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    Oragnic Chemistry 4th Ed[1]. - Study Guide and Solution Manual

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    Oragnic Chemistry 4th Ed (1) - Study Guide and Solution Manual

    Uploaded by

    Avinoam Markovich

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    Fs fe} to my students CHAPTER 1 SPECIAL TOPIC I CHAPTER 2 CHAPTER 3 SPECIAL TOPIC IL SPECIAL TOPIC III CHAPTER 4 SPECIAL TOPIC IV CHAPTER 5 TABLE OF CONTENTS Electronic Structure and Bonding + Acids and Bases Important Terms Solutions to Problems Practice Test pH, pKa, and Buffers Problems Solution to Problems ‘An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure Important Terms Solutions to Problems Practice Test 34 47 49 58 62 82 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity * ‘Thermodynamics and Kinetics Important Terms Solutions to Problems Practice Test Exercise in Drawing Curved Arrows Problems Answers Kinetics Problems Solutions to Problems Reactions of Alkenes Important Terms Solutions to Problems Practice Test Exercise in Model Building Stereochemistry: The Arrangement of Atoms in Space. The Stereochemistry of Addition Reactions Important Terms Solutions to Problems Practice Test 84 87 9 104 106 5 122 122 123 124 127 149) 151 152 158 192 TO THE STUDENT {As you study organic chemistry, make certain you fully understand each new fact that you encounter. While studying the material, you should be continuously asking yourself "why?": Why does that reaction occur? Why is that product formed? Why is that compound more stabie? If you truly understand each new piece of information, you will be creating a foundation upon which to lay subsequent information. A strong foundation will allow you to master a great deal of material with much less effort than you would have to put out if you were memorizing your way through the material Often it is the new vocabulary that you encounter when you are first exposed to a discipline that can be the biggest hurdle to mastering the material. For that reason I have included a list of the important terms and their definitions at the beginning of cach chapter in the Study Guide. Reading these is a good way to review some of the important aspects of the chapter. ‘There are two kinds of problems in the textbook. The problems at the end of each section within a chapter are designed to let you see if you have understood the material presented in that section, and to reinforce the material. You should do these problems as you encounter them. The problems at the end of each chapter integrate the concepts in the Chapter and sometimes include concepts that were mastered in previous chapters. Try to do as many of these as possible. The more problems you do, the more comfortable you will become with organic chemistry, and the more you Will enjoy it. Organic chemists use curved arrows to show the bonds that break and the bonds that form in an organic reaction. When you start studying organic reactions in Chapter 3, take time to do the exercise on drawing curved arrows that you will find on page 101. There is also an exercise in model building (page 151) that will help you with the material in Chapter 5. Good luck in your study. If you have any comments or suggestions about how the ‘Study Guide could be improved for those students who will follow you, I would be very happy to hear from you. Paula Yurkanis Bruice Department of Chemistry and Biochemistry University of California, Santa Barbara Santa Barbara, CA 93106 pybruice @chem.ucsb.edu CHAPTER 6 Reactions of Alkynes * Introduction to Multistep Synthesis Important Terms 194 Solutions to Problems 196 Practice Test 2u CHAPTER 7 Electron Delocalization, Resonance, and Aromaticity * More About Molecular Orbital Theory Important Terms 213 Solutions to Problems 215 Practice Test 234 CHAPTER 8 Reactions of Dienes * Ultraviolet/Visible Spectroscopy Important Terms 237 Solutions to Problems 240 Practice Test 262 CHAPTER 9 Reactions of Alkanes * Radicals Important Terms 265 Solutions to Problems 266 Practice Test 218 CHAPTER 10 Substitution Reactions of Alkyl Halides Important Terms 280 Solutions to Problems 282, Practice Test 300 CHAPTER 11 Elimination Reactions of Alkyl Halides + Competition Between Substitution and Elimination Important Terms 302 Solutions to Problems 303 Practice Test 330 CHAPTER 12 Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds * Organometallic Compounds Important Terms 332 Solutions to Problems 334 Practice Test 367 CHAPTER 13 Mass Spectrometry and Infrared Spectroscopy Important Terms 369 Solutions to Problems 371 Practice Test 392 CHAPTER 14 NMR Spectroscopy Important Terms 394 Solutions to Problems 397 Practice Test 420 CHAPTER 15 CHAPTER 16 CHAPTER 17 CHAPTER 18 CHAPTER 19 CHAPTER 20 CHAPTER 21 CHAPTER 22 CHAPTER 23 ‘Aromaticity + Reactions of Benzene Important Terms Solutions to Problems Practice Test Reactions of Substituted Benzenes Important Terms Solutions to Problems Practice Test Carbonyl Compounds I: Nucleophilic Acyl Substitution Important Terms Solutions to Problems Practice Test 422 424 437 439 441 477 479 482 514 Carbonyl Compounds Il: Nucleophilic Acyl Addition, Nucleophilic Acyl Substitution, and Nucleophilic Addition-Elimination + Reactions of o,B- Unsaturated Compounds Important Terms Solutions to Problems Practice Test Carbonyl Compounds III: Reactions at the a-Carbon Important Terms Solutions to Problems Practice Test More About Oxidation-Reduction Reactions Important Terms Solutions to Problems Practice Test More About Amines * Heterocyclic Compounds Important Terms Solutions to Problems Practice Test Carbohydrates Important Terms Solutions to Problems Practice Test Amino Acids, Peptides, and Proteins Important Terms Solutions to Problems Practice Test 516 519 552 554 556 596 598 600 626 628 630 657 659 662 678 680 683 703 CHAPTER 24 CHAPTER 25 CHAPTER 26 (CHAPTER 27 CHAPTER 28 CHAPTER 29 CHAPTER 30 Answers to Practice Tests Catalysis Important Terms Solutions to Problems ‘The Organic Mechanisms of the Coenzymes ‘Important Terms Solutions to Problems Lipids Important Terms Solutions to Problems Nucleosides, Nucleotides, and Nucleic Acids Imporant Terms Solutions to Problems Synthetic Polymers Important Terms Solutions to Problems Pericyclic Reactions Important Terms Solutions to Problems ‘The Organic Chemistry of Drugs: Discovery and Design ‘Important Terms Solutions to Problems 705 707 726 28 144 741 164 167 782 785 804 806 824 826 832 CHAPTER 1 Electronic Structure and Bonding Acids and Bases Important acid acid-base reaction acid dissociation constant acidity antibonding molecular orbital atomic number atomic orbital atomic weight aufbau principle base basicity bond dissociation energy bonding molecular orbital bond length Bronsted acid Bronsted base buffer solution carbanion carbocation condensed structure conjugate acid conjugate base a substance that donates a proton, a reaction in which an acid donates a proton to a base. a measure of the degree to which an acid dissociates. ‘a measure of how easily a compound gives up a proton. a molecular orbital that results when two atomic orbitals with opposite signs interact. Electrons in an antibonding orbital decrease bond strength. tells how many protons (or electrons) the neutral atom has. an orbital associated with an atom. the average mass of the atoms in the naturally occurring element. states that an electron will always go into the available orbital with the lowest energy. ‘a substance that accepts a proton. describes the tendency of a compound to share its electrons with a proton. the amount of energy required to break a bond homolytically (each of the atoms retains one of the bonding electrons) or the amount of energy released when a bond is formed. ‘a molecular orbital that results when two atomic orbitals with the same sign interact. Electrons in a bonding orbital increase bond strength. the internuclear distance between two atoms at minimum energy (maximum stability). a substance that donates a proton. a substance that accepts a proton. solution of a weak acid and its conjugate base. a compound containing a negatively charged carbon. a compound containing a positively charged carbon. a structure that does not show some (or all) of the covalent bonds. the compound formed when a base accepts a proton. the compound formed when an acid loses a proton. 2 Chapter 1 core electrons electrons in filled shells. covalent bond a bond created as a result of sharing electrons. degenerate orbitals orbitals that have the same energy. delocalized electrons electrons that do not belong to a single atom nor are they shared in a bond between two atoms. dipole a positive end and a negative end. dipole moment (4) a measure of the separation of charge in a bond or in a molecule. double bond composed of a sigma bond and a pi bond, electron affinity the energy given off when an atom acquires an electron. electronegative describes an element that readily acquires an electron electronegativity the tendency of an atom to pull electrons toward itself. electropositive describes an element that readily loses an electron. electrostatic attraction _an attractive force between opposite charges. electrostatic potential map a map that allows you to see how electrons are distributed in a molecule. equilibrium constant the ratio of products to reactants at equilibrium (or the ratio of the rate constants for the forward and reverse reactions). excited-state electronic the electronic configuration that results when an electron in the ground configuration state has been moved to a higher energy orbital. formal charge the number of valence electrons - (the number of nonbonding electrons + 1/2 the number of bonding electrons). free radical a species with an unpaired electron. (radical) ground-state electronic a description of which orbitals the electrons of an atom occupy when they configuration are all in their lowest energy orbitals. Heisenberg uncertainty states that both the precise location and the momentum of an atomic principle particle cannot be simultaneously determined. Henderson-Hasselbalch pK, = pH + log(HAJ/[A"] equation Hund's rule states that when there are degenerate orbitals, an electron will occupy an empty orbital before it will pair up with another electron, hybrid orbital an orbital formed by hybridizing (mixing) atomic orbitals. hydride ion a negatively charged hydrogen. hydrogen ion (proton) inductive electron withdrawal ionic bond ionic compound ionization energy isotopes Kekulé structure Lewis acid Lewis base Lewis structure lone-pair electrons mass number molecular orbital molecular orbital (MO) theory node nonbonding electrons nonpolar covalent bond octet rule orbital orbital hybridization organic compound Pauli exclusion principle pH pi (m) bond Chapter! 3 a positively charged hydrogen. the pull of electrons through sigma bonds by an atom or a group of atoms. abond formed through the attraction of two ions of opposite charges. a compound composed of a positive ion and negative ion. the energy required to remove an electron from an atom. atoms with the same number of protons but a different number of neutrons. a model that represents the bonds between atoms as lines. a substance that accepts an electron pair. a substance that donates an electron pair. a model that represents the bonds between atoms as lines or dots and the rnonbonding electrons as dots. valence electrons not used in bonding. the number of protons plus the number of neutrons in an atom, an orbital associated with a molecule. describes a model in which the electrons occupy orbitals as they do in atoms but the orbitals extend over the entire molecule. a region within an orbital where there is zero probability of finding an electron. valence electrons not used in bonding. a bond formed between two atoms that share the bonding electrons equally. states that an atom will give up, accept, or share electrons in order to achieve a filled shell. Because a filled second shell contains eight electrons, this is known as the octet rule. the volume of space around the nucleus where an electron is most likely to be found. mixing of atomic orbitals. ‘a.compound that contains carbon. states that no more than two electrons can occupy an orbital and that the ‘two electrons must have opposite spin. the pH scale is used to describe the acidity of a solution (pH = -log{H*)). a bond formed as a result of side-to-side overlap of p orbitals. 4 Chapter 1 PKa polar covalent bond potential map describes the tendency of a compound to lose a proton (pKa = -log Ka, where Ka is the acid dissociation constant). bond formed between two atoms that do not share the bonding electrons equally. a map that allows you to see how electrons are distributed in a molecule, (electrostatic potential map) proton proton transfer reaction quantum mechanics radical (free radical) resonance resonance contributors resonance hybrid sigma (6) bond single bond tetrahedral bond angle tetrahedral carbon trigonal planar carbon triple bond valence electrons valence shell electron pair repulsion (VSEPR) model wave equation wave functions 4 positively charged hydrogen; a positively charged atomic particle. reaction in which a proton is transferred from an acid to a base, the use of mathematical equations to describe the behavior of electrons in atoms or molecules, a species with an unpaired electron. having delocalized electrons. structures with localized electrons that approximate the true structure of a compound with delocalized electrons. the actual structure of a compound with delocalized electrons. a bond with a symmetrical distribution of electrons about the internuclear axis. a single pair of electrons shared between two atoms. the bond angle (109.5°) formed by an sp’ hybridized central atom an sp? hybridized carbon; a carbon that forms covalent bonds using four sp? hybrid orbitals. an sp? hybridized carbon, composed of a sigma bond and two pi bonds. an electron in an outermost shell. a model that combines the concepts of atomic orbitals and shared electron pairs with minimization of electron repulsions an equation that describes the behavior of each electron in an atom or a molecule. a series of solutions of a wave equation. Chapter] 5 Solutions to Problems 1, The mass number = the number of protons + the number of neutrons The atomic number = the number of protons. All isotopes have the same atomic number; in the case of oxygen itis 8. ‘Therefore: ‘The isomer of oxygen with a mass number of 16 has 8 protons and 8 neutrons. The isomer of oxygen with a mass number of 17 has 8 protons and 9 neutrons. The isomer of oxygen with a mass number of 18 has 8 protons and 10 neutrons. 2. Using the aufbau principle (electrons go into available orbitals with the lowest energy) and the Pauli exclusion principle (no more than 2 electrons in each atomic orbital), and remembering that the relative energies of the atomic orbitals are: Is<2s<2p <3s<3p<4s<3d<4p<5s<4d

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