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

Slides:



Advertisements
Similar presentations
Hydroxy Compounds (Chapter 34). Hydroxy compounds Aliphatic Monohydric Alcohols 1 o Primary RCH 2 OH (one –R) 2 o Secondary R 2 CHOH (two –R) 3 o Tertiary.
Advertisements

Alkyl Halides Dr. Noha Elnagdi.
Substitution and Elimination Competing Reactions
Oxidation-Reduction & Organometallic
Elimination Reactions of Alkyl Halides
Alkyl Halides Organo halogen Alkyl halide Aryl halide Halide vynilik
Alkyl halides can react with Lewis bases by nucleophilic substitution and/or elimination. C CHX + Y : – C C Y H X : – + C C + H Y X : – +  -elimination.
Alkyl halides, Alcohols, Ethers, Thiols. Required background: Acidity and basicity Functional groups Molecular geometry and polarity Essential for: 1.
162 Chapter 19: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution 19.1: Nomenclature of Carboxylic Acid Derivatives (please read)
Advanced Higher Chemistry
Chapter 20 Carboxylic Acids and Nitriles
Carbon Nucleophiles : Organometallics of Li, Mg etc. 1. Cyanide :Well known 1 carbon unit 2. Acetylides :pKa = 25 Requires polar solvent to solubilize.
Introduction Structure of the Carbonyl Group
Chapter 8: Ethers and Epoxides Diethyl ether in starting fluid.
Organic Chemistry Chapter 10. Functional Groups The Key To Substitution Reactions The Leaving Group Goes.
17.2 How Aldehydes and Ketones React (Part I) 1 ++ R = alkyl or aryl (C) Y = alkyl, aryl or H (class II) (No leaving group) -- Electron rich (Lewis.
Alcohols: Structure & Synthesis
Organic Chemistry Chapter 8. Substitution and Elimination If an sp 3 C is bonded to electronegative atom Substitution reactions and Elimination reactions.
Chapter 8 - Nucleophilic Substitution at sp3 C
© Prentice Hall 2001Chapter 91 Substitution Reactions S N 1 mechanism: C–X bond breaks first without any help from nucleophile This is a two-step process.
Alkyl Halides R-X (X = F, Cl, Br, I)
_  +  Chapter 11 Reactions of Alcohols Organic Chemistry, 6 th Edition L. G. Wade, Jr.
165 Chapter 20: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution 20.1: Nomenclature of Carboxylic Acid Derivatives (please read)
H ALOGENOALKANES OR ALKYL HALIDES. S ITES : D Halogenalkanes+Sn1+Sn2.pdf Animation:
OrgChem- Chap20 1 Chapter 20 Enolates / Other Carbon Nucleophiles C-C bond formation is very important  larger, more complex organic molecule can be made.
Chemistry. Alkyl and Aryl halides–1 Session objectives 1.Classification 2.Nature of C — X bond 3.Preparation of alkyl halides 4.Physical and chemical.
Chapter 8 Nucleophilic Substitution (in depth) & Competing Elimination
Organic chemistry for medicine and biology students Chem 2311 Chapter 6 Alkylhalides (Substitution and Elimination) By Prof. Dr. Adel M. Awadallah Islamic.
Nucleophilic Substitution. Y : – RX Y R + : X – Nucleophile is a Lewis base (electron-pair donor), often negatively charged and used as Na + or K + salt.
Preparation and Reactions of Carboxylic Acids
CH 20: Carboxylic Acids and Nitriles Renee Y. Becker CHM 2211 Valencia Community College 1.
Increasing polarizability improves nucleophilic power.
Chapter 8 Nucleophilic Substitution
WWU -- Chemistry Chapter 10 Nucleophilic Substitution: The S N 1 and S N 2 Mechanisms.
Reactions of haloalkanes.. Nucleophilic substitution Halogens are relatively electronegative. So the carbon/halogen bond will be polarised. δ-δ- δ+δ+
8.13 Substitution and Elimination as Competing Reactions.
CHE 242 Unit V Structure and Reactions of Alcohols, Ethers and Epoxides; Basic Principles of NMR Spectroscopy CHAPTER ELEVEN Terrence P. Sherlock Burlington.
8.14 Sulfonate Esters as Substrates in Nucleophilic Substitution
Dr. Wolf's CHM 201 & Substitution And Elimination As Competing Reactions.
Chapter 8 I. Nucleophilic Substitution (in depth) II
1 FIVE METHODS OF PREPARING ALCOHOLS. 2 5 METHODS OF PREPARING ALCOHOLS 1. Hydroxide ions (OH - ) replace halogens in unhindered alkyl halides (Me° and.
Chapter 9: Elimination Reactions of Alkyl Halides: Competition between Substitutions and Eliminations.
Ethers and Thioethers 2.
Carboxylic Acids and Derivatives. Naming Carboxylic Acids Starting materials for acyl derivatives (esters, amides, and acid chlorides) Abundant in nature.
54c) Fill in the blanks f) j)
Organic Chemistry.
Carbonyl Alpha-Substitution Reactions
Halogenoalkanes AH Chemistry Unit 3(b). Background Also known as haloalkanes or alkyl halides Rare in the natural world Widely used Synthesised in the.
234 Chapter 24: Phenols. Chapter 24: Phenols. Alcohols contain an OH group bonded to an sp 3 -hybridized carbon. Phenols contain an OH group bonded to.
18.7 Salts of Carboxylic Acids Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
VIDEO EXAMPLE OF SUBSTITUTION The hydrolysis of t-butyl halides They’re often easy/fast (facile) Done at room.
CHAPTER 4 ALKYL HALIDE BY MAHWASH HAFEEZ. Alkyl Halides Alkyl halides have the general formula R-X R is alkyl group (functional group) and X is the halogen.
Substitution Reactions of Alcohols We have looked at substitution reactions that take place via two mechanisms: S N 1 - works for substrates that can form.
19.6 Substituents and Acid Strength. standard of comparison is acetic acid (X = H) Substituent Effects on Acidity X CH 2 COH O K a = 1.8 x pK a.
16.4 Crown Ethers Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Generalized Polar Reactions An electrophile, an electron-poor species, combines with a nucleophile, an electron-rich species An electrophile is a Lewis.
Carboxylic acids and Their Derivatives
Oxidation-Reduction & Organometallic
Sulfur analogs of alcohols, phenols and ethers
Substitution and Elimination Reactions of Alkyl Halides
Terrence P. Sherlock Burlington County College 2004
alkane alkene alkyne arene
8.13 Substitution and Elimination as Competing Reactions
Ethers The compounds that have the R – O – R group are know as ethers. The two R groups linked to oxygen can be different or the same and they also can.
Chapter 22 Carbonyl Alpha-Substitution Reactions
Chapter 8 - Nucleophilic Substitution at sp3 C
ALKYL HALIDES OR HALOALKANES
Substitution and Elimination Competing Reactions SN1 & SN2 vs
NUCLEOPHILIC SUBSTITUTION REACTIONS
Organic Chemistry II Chapter 22 Carbonyl Alpha-Substitution Reactions
Presentation transcript:

Chapter 8 Nucleophilic Substitution

8.1 Functional Group Transformation By Nucleophilic Substitution

Y : –RX Y R + + : X – nucleophile is a Lewis base (electron-pair donor) often negatively charged and used as Na + or K + salt substrate is usually an alkyl halide Nucleophilic Substitution

Substrate cannot be an a vinylic halide or an aryl halide, except under certain conditions to be discussed in Chapter 23. X CCX Nucleophilic Substitution

+RX gives an ether Alkoxide ion as the nucleophile.. O:O:O:O:.. R'– + : X R.. O..R' – Table 8.1 Examples of Nucleophilic Substitution

(CH 3 ) 2 CHCH 2 ONa + CH 3 CH 2 Br Isobutyl alcohol (CH 3 ) 2 CHCH 2 OCH 2 CH 3 + NaBr Ethyl isobutyl ether (66%) Example

+RX gives an ester Carboxylate ion as the nucleophile.. O:O:O:O:.. R'C – + : X R.. O.. R'C –O O Table 8.1 Examples of Nucleophilic Substitution

OK + CH 3 (CH 2 ) 16 C CH 3 CH 2 I acetone, water + KI O CH 2 CH 3 CH 3 (CH 2 ) 16 C Ethyl octadecanoate (95%) O OExample

+RX gives a thiol Hydrogen sulfide ion as the nucleophile.. S:S:S:S:.. H– + : X R.. S..H – Table 8.1 Examples of Nucleophilic Substitution

KSH + CH 3 CH(CH 2 ) 6 CH 3 Br ethanol, water + KBr + KBr 2-Nonanethiol (74%) CH 3 CH(CH 2 ) 6 CH 3 SH Example

+RX gives a nitrile Cyanide ion as the nucleophile – + : X R – C N:: C N: Table 8.1 Examples of Nucleophilic Substitution

DMSO Cyclopentyl cyanide (70%) Br NaCN+ CN + NaCN Example

+RX gives an alkyl azide Azide ion as the nucleophile + : X R –.. – N N N.. : : –+.. N N N.. :–+ Table 8.1 Examples of Nucleophilic Substitution

NaN 3 + CH 3 CH 2 CH 2 CH 2 CH 2 I 2-Propanol-water CH 3 CH 2 CH 2 CH 2 CH 2 N 3 + NaI Pentyl azide (52%) Example

+RX gives an alkyl iodide Iodide ion as the nucleophile + : X R – –.. : I.... : I..: Table 8.1 Examples of Nucleophilic Substitution

NaI is soluble in acetone; NaCl and NaBr are not soluble in acetone. acetone+NaI CH 3 CHCH 3 Br 63% +NaBr I Example

8.2 Relative Reactivity of Halide Leaving Groups

RI RBr RCl RF most reactive least reactive Generalization Reactivity of halide leaving groups in nucleophilic substitution is the same as for elimination.

BrCH 2 CH 2 CH 2 Cl + NaCN A single organic product was obtained when 1-bromo-3-chloropropane was allowed to react with one molar equivalent of sodium cyanide in aqueous ethanol. What was this product? Br is a better leaving group than Cl Problem 8.2

BrCH 2 CH 2 CH 2 Cl + NaCN A single organic product was obtained when 1-bromo-3-chloropropane was allowed to react with one molar equivalent of sodium cyanide in aqueous ethanol. What was this product? CH 2 CH 2 CH 2 Cl + NaBr C N: Problem 8.2

Feedback: Privacy Policy Feedback
Do Not Sell My Personal Information
About project: SlidePlayer Terms of Service

© 2025 SlidePlayer.com. Inc. All rights reserved.