Thiols. Thiols are less polar than alcohols MethanolMethanethiol bp: 65°C bp: 6°C.

Slides:



Advertisements
Similar presentations
Chapter 15 Alcohols, Diols, and Thiols
Advertisements

Ch 16 Amines Homework problems: 16.9, 16.10, 16.21, 16.25, 16.39,
Hydrocarbon Derivatives
Properties of Aldehydes and Ketones Chapter 13 Organic Compounds with oxygen and Sulfur.
Carboxylic Acids. A carboxylic acid contains a carboxyl group, which is a carbonyl group attach to a hydroxyl group. carbonyl group O  CH 3 — C—OH hydroxyl.
Aldehydes Ketones. Carbonyl group C = O Aldehydes Ketones Carboxylic acids Esters.
Alcohols & Phenols Dr. Shatha Alaqeel.
Alcohols, Ethers and Thiols Bettelheim, Brown, Campbell and Farrell Chapter 14.
Organic Chemistry II CHEM 271. Chapter One Alcohols, Diols and Thiols.
Sulfur-Containing Compounds
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic.
Chemistry 2100 Lecture 4. ALCOHOLSETHERSTHIOLS thiol / mercaptan (sulfhydryl) alcoholether.
Cysteine SMELLY STUFF Organic compounds having SH or Sulfhydryl functional group with strong and disagreeable odors. “ Also called mercaptans.
The functional group of a carboxylic acid is a carboxyl group
Chapter 7- Alcohols. Alcohols- commercially important Ethanol CH 3 CH 2 OH - Produced by fermentation or hydration of ethylene CH 2 =CH 2 + H 2 O H 2.
Alcohols can be thought of as organic relatives of water:
Alcohols, Ethers and Thiols
1 Chapter 13 Organic Compounds with Oxygen and Sulfur 13.3 Reactions of Alcohols and Thiols Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin.
Chapter 12 Organic Compounds with Oxygen and Sulfur
Properties of Alcohols, Ethers, and Thiols Chapter 12 Organic Compounds with Oxygen and Sulfur Copyright © 2005 by Pearson Education, Inc. Publishing.
Chemistry 121(01) Winter 2009 Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State)
Chemistry 2100 Chapter 14.
Chapter 8 Alcohols, Ehters and Thiols. Hydroxyl (OH) functional group Oxygen is sp 3 hybridized.
Chapter 13 Alcohols, Phenols, and Ethers Spencer L. Seager Michael R. Slabaugh Jennifer P. Harris.
Chapter 15 Amines Amines. Structure & Classification Amines are classified as 1°, 2°, or 3° depending on the number of carbon groups bonded to nitrogen.
Ch 12 Alcohols, Ether, Thiols Naming and Properties.
Chapter 8 Amines.
Chapter 16: Amines -N- - - Amines are classified as 1°, 2°, or 3° depending on the number of carbon groups bonded to nitrogen. Low molecular weight amines.
© 2003 Thomson Learning, Inc. All rights reserved General, Organic, and Biochemistry, 7e Bettelheim, Brown, and March.
Alcohols, Ethers, Thiols and Chirality
Chapter 14: Alcohols, Ethers, and Thiols Alcohol:OH(hydroxyl) group Alcohol: A compound that contains an -OH (hydroxyl) group bonded to a tetrahedral carbon.
Aspects 6/4/2016Dr Seemal Jelani Chem Structure of Alcohols The hydroxyl groups of alcohols are good hydrogen bonding donors and acceptors 6/4/2016Dr.
Chapter 14 Alcohols, Ethers, and Thiols Alcohols, Ethers, and Thiols.
Alcohols, Ethers, and Thiols
Chapter 5 Alcohols, Ethers, and Thiols. Alcohols Alcohol:OH(hydroxyl) group Alcohol: A compound that contains an -OH (hydroxyl) group bonded to a tetrahedral.
© 2003 Thomson Learning, Inc. All rights reserved General, Organic, and Biochemistry, 7e Bettelheim, Brown, and March.
© 2006 Thomson Learning, Inc. All rights reserved General, Organic, and Biochemistry, 8e Bettelheim, Brown Campbell, & Farrell.
Chapter 8 Amines Chemistry 20. Amines: Are derivatives of ammonia NH 3. Contain N attached to one or more alkyl (Aliphatic amine) or aromatic groups (Aromatic.
Organic Compounds that Contain Oxygen or Sulfur Three families of compounds that contain a C atom singly bonded to O or S are: 1.Alcohols, which contain.
Reactions of Oxacyclopropanes 9-9 Nucleophilic ring opening of oxacyclopropanes by S N 2 is regioselective and stereospecific. Oxacyclopropane can be ring-opened.
Chapter 12 Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds Organometallic Compounds Irene Lee Case Western Reserve University.
Alcohols, Ethers & Thiols
Alcohols, Ethers, Thiols and Chirality
13-1 Principles and Applications of Inorganic, Organic, and Biological Chemistry Denniston, Topping, and Caret 4 th ed Chapter 13 Copyright © The McGraw-Hill.
Chapter 11 Outline 11.1 Alcohols, Ethers, and Related Compounds
Chapter 13 Alcohols, Phenols, and Thiols
12 Chemistry 2.5 organic chemistry CR 07 Alcohols Alcohols have the function group –OH General formula: C n H 2n+1 OH or C n H 2n+2 O.
Chapter 15 Amines.
Chapter 13: Alcohols, Phenols, and Ethers
Alcohols Alcohols Contain a hydroxyl group (-OH).
Chapter 4: Carbon and the Diversity of Life Organic molecules: molecules that contain carbon Carbon: valence of 4 form 4 covalent bonds Variations in carbon.
Chapter 18 Carboxylic Acids Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Alcohols, Phenols, and Thiols Nanoplasmonic Research Group Organic Chemistry Chapter 7 Part I.
Chapter 13 Alcohols, Phenols, and Ethers Spencer L. Seager Michael R. Slabaugh Jennifer P. Harris.
Chapter 18: Carboxylic acids -C-OH = = O O -COOH OR Formic AcidAcetic AcidOxalic Acid.
1 Organic Chemistry Oxygen and Sulfur in Organic Compounds.
Chapter 15 Alcohols, Diols, and Thiols Sources of Alcohols.
Aldehyde and Ketones R- CH = O R – C – R y O Session 37.
Chapter 1.4 Alcohols, Ethers, and Thiols
Sulfur analogs of alcohols, phenols and ethers
General, Organic, and Biochemistry, 8e
Alcohols, Phenols &Thiols
Lecture 9 Monday 2/6/17.
Alcohols د. جهاد الماليطي.
Chapter 13: Alcohols, Phenols, and Ethers
Alcohols and Thiols Unit 11.
Alcohols, Ethers, and Thiols
1.4 cont’d ETHERS & THIOLS.
Alcohols & Phenols.
Thiols and Sulfides 340 Chem 1st 1439.
Presentation transcript:

Thiols

Thiols are less polar than alcohols MethanolMethanethiol bp: 65°C bp: 6°C

1. low molecular weight thiols have foul odors 2. hydrogen bonding is much weaker in thiols than in alcohols 3. thiols are stronger acids than alcohols 4. thiols are more easily oxidized than alcohols; oxidation takes place at sulfur Properties of Thiols

Nomenclature of Thiols 1) analogous to alcohols, but suffix is -thiol rather than -ol 2) final -e of alkane name is retained, not dropped as with alcohols CH 3 CHCH 2 CH 2 SH CH 3 3-Methyl-1-butanethiol

have pK a s of about 10; can be deprotonated in aqueous base stronger acid (pK a = 10) weaker acid (pK a = 15.7) Thiols are stronger acids than alcohols H RS OHOHOHOH –RS H OHOHOHOH – ++

RS – and HS – are weakly basic and good nucleophiles HClH C6H5SC6H5SC6H5SC6H5S C 6 H 5 SNa SN2SN2SN2SN2 (75%) KSH SN2SN2SN2SN2 (67%) BrSH

Oxidation of thiols take place at sulfur thiol (reduced) disulfide (oxidized) RS H RS SR thiol-disulfide redox pair is important in biochemistry other oxidative processes place 1, 2, or 3 oxygen atoms on sulfur

Oxidation of thiols take place at sulfur thioldisulfide sulfinic acid sulfonic acid RS H RS SR sulfenic acid RS OH RS OH O –+ RS OH O – 2+ O –

HSCH 2 CH 2 CH(CH 2 ) 4 COH SHSHSHSH O 2, FeCl 3 (CH 2 ) 4 COH  -Lipoic acid (78%) Example: sulfide-disulfide redox pair O OS S