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Organic Chemistry:Principles and Mechanisms Second Edition Joel M. Karty
James Wollack
ST. CATHERINE UNIVERSITY
Christopher Markworth
WESTERN WASHINGTON UNIVERSITY
Jennifer Griffith
WESTERN WASHINGTON UNIVERSITY
n W • W • NORTON & COM PANY • NEW YORK • LONDON
W. W. Norton & Com pany has been in dep en dent since its founding in 1923, when William Warder Norton and
Mary D. Herter Norton first published lectures delivered at the P eople’s Institute, the adult education division of New
York City’s Cooper Union. The firm soon expanded its program beyond the Institute, publishing books by celebrated
academics from Amer i ca and abroad. By midcentury, the two major pillars of Norton’s publishing program— trade
books and college texts— were firmly established. In the 1950s, the Norton f amily transferred control of the com
pany to its employees, and today— with a staff of four hundred and a comparable number of trade, college, and
professional titles published each year— W. W. Norton & Com pany stands as the largest and oldest publishing house
owned wholly by its employees.
,DOWNLOAD THE Test Bank for Organic Chemistry Principles and Mechanisms
2nd Edition Karty
Copyright © 2018, 2014 by W. W. Norton & Com pany, Inc.
All rights reserved.
Associate Media Editor: Arielle Holstein
Associate Managing Editor, College: Carla L. Talmadge
Production Man ag er: Eric Pier- Hocking
Assistant Media Editor: Doris Chiu
Composition by Westchester Publishing Ser vices
W. W. Norton & Com pany, Inc., 500 Fifth Ave nue, New York, NY 10110
wwnorton . com
W . W. Norton & Com pany Ltd., 15 Carlisle Street, London W1D 3BS
1 2 3 4 5 6 7 8 9 0
CONTENTS
Preface v
Chapter 1 | Atomic and Molecular Structure 1
Interchapter A | Nomenclature: The Basic System for Naming S imple Organic
Compounds— Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes,
and Ethers 35
Chapter 2 | Three- Dimensional Geometry, Intermolecular Interactions, and
Physical Properties 47
Chapter 3 | Orbital Interactions 1: Hybridization and Two- Center Molecular Orbitals 75
Interchapter B | Naming Alkenes, Alkynes, and Benzene Derivatives 103
Chapter 4 | Isomerism 1: Conformers and Constitutional Isomers 114
Chapter 5 | Isomerism 2: Chirality, Enantiomers, and Diastereomers 143
Interchapter C | Stereochemistry in Nomenclature: R and S Configurations about
Asymmetric Carbons and Z and E Configurations about Double Bonds 172
Chapter 6 | The Proton Transfer Reaction: An Introduction to Mechanisms,
Thermodynamics, and Charge Stability 184
Chapter 7 | An Overview of the Most Common Elementary Steps 211
Interchapter D | Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions 243
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, Interchapter E | Naming Compounds with a Functional Group That Calls for a
Suffix 1: Alcohols, Amines, Ketones, and Aldehydes 254
Chapter 8 | An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and
Their Comparisons to SN2 and E2 Reactions 265
Chapter 9 | Nucleophilic Substitution and Elimination Reactions 1: Competition
among SN2, SN1, E2, and E1 Reactions 292
Interchapter F | Naming Compounds with a Functional Group That Calls for a
Suffix 2: Carboxylic Acids and Their Derivatives 320
Chapter 10 | Nucleophilic Substitution and Elimination Reactions 2: Reactions
That Are Useful for Synthesis 331
Chapter 11 | Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Brønsted
Acid 361
Chapter 12 | Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving
Cyclic Transition States 388
Chapter 13 | Organic Synthesis 1: Beginning Concepts in Designing Multistep Synthesis 415
Chapter 14 | Orbital Interactions 2: Extended π Systems, Conjugation, and Aromaticity 445
Chapter 15 | Structure Determination 1: Ultraviolet– Vis i ble and Infrared Spectroscopies 469
Chapter 16 | Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy
and Mass Spectrometry 500
Chapter 17 | Nucleophilic Addition to Polar π Bonds 1: Addition of Strong Nucleophiles 533
Chapter 18 | Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and Acid
and Base Catalysis 567
Chapter 19 | Organic Synthesis 2: Intermediate Topics in Synthesis Design, and
Useful Redox and Carbon– Carbon Bond- Forming Reactions 606
Chapter 20 | Nucleophilic Addition– Elimination Reactions 1: The General
Mechanism Involving Strong Nucleophiles 645
Chapter 21 | Nucleophilic Addition– Elimination Reactions 2: Weak Nucleophiles 681
Chapter 22 | Aromatic Substitution 1: Electrophilic Aromatic Substitution on
Benzene; Useful Accompanying Reactions 723
Chapter 23 | Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings 752
Chapter 24 | The Diels– Alder Reaction and Other Pericyclic Reactions 790
Chapter 25 | Reactions Involving Free Radicals 826
Interchapter G | Fragmentation Pathways in Mass Spectrometry 856
Chapter 26 | Polymers 876
Credits 902
, DOWNLOAD THE Test Bank for Organic Chemistry Principles and Mechanisms
2nd Edition Karty
PREFACE terms of what they know, what they don’t know, and
the depth of their knowledge. Accurate assessments of
student mastery allow instructors to focus on areas
where students need the most help in learning.
HOW DOES IT WORK?
For each chapter, the learning objectives that students
could be expected to master by reading the text are
listed. The questions are identified as remembering,
understanding, applying, analyzing, evaluating, and
creating. This classification is patterned after Bloom’s
taxonomy of educational objectives. Bloom listed six
When was the last time you w ere pleased with the levels of learning: knowledge (information),
consistency and quality of the assessment comprehension, application, analy sis, synthesis, and
supplements that come with introductory texts? If you evaluation. Questions are also posed at three difficulty
are like most professors, you prob ably find that t hese levels: easy, medium, and difficult. By asking students
assessment packages do not always meet your needs. questions that vary in both type and level of difficulty,
To address this issue, Norton has collaborated with instructors can gather dif fer ent types of evidence,
Valerie Shute (Florida State University) and Diego which w ill allow them to more effectively assess how
Zapata- Rivera (Educational Testing Ser vices) to well students understand specific concepts.
develop a methodology for delivering high- quality,
valid, and reliable assessment supplements through Six Question Types (classified according to Bloom’s
our Test Banks and extensive suite of support taxonomy):
materials.
1. Remembering questions— Test declarative
knowledge, including textbook definitions and
WHY A NEW APPROACH? relationships between two or more pieces of
information. Can students recall or remember the
In evaluating the test banks that accompany information in the same form it was learned?
introductory texts, we found four substantive prob 2. Understanding questions— Pose prob lems in a
lem areas associated with the questions: context dif fer ent from the one in which the
material was learned, requiring students to draw
1. Test questions were misclassified in terms of type
from their declarative and/or procedural
and difficulty.
understanding of impor tant concepts. Can students
2. The prevalence of low- level and factual questions
explain ideas or concepts?
misrepresented the goals of the course.
3. Applying questions— Ask students to draw from
3. Topics w ere unevenly distributed: Trivial topics
their prior experience and use critical- thinking
were tested via multiple items, while impor tant
skills to engage in qualitative reasoning about the
concepts were not tested at all.
real world. Can students use learned information in
4. Links to course topics w ere too general, thus
another task or situation?
preventing diagnostic use of the item information.
4. Analyzing questions— Test students’ ability to break
down information and see how dif fer ent ele ments
STUDENT COMPETENCIES AND EVIDENCE- relate to each other and to the whole. Can students
CENTERED DESIGN distinguish among the dif fer ent parts?
5. Evaluating questions— Ask students to assess
We first conducted a focus group with the brightest information as a whole and frame their own
minds in educational testing to create a new model for argument. Can students justify a stand or decision?
assessment. A good assessment tool needs to do 6. Creating questions— Pose questions or objectives
several things: (a) define what students need to know that prompt students to put ele ments they have
and the level of knowledge and skills expected; (b) learned together into a coherent w hole to generate
include test items that assess the material to be new ideas. Can students create a new product or
learned at the appropriate level; and (c) enable point of view based on data?
instructors to accurately judge students’ mastery of
the material based on the assessment outcomes in Three Difficulty Levels:
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