines. 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
More informationCARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION
CARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION Introduction Several functional groups contain the carbonyl group Carbonyl groups can be converted into alcohols by various reactions Structure of the Carbonyl
More informationChapter 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 informationDouble 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 informationCHEM 203. Final Exam December 18, This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Final Exam December 18, 2013 Your name: This a closed-notes, closed-book exam You may use your set of molecular models This test consists of 10 pages Time: 2h 30 min 1. / 20 2. / 20 3. / 30 4.
More informationROADMAP FOR REACTIONS Chapter 6
RADMAP FR REACTINS Chapter 6 (A) (B) (C) (D) (E) (F) (G) (H) (I) (J) (K) (L) (M) (N) () Regiochemistry: Markovnikov addition to a bond Stereochemistry: anti-addition Regiochemistry: non-markovnikov addition
More informationNomenclature Question
Topic 13: i-licker Slides Beauchamp 1 omenclature Question 2 2 a. 1,2-diamino-5,11-dioxo-6-isopropoxy-7-hydroxy-9-cyanoundec-3E-en-1-one b. 3-cyano-5-hydroxy-6-isopropoxy-7,11-dioxo-10,11-diaminoundec-8E-enal
More informationLearning Guide for Chapter 15 - Alcohols (II)
Learning Guide for Chapter 15 - Alcohols (II) I. Introduction to alcohol reactivity II. Reactions of alcohols with acids III. Reactions of alcohols with electrophiles alogenated phosphorus and sulfur compounds
More informationJEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II. 5 Credit Hours. Prepared by: Richard A. Pierce
JEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II 5 Credit Hours Prepared by: Richard A. Pierce Revised Date: January 2008 by Ryan H. Groeneman Arts & Science Education Dr. Mindy Selsor, Dean
More informationLecture Notes Chemistry Mukund P. Sibi Lecture 36 Synthesis of Amines
Lecture otes hemistry 42-2008 Mukund P. Sibi Synthesis of Amines Amines can be prepared from a variety of starting materials. All of these methods involve functional group transformations. The main methods
More informationAlcohols, Ethers and Epoxides. Chapter Organic Chemistry, 8th Edition John McMurry
Alcohols, Ethers and Epoxides Chapter 17-18 Organic Chemistry, 8th Edition John McMurry 1 Introduction Structure and Bonding Alcohols contain a hydroxy group (OH) bonded to an sp 3 hybridized carbon. 2
More informationThe C-X bond gets longerand weakergoing down the periodic table.
Chapter 10: Organohalides Organic molecules containing halogen atoms (X) bonded to carbon are useful compounds in synthesis and on their own. 10.2 Structure of alkyl halides The C-X bond gets longerand
More informationCh 22 Carbonyl Alpha ( ) Substitution
Ch 22 Carbonyl Alpha () Substitution The overall reaction replaces an H with an E + The acid-catalyzed reaction has an enol intermediate The base-catalyzed reaction has an enolate intermediate Keto-Enol
More informationChapter 19 Substitutions at the Carbonyl Group
Chapter 19 Substitutions at the Carbonyl Group In Chapter 18 Additions to the Carbonyl Groups In Chapter 19 Substitutions at the Carbonyl Group O O - - O - O R Y R C+ Y R Y Nu -Ȳ R N u + Y=goodleavinggroup
More informationChapter 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
More informationOrganic Chemistry 1 CHM 2210 Exam 4 (December 10, 2001)
Exam 4 (December 10, 2001) Name (print): Signature: Student ID Number: There are 12 multiple choice problems (4 points each) on this exam. Record the answers to the multiple choice questions on THIS PAGE.
More informationacetaldehyde (ethanal)
hem 263 Nov 2, 2010 Preparation of Ketones and Aldehydes from Alkenes zonolysis 1. 3 2. Zn acetone 1. 3 2. Zn acetone acetaldehyde (ethanal) Mechanism: 3 3 3 + - oncerted reaction 3 3 3 + ozonide (explosive)
More informationCHEMISTRY Topic #8: Oxidation and Reduction Reactions Fall 2018 Dr. Susan Findlay
CEMISTRY 2600 Topic #8: xidation and Reduction Reactions Fall 2018 Dr. Susan Findlay xidation States of Carbon Carbon can have any oxidation state from -4 (C 4 ) to +4 (C 2 ). As a general rule, increasing
More informationChapter 7: Alcohols, Phenols and Thiols
Chapter 7: Alcohols, Phenols and Thiols 45 -Alcohols have the general formula R-OH and are characterized by the presence of a hydroxyl group, -OH. -Phenols have a hydroxyl group attached directly to an
More informationCape Cod Community College
Cape Cod Community College Departmental Syllabus Prepared by the Department of Natural Sciences & Applied Technology Date of Departmental Approval: February 3, 2014 Date Approved by Curriculum and Programs:
More informationChapter 17 Aldehydes and Ketones
hapter 17 Aldehydes and Ketones arbonyl Groups polarized (1) Aldehydes and Ketones ' aldehydes ketones : and : are poor leaving groups (2) arboxylic Acid Derivatives l ' ' 2 carboxylic acid substituent
More informationBackground 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
More informationChapter 19. Synthesis and Reactions of b-dicarbonyl Compounds: More Chemistry of Enolate Anions. ß-dicarbonyl compounds. Why are ß-dicarbonyls useful?
Chapter 19 Synthesis and Reactions of b-dicarbonyl Compounds: More Chemistry of Enolate Anions ß-dicarbonyl compounds Two carbonyl groups separated by a carbon Three common types ß-diketone ß-ketoester
More informationChem 263 March 28, 2006
Chem 263 March 28, 2006 Properties of Carboxylic Acids Since carboxylic acids are structurally related to both ketones and aldehydes, we would expect to see some similar structural properties. The carbonyl
More informationALCOHOLS AND PHENOLS; ETHERS AND EPOXIDES; THIOLS AND SULFIDES
ALCOHOLS AND PHENOLS; ETHERS AND EPOXIDES; THIOLS AND SULFIDES A STUDENT SHOULD BE ABLE TO: 1. Give the IUPAC name when given the structure, and draw the structure given the name of open-chain and monocyclic
More informationChem 263 Nov 7, elimination reaction. There are many reagents that can be used for this reaction. Only three are given in this course:
hem 263 Nov 7, 2013 Preparation of Ketones and Aldehydes from Alcohols xidation of Alcohols [] must have at least 1 E elimination reaction [] = oxidation; removal of electrons [] = reduction; addition
More informationO C. Aldehyde: O C H 3 CH 2 C H propanal propionaldehyde. O C H 3 CH 2 C CH 2 CH 3 3-pentanone diethylketone
Aldehydes and Ketones Both contain the functional group Aldehyde: R Ketone R R' Aldehydes omenclature. IUPA: drop the 'e' from the name of the alkane and add 'al'. There are also common names which are
More informationChapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds
Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds Introduction Several functional groups contain the carbonyl group Carbonyl groups can be converted into alcohols
More informationMechanisms. . CCl2 F + Cl.
Mechanisms 1) Free radical substitution Alkane à halogenoalkane Initiation: Propagation: Termination: Overall: 2) Ozone depletion UV light breaks the C Cl bond releasing chlorine radical CFCl 3 F à. CCl2
More informationChem Final Examination August 7, 2004
Chem 281 2004-2 Final Examination August 7, 2004 Name: Student Number: Note: You are allowed to use models for this exam. Notes, textbooks and calculators are strictly prohibited. Write your final answers
More informationChemistry 210 Organic Chemistry I Summer Semester 1999 Dr. Somnath Sarkar
Chemistry 210 rganic Chemistry I Summer Semester 1999 Dr. Somnath Sarkar Final Examination Name: Thursday, July 29, 1999, 6:30 8:30 Question 1 Stereochemistry(MC#1) 16 Question 2. Substitution(MC #2) 16
More informationAlkylamines are compounds of the type shown, where R, R, and R are alkyl groups. One or more of these groups is an aryl group in arylamines.
22.20 Summary 955 22.20 SUMMARY Section 22.1 Alkylamines are compounds of the type shown, where R, R, and R are alkyl groups. ne or more of these groups is an aryl group in s. R R R R amine R Secondary
More information