VJC 2025 J2 H2 Chemistry Hydroxy Compounds Notes& Tutorial Student

VICTORIA JUNIOR COLLEGE CHEMISTRY DEPARTMENT Mr Tan Yong Khai/tan.yong.khai@vjc.edu.sg JC2 H2 CHEMISTRY HYDROXY COMPOUNDS (ALCOHOLS & PHENOLS) Lecture 1 2 Pages 1 – 9 10 – 14 Complete by T1W5 T1W5 Tutorial questions 1 – 3 4 – 7 ______________________________________________________________________________ LECTURE OUTLINE 1 Alcohols 1.1 Introduction (Nomenclature/Structure) 1.2 Physical Properties 1.2.1 Boiling point 1.2.2 Solubility 1.2.3 Acidity 1.3 Laboratory Preparation 1.3.1 From Alkenes 1.3.2 From Nucleophilic Substitution of Halogenoalkanes 1.3.3 From Reduction of Carboxylic Acids 1.3.4 From Reduction of Aldehydes and Ketones 1.4 Reactions 1.4.1 Complete Combustion 1.4.2 Nucleophilic Substitution to Halogenoalkanes 1.4.3 Redox (Acid-Metal) Reaction with Sodium 1.4.4 Oxidation to Carbonyl Compounds and Carboxylic Acids 1.4.5 Dehydration to Alkenes 1.4.6 Condensation to Esters 1.4.7 Tri-Iodomethane (Iodoform) Formation 2 Phenols 2.1 Introduction 2.2 Physical Properties 2.2.1 Appearance 2.2.2 Boiling point 2.2.3 Solubility 2.2.4 Acidity 2.3 Reactions 2.3.1 Reaction of the Hydroxy Group 2.3.2 Electrophilic Substitution at Benzene Ring 2.3.3 Reaction with Neutral FeCl3(aq) 3 Summary

2 REFERENCES 1 Modern Organic Chemistry by R.O.C. Norman and D.J.Waddington 2 Principles of Organic Chemistry by Peter R.S. Murray 3 A-Level Chemistry by E.N. Ramsden 4 Chemistry in Context by Hill and Holman LEARNING OUTCOMES Candidates should be able to: (a) recall the chemistry of alcohols, exemplified by ethanol: (i) combustion (ii) nucleophilic substitution to give halogenoalkanes (iii) reaction with sodium (iv) oxidation to carbonyl compounds and carboxylic acids (v) dehydration to alkenes (b) suggest characteristic distinguishing reactions for the different classes of alcohols ( primary, secondary and tertiary alcohols), e.g. mild oxidation (c) deduce the presence of a CH3CH(OH)– group in an alcohol from its reaction with alkaline aqueous iodine to form tri-iodomethane (d) recall the chemistry of phenol, as exemplified by the following reactions: (i) with bases (ii) with sodium (iii) nitration of, and bromination of, the benzene ring (e) explain the relative acidities of water, phenol and ethanol in aqueous medium (interpret as Brønsted-Lowry acids)

Alcohols Victoria Junior College 1 1 Alcohols 1.1 Introduction (Nomenclature/Structure) Nomenclature  General formula of CnH2n+1OH or CnH2n+2O.  Ending ‘−e’ of corresponding alkane is replaced by the suffix ‘−ol’.  Position of –OH group in carbon chain is specified by inserting the appropriate number between the stem of the name and the ‘−ol’.  When choosing the parent of an alcohol, identify the longest chain that includes the carbon atom connected to the –OH group.  When numbering the parent chain of an alcohol, the C atom to which the –OH gr