by : Directorate of Education‚ Delhi SOME IMPORTANT REASONING BASED QUESTIONS OF ORGANIC CHEMISTRY 1. Chlorobenzene is less reactive than chloromethane. Ans. In chlorobenzene‚ each carbon atom of benzenering is sp2 hyridised and is electron withdrawing. Chlorine atom donates a lone pair of electron and acquire positive charge. The negative charge is delocalised on ortho and para position by resonance. C-Cl bond acquires partial double bond character and is 169 pm as compared to 17.0 pm in chloromethane
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CLASSIFICATION TESTS A. Acids There are relatively few suitable tests for carboxylic acids. Classification is based mostly upon solubility tests. If the compound is water soluble‚ test the aqueous solution of your compound with pH paper (also check the pH of the original water). If the compound is water-insoluble and it dissolves in 5% (1.5M) sodium hydroxide and 5% NaHCO3 solutions as performed in your solubility tests‚ it can be classified as a carboxylic acid. Establish an equivalence value
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Spectra Analysis Organic Chemistry Lab‚ CHEM 369 The University of Tennessee‚ Knoxville Dr. Smith Spectra 1: tert-butyl cyanoacetate Molecular formula: 141/13 = 10 R 11 => C10H10+11 => C10H21 C10H21NO2 – C3H10 = C7H11NO2 DBE: 2(#C - #H/2 - #X/2 + #N + 2)/2 =2(7 – 11/2 – 0/2 + 1 + 2)/2 = 3=> 1 double bond and 1 triple bond Mass spectrum table: m/z fragment |40
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J. of Advanced Engineering and Technology Vol. 2‚ No. 2 (2009) pp. 281-283 Synthesis of 2-Acetylcyclohexanone Using Pyrrolidine-enamine Eun-SunYoo Department of Oriental Medicine Industry‚ Honam University‚ Korea (Received : May. 20‚ 2009‚ Revised : Jun. 02‚ 2009‚ Accepted : Jun. 12‚ 2009) Abstract : 2-Acetylcyclohexanone was synthesized by acylation reaction of acidic anhydride using enamine as organiocatalyst instead of a strong base‚ NaOH‚ resulting in milder reaction conditions. The
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In the reaction mechanism‚ a carboxylic acid‚ m-toluic acid is used to synthesize N‚N-diethyl-m-toluamide‚ also know as DEET‚ through a nucleophilic acyl substitution reaction. The reaction begins by first converting the m-toluic carboxylic acid into an acyl chlorosulfite through a reaction using thionyl chloride. The carboxylic acid is converted into an acyl chloride because the acyl chloride is more reactive. In this step‚ hydrochloric acid is formed from a hydrogen on the carboxylic acid and a
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BACKROUND INFORMATION Organic chemistry is the study of hydrocarbons and their various deviations. (Ex. natural gas‚ paper‚ proteins‚ carbohydrates) Saturated hydrocarbons are hydrocarbons with carbon-carbon single bonds. (Ex. C-C) Unsaturated hydrocarbons are hydrocarbons with one of more multiple carbon-carbon bonds. (Ex. C=C double bond‚ triple bond‚ or both) Stereoisomers have the same molecular and structural formulas but different orientations of atoms in space. Constitutional isomers
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pair onto the amide oxygen (which makes the lone pair less available to the aromatic ring) and the increased steric bulk of the group‚ favouring substitution at the 4-position over the 2-positions which it shields. Aniline is the simplest aromatic amine and is synthesised by first nitrating benzene using a concentrated mixture of nitric acid and sulphuric acid to give nitrobenzene which is then hydrogenated in the presence of a nickel catalyst to give the final product. Aniline undergoes very readily
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method that effectively yield the same result as using the enolate approach without necessarily employing a strong base. This method is through enamine synthesis approach where the carbonyl compound to the acylated is first reacted with a secondary amine in an acid-catalysed reaction. Enols and enamines are similar in terms of chemical properties because they are all nucleophilic because of that lone pair of electrons. The mechanism of the enamine formation reaction has some illustration below;
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strength decreases as the distance of the halogen from carboxylic group increases. e) i.e.‚ Benzoic acid is stronger than acetic acid. Reason : due to –I effect of phenyl group. Relative basic strength of amines 1. All aliphatic amines are more basic than ammonia. e.g. Methyl amine is more basic than ammonia. Reason : Due to +I effect of methyl group. 2. Aniline is weaker base than Ammonia. Reason : Due to
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The reaction between alpha-amino acid and ninhydrin involved in the development of color are described by the following five mechanistic steps: alpha-amino acid + ninhydrin ---> reduced ninhydrin + alpha-amino acid + H2O alpha-amino acid + H2O ---> alpha-keto acid +NH3 alpha-keto acid + NH3 ---> aldehyde + CO2 Step (1) is an oxidative deamination reaction that removes two hydrogen from the alpha-amino acid to yield an alpha-imino acid. Simultaneously‚ the original ninhydrin is reduced
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