Chapter 9 Alkynes. Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

Size: px
Start display at page:

Download "Chapter 9 Alkynes. Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display."

Transcription

1 Chapter 9 Alkynes Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

2 9.1 Sources of Alkynes

3 Acetylene Industrial preparation of acetylene is by dehydrogenation of ethylene. CH 3 CH C H 2 C CH 2 + H C H 2 C CH 2 HC CH + H 2 Cost of energy makes acetylene a more expensive industrial chemical than ethylene.

4 Naturally Occurring Alkynes Some alkynes occur naturally. For example, CH 3 (CH 2 ) 10 C O C(CH 2 ) 4 COH Tariric acid: occurs in seed of a Guatemalan plant.

5 Naturally Occurring Alkynes Some alkynes occur naturally. For example, Histrionicotoxin: defensive toxin in the poison dart frogs of Central and South America

6 9.2 Nomenclature

7 Nomenclature Acetylene and ethyne are both acceptable IUPAC names for HC CH Higher alkynes are named in much the same way as alkenes except using an -yne suffix instead of -ene. HC CCH 3 Propyne HC CCH 2 CH 3 1-Butyne or But-1-yne (CH 3 ) 3 CC CCH 3 4,4-Dimethyl-2-pentyne or 4,4-Dimethyl-pent-2-yne

8 9.3 Physical Properties of Alkynes The physical properties of alkynes are similar to those of alkanes and alkenes.

9 9.4 Structure and Bonding in Alkynes: sp Hybridization

10 Structure Linear geometry for acetylene 120 pm H C C H 106 pm 106 pm 121 pm CH 3 C C H 146 pm 106 pm

11 Cycloalkynes Cyclononyne is the smallest cycloalkyne stable enough to be stored at room temperature for a reasonable length of time. Cyclooctyne polymerizes on standing. C C

12 sp Hybridization in Acetylene Mix together (hybridize) the 2s orbital and one of the three 2p orbitals. 2p 2p 2sp 2s

13 sp Hybridization in Acetylene Mix together (hybridize) the 2s orbital and one of the three 2p orbitals. 2p Each carbon has two half-filled sp orbitals available to form σ bonds. 2sp

14 σ Bonds in Acetylene Each carbon is connected to a hydrogen by a σ bond. The two carbons are connected to each other by a σ bond and two π bonds. Figure 9.2 (a)

15 π Bonds in Acetylene One of the two π bonds in acetylene is shown here. The second π bond is at right angles to the first. Figure 9.2 (b)

16 π Bonds in Acetylene This is the second of the two π bonds in acetylene. Figure 9.2 (c)

17 Figure 9.3 Electrostatic Potential in Acetylene The region of highest negative charge lies above and below the molecular plane in ethylene. The region of highest negative charge encircles the molecule around its center in acetylene.

18 Table 9.1 Structural Features of Ethane, Ethylene, and Acetylene Ethane Ethylene Acetylene C C distance 153 pm 134 pm 120 pm C H distance 111 pm 110 pm 106 pm H C C angles C C BDE 368 kj/mol 611 kj/mol 820 kj/mol C H BDE 410 kj/mol 452 kj/mol 536 kj/mol hybridization of C sp 3 sp 2 sp % s character 25% 33% 50% pk a

19 9.5 Acidity of Acetylene and Terminal Alkynes H C C Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

20 Acidity of Hydrocarbons In general, hydrocarbons are exceedingly weak acids, but alkynes are not nearly as weak as alkanes or alkenes. Compound pk a HC CH 26 H 2 C CH 2 45 CH 4 60

21 Carbon: Hybridization and Electronegativity pk a = 62 C H H + + C : sp 3 H pk a = 45 : C H + + sp C C C 2 pk a = 26 C C H H + + C C : sp Electrons in an orbital with more s character are closer to the nucleus and more strongly held.

22 Sodium Acetylide Objective: Prepare a solution containing sodium acetylide NaC CH Will treatment of acetylene with NaOH be effective? NaOH + HC CH NaC CH + H 2 O

23 Sodium Acetylide No. Hydroxide is not a strong enough base to deprotonate acetylene... HO.. :.. + H C CH HO.. H + : C CH weaker acid pk a = 26 stronger acid pk a = 15.7 In acid-base reactions, the equilibrium lies to the side of the weaker acid.

24 Solution: Use a stronger base. Sodium amide is a stronger base than sodium hydroxide. NaNH 2 + HC CH NaC CH + NH H 2 N : + H C CH H H + : C 2 N CH stronger acid pk a = 26 Sodium Acetylide weaker acid pk a = 36 Ammonia is a weaker acid than acetylene. The position of equilibrium lies to the right.

25 9.6 Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes

26 Preparation of Alkynes There are two main methods for the preparation of alkynes: Carbon-carbon bond formation alkylation of acetylene and terminal alkynes Functional-group transformations elimination

27 Alkylation of Acetylene and Terminal Alkynes H C C H R C C H R C C R

28 Alkylation of Acetylene and Terminal Alkynes H C C: + R X S N 2 H C C R + : X The alkylating agent is an alkyl halide, and the reaction is nucleophilic substitution. The nucleophile is sodium acetylide or the sodium salt of a terminal (monosubstituted) alkyne.

29 Example: Alkylation of Acetylene HC CH NaNH 2 NH 3 HC CNa CH 3 CH 2 CH 2 CH 2 Br HC C CH 2 CH 2 CH 2 CH 3 (70-77%)

30 Example: Alkylation of a Terminal Alkyne (CH 3 ) 2 CHCH 2 C CH NaNH 2, NH 3 (CH 3 ) 2 CHCH 2 C CNa CH 3 Br (CH 3 ) 2 CHCH 2 C (81%) C CH 3

31 Example: Dialkylation of Acetylene H C C H 1. NaNH 2, NH 3 2. CH 3 CH 2 Br CH 3 CH 2 C C H 1. NaNH 2, NH 3 2. CH 3 Br CH 3 CH 2 C C CH 3 (81%)

32 Limitation Effective only with primary alkyl halides Secondary and tertiary alkyl halides undergo elimination

33 Acetylide Ion as a Base E2 predominates over S N 2 when alkyl halide is secondary or tertiary. H C C: H C E2 C X H C C H + C C + : X

34 9.7 Preparation of Alkynes by Elimination Reactions

35 Preparation of Alkynes by Double Dehydrohalogenation H X H H C C C C H X X X Geminal dihalide Vicinal dihalide The most frequent applications are in preparation of terminal alkynes.

36 Geminal dihalide Alkyne (CH 3 ) 3 CCH 2 CHCl NaNH 2, NH 3 2. H 2 O (CH 3 ) 3 CC CH (56-60%)

37 Geminal dihalide Alkyne (CH 3 ) 3 CCH 2 CHCl 2 (CH 3 ) 3 CCH CHCl (CH 3 ) 3 CC CH NaNH 2, NH 3 NaNH 2, NH 3 (slow) (slow) H 2 O (CH 3 ) 3 CC CNa NaNH 2, NH 3 (fast)

38 Vicinal dihalide Alkyne CH 3 (CH 2 ) 7 CH CH 2 Br Br 1. 3NaNH 2, NH 3 2. H 2 O CH 3 (CH 2 ) 7 C CH (54%)

39 9.8 Reactions of Alkynes Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

40 Reactions of Alkynes Acidity (Section 9.5) Hydrogenation (Section 9.9) Metal-Ammonia Reduction (Section 9.10) Addition of Hydrogen Halides (Section 9.11) Hydration (Section 9.12) Addition of Halogens (Section 9.13) Ozonolysis (Section 9.14)

41 9.9 Hydrogenation of Alkynes

42 Hydrogenation of Alkynes RC CR' + 2H 2 cat RCH 2 CH 2 R' catalyst = Pt, Pd, Ni, or Rh Alkene is an intermediate.

43 Heats of Hydrogenation CH 3 CH 2 C CH CH 3 C CCH kj/mol 275 kj/mol Alkyl groups stabilize triple bonds in the same way that they stabilize double bonds. Internal triple bonds are more stable than terminal ones.

44 Partial Hydrogenation RC CR' H 2 RCH CHR' cat H 2 cat RCH 2 CH 2 R' Alkynes could be used to prepare alkenes if a catalyst were available that is active enough to catalyze the hydrogenation of alkynes, but not active enough for the hydrogenation of alkenes.

45 Lindlar Catalyst RC CR' H 2 RCH CHR' cat H 2 cat There is a catalyst that will catalyze the hydrogenation of alkynes to alkenes, but not that of alkenes to alkanes. It is called the Lindlar catalyst and consists of palladium supported on CaCO 3, which has been poisoned with lead acetate and quinoline. RCH 2 CH 2 R' syn-hydrogenation occurs; cis alkenes are formed.

46 Example CH 3 (CH 2 ) 3 C C(CH 2 ) 3 CH 3 + H 2 Lindlar Pd CH 3 (CH 2 ) 3 (CH 2 ) 3 CH 3 C C H (87%) H

47 9.10 Metal-Ammonia Reduction of Alkynes Alkynes trans-alkenes

48 Partial Reduction RC CR' RCH CHR' RCH 2 CH 2 R' Another way to convert alkynes to alkenes is by reduction with sodium (or lithium or potassium) in ammonia. trans-alkenes are formed.

49 Example CH 3 CH 2 C CCH 2 CH 3 Na, NH 3 CH 3 CH 2 H C C H (82%) CH 2 CH 3

50 Mechanism Metal (Li, Na, K) is reducing agent; H 2 is not involved Four steps (1) electron transfer (2) proton transfer (3) electron transfer (4) proton transfer

51 Mechanism Step (1): Transfer of an electron from the metal to the alkyne to give an anion radical. R M + C C R' + M. R Ċ.. C R'

52 Mechanism Step (2): Transfer of a proton from the solvent (liquid ammonia) to the anion radical. R. C.. C R' R C. C R'.. H NH 2 H.. : NH 2

53 Mechanism Step (3): Transfer of an electron from the metal to the alkenyl radical to give a carbanion. R C. C R' + M. R C M +.. C H H R'

54 Mechanism Step (4): Transfer of a proton from the solvent (liquid ammonia) to the carbanion. R C.. C.. H NH 2.. R H : NH 2 C C H R' H R'

55 Suggest efficient syntheses of (E)- and (Z)-2- heptene from propyne and any necessary organic or inorganic reagents.

56 Strategy

57 Synthesis 1. NaNH 2 2. CH 3 CH 2 CH 2 CH 2 Br H 2, Lindlar Pd Na, NH 3

58 9.11 Addition of Hydrogen Halides to Alkynes

59 Follows Markovnikov's Rule CH 3 (CH 2 ) 3 C CH HBr CH 3 (CH 2 ) 3 C CH 2 Br (60%) Alkynes are slightly less reactive than alkenes.

60 Termolecular Rate-determining Step.. H Br :.. RC CH.. H Br :.. Observed rate law: rate = k[alkyne][hx] 2

61 Two Molar Equivalents of Hydrogen Halide CH 3 CH 2 C CCH 2 CH 3 2 HF H F CH 3 CH 2 C C CH 2 CH 3 H F (76%)

62 Free-radical Addition of HBr CH 3 (CH 2 ) 3 C CH HBr peroxides CH 3 (CH 2 ) 3 CH CHBr (79%) regioselectivity opposite to Markovnikov's rule

63 9.12 Hydration of Alkynes

64 Hydration of Alkynes expected reaction: RC CR' + H 2 O H + RCH CR' observed reaction: RC CR' + H 2 O H + OH enol RCH 2 CR' O ketone

65 Enols RCH CR' RCH 2 CR' enol OH O ketone Enols are tautomers of ketones, and exist in equilibrium with them. Keto-enol equilibration is rapid in acidic media. Ketones are more stable than enols and predominate at equilibrium.

66 Mechanism of Conversion of Enol to Ketone H + : O H H C.. : O C H

67 Mechanism of Conversion of Enol to Ketone.. : O H H : O: H C C + H

68 Mechanism of Conversion of Enol to Ketone H H C.. : O C + H : O: H

69 Mechanism of Conversion of Enol to Ketone H H C.. : O C H + O: H

70 Key Carbocation Intermediate Carbocation is stabilized by electron delocalization (resonance)... : O H +.. O H H C C + H C C

71 Example of Alkyne Hydration CH 3 (CH 2 ) 2 C C(CH 2 ) 2 CH 3 H 2 O, H + Hg 2+ via OH O CH 3 (CH 2 ) 2 CH C(CH 2 ) 2 CH 3 CH 3 (CH 2 ) 2 CH 2 C(CH 2 ) 2 CH 3 (89%)

72 Regioselectivity Markovnikov's rule followed in formation of enol O CH 3 (CH 2 ) 5 C CH H 2 O, H 2 SO 4 CH 3 (CH 2 ) 5 CCH 3 HgSO 4 (91%) via OH CH 3 (CH 2 ) 5 C CH 2

73 9.13 Addition of Halogens to Alkynes

74 Example HC CCH 3 + 2Cl 2 Cl Cl 2 CH C CH 3 Cl (63%)

75 Addition is anti CH 3 CH 2 Br 2 CH 3 CH 2 C CCH 2 CH 3 C C Br Br CH 2 CH 3 (90%)

76 9.14 Ozonolysis of Alkynes gives two carboxylic acids by cleavage of triple bond

77 Example CH 3 (CH 2 ) 3 C CH 1. O 3 2. H 2 O O CH 3 (CH 2 ) 3 COH (51%) + O HOCOH

Chem 145 Unsaturated hydrocarbons Alkynes

Chem 145 Unsaturated hydrocarbons Alkynes Dr. Seham ALTERARY Chem 145 Unsaturated hydrocarbons Alkynes Chapter 4 1434-1435 2013-2014 2 st semester By the end of this chapter you should be familiar with: Definition for Alkynes. Nomenclature of

More information

sp 2 geometry tetrahedral trigonal planar linear ΔH C-C ΔH C-H % s character pk a 464 KJ/mol 33% 44

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

More information

C h a p t e r T e n : Alkynes. Tazarotene, a synthetic acetylenic retinoid used to treat acne

C h a p t e r T e n : Alkynes. Tazarotene, a synthetic acetylenic retinoid used to treat acne C h a p t e r T e n : Alkynes N S Tazarotene, a synthetic acetylenic retinoid used to treat acne CHM 321: Summary of Important Concepts YConcepts for Chapter 10: Alkynes I. Structure and bonding A. sp-hybridization

More information

Organic Chemistry. M. R. Naimi-Jamal. Faculty of Chemistry Iran University of Science & Technology

Organic Chemistry. M. R. Naimi-Jamal. Faculty of Chemistry Iran University of Science & Technology Organic Chemistry M. R. Naimi-Jamal Faculty of Chemistry Iran University of Science & Technology Chapter 4-3: Continue Alkynes: An Introduction to Organic Synthesis Based on: McMurry s Organic Chemistry,

More information

Lecture 20 Organic Chemistry 1

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

More information

Organic Chemistry. Alkynes

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

More information

Chapter 8: Chemistry of Alkynes (C n H 2n-2 )

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:

More information

Chapter 9 Alkynes. Introduction

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

More information

به نام خدا. Organic Chemistry 1. Dr Morteza Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran

به نام خدا. Organic Chemistry 1. Dr Morteza Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran به نام خدا 8 Organic Chemistry 1 Dr Morteza Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir 8 Alkynes: An Introduction to Organic Synthesis آلکین ها: مقدمه ای

More information

This reactivity makes alkenes an important class of organic compounds because they can be used to synthesize a wide variety of other compounds.

This reactivity makes alkenes an important class of organic compounds because they can be used to synthesize a wide variety of other compounds. This reactivity makes alkenes an important class of organic compounds because they can be used to synthesize a wide variety of other compounds. Mechanism for the addition of a hydrogen halide What happens

More information

Alkynes Nomenclature of Alkynes

Alkynes Nomenclature of Alkynes Chapter 7 Alkynes Alkynes - hydrocarbons containing a carbon-carbon triple bond (2 bonds) Acyclic alkanes = C n H 2n+2 Alkenes and cyclic alkanes = C n H 2n Alkynes (and cyclic alkenes) = C n H 2n-2 The

More information

Alkynes. Alkynes-hydrocarbons with a carbon-carbon triple bond.

Alkynes. Alkynes-hydrocarbons with a carbon-carbon triple bond. Alkynes Alkynes-hydrocarbons with a carbon-carbon triple bond. The carbon-carbon triple bond results from the interaction of two sp hybridized carbon atoms. 180 degree angle. Linear. The carbon-carbon

More information

REACTION AND SYNTHESIS REVIEW

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

More information

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

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

More information

Chapter 7 - Alkenes and Alkynes I

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

More information

Chapter 19: Alkenes and Alkynes

Chapter 19: Alkenes and Alkynes Chapter 19: Alkenes and Alkynes The vast majority of chemical compounds that we know anything about and that we synthesize in the lab or the industrial plant are organic compounds. The simplest organic

More information

ST. JOSEPH S COLLEGE OF ARTS & SCIENCE (AUTONOMOUS) ST. JOSEPH S COLLEGE ROAD, CUDDALORE CH101T ORGANIC CHEMISTRY I (SEMESTER-I)

ST. JOSEPH S COLLEGE OF ARTS & SCIENCE (AUTONOMOUS) ST. JOSEPH S COLLEGE ROAD, CUDDALORE CH101T ORGANIC CHEMISTRY I (SEMESTER-I) UNIT I 1. The hybridization involved in the formation of acetylene is a) sp b) sp 2 c) sp 3 d) sp 3 d 2. The IUPAC name of is 1. 3-hexene b) 4-hexene c) 3-hexyne d) 4-hexyne 3. -------- is the type of

More information

Chapter 8 Alkyl Halides and Elimination Reactions

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

More information

11/5/ Conjugated Dienes. Conjugated Dienes. Conjugated Dienes. Heats of Hydrogenation

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

More information

Alkynes Are Found in Natural Products

Alkynes Are Found in Natural Products Objective 13 Apply Reactivity Principles to Electrophilic Addition Reactions 2: Alkynes Identify structural features (pi bond) and electrophiles Use curved arrows to predict product Alkynes Are Found in

More information

Chapter 3 Alkenes and Alkynes. Excluded sections 3.15&3.16

Chapter 3 Alkenes and Alkynes. Excluded sections 3.15&3.16 Chapter 3 Alkenes and Alkynes Excluded sections 3.15&3.16 3.1 Definition and Classification Alkene: a hydrocarbon that contains one or more carboncarbon double bonds. ethylene is the simplest alkene. Alkyne:

More information

CHAPTER 3 ALKENES, ALKYNES & CONJUGATE DIENES

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

More information

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

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

More information

ORGANIC CHEMISTRY- 1

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.

More information

Chapter 3. Alkenes And Alkynes

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

More information

CHEM 3013 ORGANIC CHEMISTRY I LECTURE NOTES CHAPTER 8

CHEM 3013 ORGANIC CHEMISTRY I LECTURE NOTES CHAPTER 8 EM 3013 GANI EMISTY I LETUE NTES 1 1. The Alkyne Functional Group APTE 8 Alkynes are compounds with carbon-carbon triple bonds. ecall that alkanes use sp 3 hybrid orbitals and that alkenes use sp 2 hybrid

More information

1/4/2011. Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds

1/4/2011. 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 information

Just Chemistry Department Organic Chemistry 217

Just Chemistry Department Organic Chemistry 217 Part 2 Just Chemistry Department Organic Chemistry 217 Chapter 3 Alkenes And Alkynes كيمياء عضوية ك 217 د. حسين المغيض Dr. Hussein Al-Mughaid Direct hydration: Addition of H 2 O (Acid-catalyzed hydration)

More information

212 LSW ALKYNES S04. Alkynes

212 LSW ALKYNES S04. Alkynes Alkynes Doubly unsaturated functional group Terminal alkynes, R-- 1) 2) 3) 4) Nomenclature: Functional group suffix = Disubstituted alkynes, R--R' Monosubstituted alkynes, R-- Stability: Substituted alkynes

More information

OCH 3. 3-butyn-2-ol 3-hydroxy-1-butyne

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

More information

Learning Guide for Chapter 13 - Alkynes

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

More information

DAV CENTENARY PUBLIC SCHOOL, PASCHIM ENCLAVE, NEW DELHI - 87

DAV CENTENARY PUBLIC SCHOOL, PASCHIM ENCLAVE, NEW DELHI - 87 HYDROCARBONS 1. Why do alkenes prefer to undergo electrophilic addition reaction while arenes prefer electrophilic substitution reactions? Explain. 2. Alkynes on reduction with sodium in liquid ammonia

More information

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

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

More information

Detailed Course Content

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

More information

Chemistry 210 Organic Chemistry I Fall Semester 2000 Dr. Rainer Glaser

Chemistry 210 Organic Chemistry I Fall Semester 2000 Dr. Rainer Glaser Chemistry 210 Organic Chemistry I Fall Semester 2000 Dr. Rainer Glaser Examination #3 Alkenes and Alkynes. Structure, Synthesis and Reactions. Friday, November 17, 2000, 9:00-9:50 Name: Question 1. Alkenes

More information

Chapter 12: Unsaturated Hydrocarbons

Chapter 12: Unsaturated Hydrocarbons Chapter 12: Unsaturated Hydrocarbons UNSATURATED HYDROCARBONS contain carbon-carbon multiple bonds. Alkenes C=C double bonds Alkynes triple bonds Aromatics benzene rings 1 2 NAMING ALKENES Step 1: Name

More information

Chapter 13 Alkenes and Alkynes & Aromatic Compounds

Chapter 13 Alkenes and Alkynes & Aromatic Compounds Chapter 13 Alkenes and Alkynes & Aromatic Compounds Chapter Outline 13.1 Alkenes and Alkynes 13.2 Nomenclature of Alkenes and Alkynes 13.3 Cis Trans Isomers 13.4 Alkenes in Food and Medicine 13.6 Reactions

More information

CHE1502. Tutorial letter 203/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry

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

More information

Chapter 5. Reactions of Alkenes and Alkynes

Chapter 5. Reactions of Alkenes and Alkynes Learning objectives: Chapter 5. Reactions of Alkenes and Alkynes 1. Differentiate primary, secondary, and tertiary carbocations, and recognize the order of stability for these carbocations. 2. Identify

More information

Class XI Chapter 13 Hydrocarbons Chemistry

Class XI Chapter 13 Hydrocarbons Chemistry Question 13.1: How do you account for the formation of ethane during chlorination of methane? Chlorination of methane proceeds via a free radical chain mechanism. The whole reaction takes place in the

More information

Chem 251 Fall Learning Objectives

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

More information

I. Multiple Choice Questions (Type-I)

I. Multiple Choice Questions (Type-I) Unit 13 HYDROCARBONS I. Multiple Choice Questions (Type-I) 1. Arrange the following in decreasing order of their boiling points. (A) n butane (B) 2 methylbutane (C) n-pentane (D) 2,2 dimethylpropane A

More information

ALCOHOLS AND PHENOLS

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

More information

350 Organic Chemistry I Winona State University

350 Organic Chemistry I Winona State University 350 Organic Chemistry I Winona State University Exam #4B, December 9, 2013 Professor T. Nalli Name General Instructions: Write your name in the space provided above and on the provided Scan-tron form.

More information

Organic Chemistry Lecture 2 - Hydrocarbons, Alcohols, Substitutions

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

More information

1. What is the letter designation given to dumbbell shaped orbitals like the one depicted below?

1. What is the letter designation given to dumbbell shaped orbitals like the one depicted below? 1. What is the letter designation given to dumbbell shaped orbitals like the one depicted below? 2. Which of the following does not have an octet of electrons surrounding the central atom? A. B 3 B. C

More information

Chapter 8 - Alkenes and Alkynes II Addition Reactions of Alkenes - Electrons in the π bond of alkenes react with electrophiles

Chapter 8 - Alkenes and Alkynes II Addition Reactions of Alkenes - Electrons in the π bond of alkenes react with electrophiles Andrew Rosen Chapter 8 - Alkenes and Alkynes II 8.1 - Addition Reactions of Alkenes - Electrons in the π bond of alkenes react with electrophiles 8.2 - Electrophilic Addition of Hydrogen Halides to Alkenes:

More information

Additions to the Carbonyl Groups

Additions 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 information

Chapter 1 Reactions of Organic Compounds. Reactions Involving Hydrocarbons

Chapter 1 Reactions of Organic Compounds. Reactions Involving Hydrocarbons Chapter 1 Reactions of Organic Compounds Reactions Involving Hydrocarbons Reactions of Alkanes Single bonds (C-C) are strong and very hard to break, therefore these compounds are relatively unreactive

More information

1. Which statement is not true of nucleophillic substitution reactions?!

1. Which statement is not true of nucleophillic substitution reactions?! Mock Exam 3 CH 235-2F Ch. 7, 8, 9, and 11 Multiple Choice: 1. Which statement is not true of nucleophillic substitution reactions? a. SN1 proceeds through a cation intermediate. b. SN2 occurs with inversion

More information

CHEM 241 ALKYNES CHAP 9 ASSIGN

CHEM 241 ALKYNES CHAP 9 ASSIGN HEM 241 ALKYNES HAP 9 ASSIGN 1. What is the IUPA name of the following compound A. 5-propyl-3-heptyne B. 5-isopropyl-3-heptyne. 5-ethyl-3-octyne D. 4-ethyl-5-octyne 2. What is the correct IUPA name for

More information

Practice Multiple-Choice Questions for Ending Chem 21 and/or Starting Chem 22

Practice Multiple-Choice Questions for Ending Chem 21 and/or Starting Chem 22 Practice Multiple-Choice Questions for Ending Chem 21 and/or Starting Chem 22 Includes information from chapters 5-10 of the third edition of Klein s Organic Chemistry text. 1. Which of the following compounds

More information

Alkenes. Dr. Munther A. M-Ali For 1 st Stage Setudents

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

More information

CHAPTER HYDROCARBONS. Chapterwise Previous year Qs. (a) Na (b) HCl in H2O (c) KOH in C2H5OH (d) Zn in alcohol. Ans: (c)

CHAPTER HYDROCARBONS. Chapterwise Previous year Qs. (a) Na (b) HCl in H2O (c) KOH in C2H5OH (d) Zn in alcohol. Ans: (c) 122 CHAPTER HYDROCARBONS 1. Acetylenic hydrogens are acidic because [1989] Sigma electron density of C Hbond in acetylene is nearer to carbon, which has 50% s- character Acetylene has only open hydrogen

More information

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

But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens). Reactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. Normally: Oxidation

More information

ORGANIC - BROWN 8E CH ALKENES AND REACTIONS OF ALKENES

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

More information

When H and OH add to the alkyne, an enol is formed, which rearranges to form a carbonyl (C=O) group:

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

More information

(1) Recall the classification system for substituted alkenes. (2) Look at the alkene indicated. Count the number of bonds to non-hydrogen groups.

(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

More information

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

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

More information

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

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

More information

% % Important Concepts. Problems. Problems C h a p t e r

% % Important Concepts. Problems. Problems C h a p t e r Problems C h a p t e r 1 3 599 Important Concepts 1. The rules for naming alkynes are essentially the same as those formulated for alkenes. Molecules with both double and triple bonds are called alkenynes,

More information

Classes of Alkenes. Alkenes and Alkynes. Saturated compounds (alkanes): Have the maximum number of hydrogen atoms attached to each carbon atom.

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

More information

Organic Chemistry I: Reactions and Overview

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

More information

Química Orgânica I. alkynes 2008/09. w3.ualg.pt\~abrigas QOI 0809 ALKYNE 1. w3.ualg.pt\~abrigas QOI 0809 ALKYNE 2

Química Orgânica I. alkynes 2008/09. w3.ualg.pt\~abrigas QOI 0809 ALKYNE 1. w3.ualg.pt\~abrigas QOI 0809 ALKYNE 2 Química Orgânica I 2008/09 w3.ualg.pt\~abrigas QOI 0809 ALKYNE 1 alkynes w3.ualg.pt\~abrigas QOI 0809 ALKYNE 2 1 Name these: 3 propyne 3 2 2 Br 5-bromo-2-pentyne 5-bromopent-2-yne 3 3 3 2 3 2,6-dimethyl-3-heptyne

More information

Learning Guide for Chapter 11 - Alkenes I

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

More information

Chapter 13 Alkenes and Alkynes Based on Material Prepared by Andrea D. Leonard University of Louisiana at Lafayette

Chapter 13 Alkenes and Alkynes Based on Material Prepared by Andrea D. Leonard University of Louisiana at Lafayette Chapter 13 Alkenes and Alkynes Based on Material Prepared by Andrea D. Leonard University of Louisiana at Lafayette 1 Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

More information

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

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

More information

ORGANIC - BROWN 8E CH ALDEHYDES AND KETONES.

ORGANIC - BROWN 8E CH ALDEHYDES AND KETONES. !! 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 information

CHAPTER 9. ALKYNES: AN INTRODUCTION TO ORGANIC SYNTHESIS

CHAPTER 9. ALKYNES: AN INTRODUCTION TO ORGANIC SYNTHESIS CAPTER 9. ALKYNES: AN INTRDUCTIN T RGANIC SYNTESIS Alkyne Nomenclature. Like alkenes, number so the alkyne gets the lowest number. Name the following two molecules: 3 C C CC 2 C 2 C(C 3 ) 2 Cl If, however,

More information

Allyl radicals are especially stable due to resonance ( and double bond switch places):

Allyl radicals are especially stable due to resonance ( and double bond switch places): Ch 10 Alkyl Halides Nomenclature Rules The parent is the longest alkyl chain or ring. The #1 C for a chain is at the end that is nearest to the first substituent. The #1 C for a ring possesses the first

More information

Open chain saturated hydrocarbon with general formula (CnH2n+2).

Open chain saturated hydrocarbon with general formula (CnH2n+2). Compounds of carbon and hydrogen. Classification of Hydrocarbons: Alkane Open chain saturated hydrocarbon with general formula (CnH2n+2). All the C atoms are single bonded i.e. sp 3 hybridised. Conformations

More information

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 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

More information

HONORS ORGANIC CHEM. HAHS MRS. RICHARDS

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

More information

ELECTROPHILIC ADDITIONS OF ALKENES AS THE COUNTERPART OF ELIMINATIONS

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

More information

nsaturated Hydrocarbons: Alkenes, Cycloalkenes and Dienes

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

More information

Synthesis 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. 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 information

2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2- methylcyclohexene?

2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2- methylcyclohexene? Quiz 7.1 Alkene Additions and Hydrohalogenations 1. Which is the most stable carbocation? 2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2- methylcyclohexene? 3. What

More information

Reactions of Alkenes and Alkynes

Reactions of Alkenes and Alkynes 5 2 2 2 2 2 2 2 Reactions of Alkenes and Alkynes APTER SUMMARY Addition is the characteristic reaction of alkenes and alkynes. Since the carbons of a double or triple bond do not have the maximum number

More information

Introduction to Alkenes and Alkynes

Introduction to Alkenes and Alkynes Introduction to Alkenes and Alkynes In an alkane, all covalent bonds between carbon were σ (σ bonds are defined as bonds where the electron density is symmetric about the internuclear axis) In an alkene,

More information

DAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction

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

More information

Structure and Preparation of Alkenes: Elimination Reactions

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

More information

Chemistry 210 Organic Chemistry I Winter Semester 2001 Dr. Rainer Glaser

Chemistry 210 Organic Chemistry I Winter Semester 2001 Dr. Rainer Glaser hemistry 210 rganic hemistry I Winter Semester 2001 Dr. Rainer Glaser Examination #3 Alkenes and Alkynes. Structure, Synthesis and Reactions. Friday, April 20, 2001, 9:00-9:50 Name: Answer Key Question

More information

ADDITION REACTIONS OF ALKYNES

ADDITION REACTIONS OF ALKYNES ADDITIN REATINS F ALKYNES ADDITIN REATINS F ALKYNES two pi bonds A carbon-carbon triple bond is like two carbon-carbon double bonds. Most double bond reagents will react twice. ALKYNES ARE LESS REATIVE

More information

Chapter 6: Organic Halogen Compounds; Substitution and Elimination Reactions

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

More information

enol unstable; can't be isolated

enol unstable; can't be isolated Name 1 ke alkenes, alkynes are stabilized by alkyl groups, so internal alkynes (i.e. disubstituted alkynes) are generally more stable than terminal alkynes (i.e. monosubstituted alkynes). With this in

More information

Alkenes - Addition Reactions

Alkenes - Addition Reactions Alkenes - Addition Reactions Alkenes- reactions. Addition Ionic Free radical Reduction Oxidation Substitution Reactions, alkenes: 1. Addition of hydrogen (reduction). 2. Addition of halogens. 3. Addition

More information

Preparation of alkenes

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

More information

Alcohol Synthesis. Dr. Sapna Gupta

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

More information

Ethers can be symmetrical or not:

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

More information

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

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

More information

Chapter 8. Acidity, Basicity and pk a

Chapter 8. Acidity, Basicity and pk a Chapter 8 Acidity, Basicity and pk a p182 In this reaction water is acting as a base, according to our definition above, by accepting a proton from HCl which in turn is acting as an acid by donating a

More information

Chapter 7. Alkenes: Reactions and Synthesis

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

More information

Carbonyl Chemistry V + C O C. Chemistry /30/02

Carbonyl Chemistry V + C O C. Chemistry /30/02 arbonyl hemistry V Ō - + Keto-enol enol Tautomerism H 3 H 3 Ketone H H R 2 H R' H H 3 H 2 H Enol H Acid atalyzed α Halogenation R 2 R' + X 2 H + R 2 R' + HX H X X 2 can be l 2, Br 2, or I 2. Substitution

More information

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

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

More information

Chapter 20: Carboxylic Acids and Nitriles شیمی آلی 2

Chapter 20: Carboxylic Acids and Nitriles شیمی آلی 2 Chapter 20: Carboxylic Acids and Nitriles شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic Chemistry, 7 th edition The

More information

Chapter 13: Alcohols and Phenols

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

More information

Organic Chemistry SL IB CHEMISTRY SL

Organic Chemistry SL IB CHEMISTRY SL Organic Chemistry SL IB CHEMISTRY SL 10.1 Fundamentals of organic chemistry Understandings: A homologous series is a series of compounds of the same family, with the same general formula, which differ

More information

Chapter 9 Aldehydes and Ketones

Chapter 9 Aldehydes and Ketones Chapter 9 Aldehydes and Ketones 9.1 Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al The aldehyde functional group is always carbon

More information

ORGANIC REACTIONS 11 MARCH 2014

ORGANIC REACTIONS 11 MARCH 2014 ORGANIC REACTIONS 11 MARCH 2014 In this lesson we: Lesson Description Look at the chemical reactions of organic molecules Summary Organic molecules can undergo several important chemical reactions. 1.

More information

Reducing Agents. Linda M. Sweeting 1998

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

More information