Organic Analytical Chemistry
, by Mohan, Jag
- ISBN: 9781842651193 | 1842651196
- Cover: Hardcover
- Copyright: 1/1/2003
Rapid developments in analytical techniques and the use of modern reagents in organic synthesis during the last two decades have revolutionized the approach to organic structure determination. As advanced topics in organic analysis such as spectroscopic methods are being introduced, this text will stimulate the interest of students.
| Preface | |
| Qualitative Analysis Organic Analysis of Functional Groups and Their Derivatization | p. 1 |
| Identification of Unknown Compounds | p. 3 |
| Preliminary examination | p. 3 |
| Ignition test | p. 4 |
| Solubility behaviour | p. 5 |
| Detection of extra-elements | p. 6 |
| The Lassaigne's Test | p. 7 |
| Middleton's method for the detection of extra elements in an organic compounds (sodium carbonate-zinc method) | p. 9 |
| Determination of functional groups: General procedure and mechanism of reactions | p. 10 |
| Functional groups having no extra elements (Compounds containing carbon, hydrogen with or without oxygen) | p. 10 |
| Functional groups having nitrogen as an extra element (compounds containing carbon, hydrogen, nitrogen with or without oxygen) | p. 32 |
| Functional groups having sulphur as an extra element (compounds containing carbon, hydrogen, sulphur with or without oxygen) | p. 43 |
| Functional groups having nitrogen and sulphur as extra elements (compounds containing carbon, hydrogen, nitrogen, sulphur with or without oxygen) | p. 45 |
| Functional groups having halogen as an extra element | p. 46 |
| Melting point, mixture melting point and boiling point | p. 49 |
| Preparation of derivatives of various functional groups (General procedure and mechanism) | p. 54 |
| Identification of Simple Binary and Ternary Mixtures of Organic Compounds | p. 85 |
| Types of Mixtures generally encountered | p. 85 |
| Determination of extra elements and functional groups | p. 85 |
| Separation of the mixture | p. 85 |
| Identification of individual components | p. 90 |
| Separation of Ternary Mixtures | p. 90 |
| Confirmatory Tests of Common Organic Compounds, Their Derivatization and Classified Tables Including Melting and Boiling Points | p. 93 |
| Compounds having no extra-elements | p. 93 |
| Nitrogen compounds | p. 140 |
| Halogen compounds | p. 172 |
| Sulphur compounds | p. 184 |
| Qualitative Analysis Spectral Methods | |
| Infrared Spectroscopy | p. 195 |
| Introduction | p. 195 |
| Basic theory | p. 195 |
| Double-beam infrared spectrometer | p. 196 |
| Fourier transform infrared spectrometer (FTIR) | p. 197 |
| Important useful terms concerning infrared spectroscopy | p. 204 |
| Infrared spectrum: functional group and fingerprint regions | p. 204 |
| Absorption of infrared radiation and molecular vibrations | p. 205 |
| Fundamental vibrations and overtones | p. 207 |
| Number of Fundamental vibrations and selection rules | p. 208 |
| Intensity and position of infrared absorption bands | p. 210 |
| Frequency shifts by change of phase and solvents | p. 210 |
| Interpretation of infrared spectra (general characteristics) | p. 211 |
| Characteristic absorptions frequencies of various functional groups in organic molecules | p. 212 |
| Interpretation of IR spectra of some representative compounds | p. 231 |
| Nuclear Magnetic Resonance Spectroscopy | p. 245 |
| Introduction | p. 245 |
| Behaviour of spin-active nuclei as spinning nuclear magnets | p. 245 |
| Orientation of spinning nuclear magnets in a uniform magnetic field and energy description in NMR phenomenon | p. 246 |
| Energy absorption (resonance) and relaxation | p. 246 |
| Energy absorption (resonance) | p. 246 |
| Relaxation | p. 247 |
| Continous wave (CW) NMR spectrometer and FT-NMR spectrometer | p. 247 |
| CW-NMR spectrometer | p. 247 |
| FT-NMR spectroscopy | p. 252 |
| Detector (detection of decay of magnetization-FID) | p. 254 |
| Rate of data sampling (dignitization) | p. 255 |
| Signal-to-noise ratio | p. 255 |
| Fourier transformation (conversion of time domain spectrum into the corrsponding Frequency domain spectrum) | p. 257 |
| Important useful terms involved in the interpretation of NMR spectrum | p. 257 |
| Chemical shift | p. 257 |
| Chemical shift parameters and internal standards | p. 258 |
| Shielding and deshielding of nucleaus caused by inductive and mesomeric effects | p. 260 |
| Anisotropic effect | p. 260 |
| Equivalence and non-equivalence of protons | p. 260 |
| Spin coupling or spin-spin splitting | p. 262 |
| Multiplicity of splitting and relative intensity of lines in a multiplet | p. 263 |
| Coupling constants | p. 264 |
| Integration | p. 265 |
| The approximate chemical shift values for various types of protons | p. 268 |
| Chemical shift values ([Delta]-units) for solvents and other simple substances in four NMR solvents | p. 268 |
| Shifts in the position of benzene protons ([Delta]=7.27) caused by various substituents (Table 2.7) | p. 270 |
| Interpretation of PMR spectra of some representative compounds | p. 271 |
| Mass Spectrometry | p. 281 |
| Introduction | p. 281 |
| Basic theory | p. 281 |
| Instrumentation-The mass spectrometer | p. 282 |
| Introduction of sample into mass spectrometer (inlet system) | p. 283 |
| Generation of positively charged ions in the ion source | p. 283 |
| Methods for separation of ions (mass analysers) | p. 288 |
| Detection of Ions | p. 295 |
| Important terms of mass spectrometry | p. 296 |
| Mass spectrum | p. 296 |
| Fragmentation: patterns and processes | p. 300 |
| Characteristic features and fragmentation patterns of various classes of compounds | p. 305 |
| Ultraviolet Spectroscopy | p. 347 |
| Basic Concepts and Instrumentation | p. 347 |
| Introduction | p. 347 |
| The ultraviolet spectrum | p. 347 |
| Electronic energy levels, electronic transitions and selection rules | p. 348 |
| Ultraviolet-visible spectrometer | p. 349 |
| Important useful terms concerning ultraviolet spectroscopy | p. 351 |
| Chromophores and auxochromes | p. 351 |
| Hyperchromic effect, hypochromic effect and Isosbestic point | p. 353 |
| Absorption of light by a solution (Absorption laws) and measurement of absorption intensity | p. 354 |
| Problems | p. 358 |
| Woodward and Fieser's rules for calculating ultraviolet absorption maxima | p. 359 |
| Woodward and Fieser's rules for calculating ultraviolet absorption maxima of of substituted diene (Ethanol solution) | p. 359 |
| Woodward-Fieser rules for calculating absorption maxima of carbonyl Compounds | p. 362 |
| Calculation of [gamma subscript max] values for substituted aromatic aldehydes, ketones car boxylic acids and esters | p. 365 |
| Chemical Analysis by Other Instrumental Techniques | p. 367 |
| Atomic emission spectroscopy | p. 367 |
| Electron spin resonance spectroscopy | p. 376 |
| Atomic absorption spectroscopy | p. 388 |
| Fluorimetry and phosphorimetry | p. 398 |
| Flame photometry | p. 409 |
| X-Ray methods | p. 414 |
| General Techniques Separation, Purification and Preparation of Organic Compounds | p. 425 |
| Separation and Purification of Organic Compounds | p. 427 |
| Separation and purification of organic solids | p. 427 |
| Separation and purification of organic liquids or low melting solids | p. 463 |
| Organic Preparations | p. 474 |
| One step preparations | p. 474 |
| Preparation of benzalacetophenone from acetophenone (Claisen-Schmidt reaction) | p. 474 |
| Preparation of cinnamic acid from malonic acid (Knoevenagel reaction) | p. 475 |
| Preparation of dimedone from mesityl oxide (Dieckmann condensation) | p. 475 |
| Preparation of 2,3-dimethyl anthraquinone from naphthaquinone and 2,3-dimethyl butadiene (Diels-Alder reaction) | p. 476 |
| Preparation of iodoform from acetone (Haloform reaction) | p. 477 |
| Preparation of isoborneol from camphor (sodium borohydride reduction) | p. 478 |
| Preparation of nylon 6-10 (Polyhexamethy lenesebacamide) from sebacoyl chloride and hexamethylenediamine (condensation polymerization) | p. 478 |
| Preparation of Polystyrene from styrene (Free radical addition Polymerization) | p. 479 |
| Preparation of phthalimide from phthalic anhydride (imide formation) | p. 480 |
| Preparation of triphenylcarbinol from benzophenone or ethyl benzoate (Grignard reaction) | p. 481 |
| Preparation of 1, 2, 3, 4-tetrahydrocarboazole from cyclohexanone (Fischer Indolisation reaction) | p. 482 |
| Preparation of camphorquinone from camphor by oxidation with selenium dioxide | p. 483 |
| Preparation of w-dimethylaminopropiophenone hydrochloride from dimethylaminehydrochloride (Mannich reaction) | p. 483 |
| Preparation of benzimidazole from o-phenylenediamine (cyclodehydration) | p. 484 |
| Preparation of 2-amino-4-methylthiazole from thiourea and chloroacetone | p. 485 |
| Preparation of benzotriazole from o-phenylenediamine | p. 485 |
| Two step preparations | p. 486 |
| Preparation of aspirin from phenol | p. 486 |
| Preparation of benzidine from azobenzene | p. 487 |
| Preparation of benzanilide from benzophenone | p. 488 |
| Preparation of p-bromo/nitro acetanilide from aniline | p. 490 |
| Preparation of 2-carbethoxycyclopentanone from adipic acid | p. 492 |
| Preparation of 2,4-dihydroxy acetophenone from hydroquinone | p. 493 |
| Preparation of 2,4-dinitrophenylhydrazine from chlorobenzene | p. 495 |
| Preparation of eosin from resorcinol | p. 496 |
| Preparation of methyl orange from aniline | p. 498 |
| Preparation of s-tribromobenzene from aniline | p. 499 |
| Preparation of 5-chloro-3-methylbenzothiophen from p-chlorothiophenol | p. 501 |
| Preparation of phenacetin from p-aminophenol | p. 502 |
| Preparation of benzofuran from salicyladehyde | p. 503 |
| Three Step preparations | p. 504 |
| Preparation of [proportional to]-acetylaminocinnamic acid from glycine | p. 504 |
| Preparation of acridone from anthranilic acid | p. 506 |
| Preparation of benzilic acidb from benzaldehyde | p. 509 |
| Preparation of m-nitroaniline from benzene | p. 511 |
| Preparation of 6 and 8-nitro-4-methyl-7-hydroxycoumarin from ethyl acetate | p. 513 |
| Preparation of 5-acetoxy-1,2-benzoxathiole-2-one from hydroquinone | p. 515 |
| Quantitative Elemental, Functional Groups and Biochemical Estimations | p. 517 |
| Quantitative Elemental Determination | p. 519 |
| Estimation of elements | p. 519 |
| Estimation of carbon and hydrogen | p. 519 |
| Estimation of nitrogen | p. 523 |
| Estimation of sulphur | p. 527 |
| Estimation of halogens | p. 528 |
| Estimation of Functional Groups | p. 531 |
| Estimation of hydroxyl and amino groups | p. 531 |
| Estimation of acetyl group, esters and amides | p. 532 |
| Estimation of carbonyl groups | p. 536 |
| Determination of molecular weight and percentage purity of carboxylic acid | p. 539 |
| Estimation of sugars | p. 541 |
| Estimation of unsaturation | p. 546 |
| Quantitative Biochemical Estimations | p. 549 |
| Estimation of carbohydrates by anthrone method | p. 549 |
| Estimation of amino acids using ninhydrin reaction | p. 549 |
| Quantative determination of ascorbic acid in plant tissues | p. 550 |
| Estimation of proteins in egg albumin | p. 551 |
| Biuret method | p. 551 |
| The Folin-Lowry method | p. 552 |
| Estimation of protein by ultraviolet absorption method | p. 552 |
| Estimation of free fatty acids (acid values) in oils/fats by direct titration method | p. 553 |
| Determination of iodine value (amount of unsaturation) of a fat or oil | p. 553 |
| Determination of saponification value of a fat or oil | p. 554 |
| Estimation of blood cholesterol by Liebermann-Burchard reaction | p. 555 |
| Estimation of DNA by reaction with diphenylamine | p. 556 |
| Estimation of RNA by using orcinol | p. 556 |
| Composite spectral problems | p. 559 |
| AIDS to Structural Information | p. 561 |
| Determination of molecular formula and the related structural information | p. 561 |
| Determination of molecular weight (high resolution mass spectrometry) | p. 561 |
| Determination of molecular formula by using rule of Thirteen | p. 561 |
| Determination of the index of hydrogen deficiency (unsaturation index) | p. 562 |
| Determination of number of double bond and/or ring equivalents (DBE) from the molecular formula of an organic compound | p. 564 |
| Application of Spectroscopic Techniques to structural Elucidation | p. 566 |
| Introduction | p. 566 |
| Structural information obtainable from different types of spectra | p. 566 |
| Procedure for elucidation of molecular structure by spectroscopic methods | p. 567 |
| Composite Problems with Solutions (Set I) | p. 569 |
| Interpretation of UV, IR, PMR and Mass Spectra for the Identification of Organic Compounds (Set II) | p. 579 |
| Unsolved Spectral Problems (Set III) | p. 599 |
| Appendices | p. 605 |
| General safety rules, safety equipment and first-aid | p. 607 |
| Chemo-toxins and related antidotes | p. 618 |
| Prevention and protection of explosion and fire hazards | p. 623 |
| Notes on special hazards | p. 630 |
| Safe disposal of reagents and derivatives | p. 636 |
| Purification of common organic solvents | p. 639 |
| Preparation of reagents | p. 644 |
| Further Reading | p. 647 |
| Index | p. 649 |
| Table of Contents provided by Ingram. All Rights Reserved. |
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