Stereochemistry Practice Problems With Answers
Cilinia Looker
Doing practice problems is the only way to master organic chemistry! At Chemistry Steps, you can find all the topics of Organic 1 and 2 and their associated practice problems. There are more than 1000 practice questions and you can find them after each article listed below.
Draw both chair conformation (ring-flip) and use the table to calculate the relative energy cost associated with each group in the axial position to determine the more stable chair conformation of each of the following compounds:
Determine the relationship in each of the following pairs. Do the drawings represent constitutional isomers or stereoisomers, or are they just different ways of drawing the same compound? If they are stereoisomers, are they enantiomers or diastereomers?
Explain your answer by converting the drawings into the same representation, i.e. if you are comparing a Newman projection to a Fischer projection, you need to convert both into either a Newman or Fischer projection. Assign all the absolute configurations as R or S if you hesitate.
On the following synthetic scheme, identify the reagents, in the correct order, that you would use to achieve the following synthetic transformations. Determine the structure of compounds A and B and the major organic products resulting from the alkyne.
Devise a synthesis of each of the following compounds using an arene diazonium salt. They all require more than one step and you may select the desired regioisomer (for example the para product from an ortho, para mixture) when needed.
his is a comprehensive practice problem on the alpha carbon chemistry. The topics covered range from the simple halogenation reactions of enols to multistep synthetic transformation.
All the practice problems are open to everyone for free! I have seen and prepared hundreds of exams for organic chemistry and these practice problems are the types that you will find in your exams. Their difficulty varies from one-step to more advanced ones including step organic synthesis problems.
Zoom links for all of the synchronous practice sessions (lecture), discussion sections, and office hours will be available throughout the quarter on the Zoom Information Page of the course Canvas site.
There are several formats available from the bookstore & other retails (hardcover, loose-leaf, eBook, rental, used, etc.) Any format is fine - pick whichever format will be most convenient and affordable for you.
The textbook authors have not included any of the answers to practice problems in the book itself. Instead, they have compiled complete solutions (and other useful summaries) in the Study Guide and Solutions Manual. It is sold as a separate volume. It is not a required companion to the textbook, but you may find it useful. If the libraries manage to reopen, they do have a copy available on reserve in Odegaard.
Particularly for Chapters 6 & 7, it is useful to have a molecular model kit. As long as you have the capability to generate tetrahedral carbon atoms, any model kit (or gummy bear & toothpick substitute) will do the trick.
Synchronous course lecture times (T-Th, 1:30-2:50pm) will be used to discuss the material, allow for Q&A with Dr. R, give an overview of upcoming assignments, and work through practice problems together. These Zoom sessions are not required and attendance will not be monitored. They will be recorded to allow for asynchronous viewing.
Sapling Learning. Practice is an important part of learning. This quarter, we will be using Macmillan's Sapling Learning platform for our homework practice problems. Assignments will be available for approximately 2 weeks prior to their deadlines. Due dates are noted in Canvas and in Sapling. To make sure your account is appropriately linked to the course gradebook, you should register through the link on the Canvas site (registration is $26/quarter when purchased directly through Sapling).
Scoring & Late Assignments. To receive full credit, you must submit the correct answer on the first attempt prior to the deadline shown in Sapling. If your initial submission is incorrect, you may resubmit answers for partial credit. Should unexpected circumstances arise that you are unable to complete your assignment by the due date, you will be able to submit responses in Sapling for an additional week for half of earned credit.
Every Wednesday, you will meet with your discussion section synchronously on Zoom. During this time, the teaching assistant will review some of the week's topics, provide time for questions, and guide the group through some practice problems. We encourage you to sign into the Zoom call with your video enabled when possible and on a device where you can access Google G-Suite functionalities to facilitate group work. There are 10 meetings of the discussion sections throughout the quarter, and participation credit will be given each week for your contributions to your breakout groups on worksheet questions. Two discussion sections participation scores will be dropped to allow for absences. No make-up assignments will be offered.
While most of the course content will be introduced in the synchronous lecture time, you may find it useful to review individual topics with the short content videos provided for each chapter. Most videos contain at least one concept check quiz that will pop up as you watch the video. Participation credit will be awarded if you have completed at least 90% of the concept check quizzes by the end of the quarter. (The correct answers do not need to be selected, but you must watch the video and select an answer).
We will have 4 midterm assessments and a cumulative final exam this quarter. The lowest midterm score will be dropped from your course grade to minimize the impact of illness, absence, or technical difficulty on your grade. The assessments will be posted as PDFs and available for download at 1:30pm on exam days. You will then be able to work through the exam (either filling in your answer on a printed copy, on a tablet/device, or on blank paper numbered according to the exam file). At the end of the exam time, you will create a PDF of your completed assessment and upload it to Gradescope. A practice upload and more specific instructions will be provided prior to the first exam.
Regrade policy. Exams are graded using specific rubrics within the Gradescope platform. If you would like a grader to revisit your exam, you may place that request through Gradescope within 1 week of the midterm scores being published to you.
Your experience in this class is important to us. It is the policy and practice of the University of Washington to create inclusive and accessible learning environments consistent with federal and state law. If you have already established accommodations with Disability Resources for Students (DRS), please communicate your approved accommodations to Dr. Robinson as soon as possible, so we can meet your needs and support your success in this course.
If you have not yet established services through DRS, but have a temporary health condition or permanent disability that requires accommodations, you are welcome to contact DRS at 206-543-8924 or uw...@uw.edu. DRS offers resources and coordinates reasonable accommodations for students with disabilities or temporary health conditions (mental health, attention-related, learning, vision, hearing, physical, or health impacts).
Washington state law requires that UW develop a policy for accommodation of student absences or significant hardship due to reasons of faith or conscience, or for organized religious activities. The UW's policy, including more information about how to request an accommodation, is available at Religious Accommodation Policy. Accommodations must be requested within the first two weeks of this course using the Religious Accommodations Request form.
It is very convenient for the student to review the general concepts acquired in the first year with the subject of Inorganic Chemistry and Equilibrium. In particular, the part that refers to chemical and acid-base balance. A minimum knowledge of organic formulation and nomenclature is required.
Remember that this is a subject where part of the assessment can be carried out during class (theory and / or problems). For this reason, it is highly recommended when enrolling, to consider possible overlaps with scheduled activities of other subjects.
Chemical bond. Lewis structures and resonance. Atomic orbitals, hybrid orbitals and molecular orbitals. Polarity. Intermolecular forces. Structures and formulas of organic molecules. Oxidation degree. Classification of compounds according to the degree of oxidation and their functional group. Thermodynamics and equilibrium. Kinetics and reaction mechanisms: elementary and multistep reactions, reaction coordinate and profile, transition state, reaction intermediates, catalysis. Organic nomenclature. Acids and Bases in Organic Chemistry. Nucleophile, Electrophile and Reaction Mechanisms.
Isomerism. Chirality. Stereogenic center. R/S nomenclature. Enantiomers and diastereomers. Racemic mixture. Fischer projections. Optical activity, optical purity. Isomerism of cis-trans alkenes (Z/E). Chiral molecules and their biological importance.
Classes of alkanes: homologous series. Physical properties. Sources for obtaining alkanes, oil fractional distillation. Alkane halogenation reactions: Homolytic and heterolytic bond breaking, chain reactions and reactivity / selectivity.
Physical properties. Sources of obtaining alkenes: cracking of naphtha. Obtaining alkenes by elimination. Hydrogenation reactions of alkenes. Alkene addition reactions. Isomerization of alkenes. Polymerization of alkenes. Alkene oxidation reactions. General reactivity of alkynes.
Alkyl halides, alcohols, ethers, amines, thiols, thioethers. Concepts: Nucleophile and electrophile. Nucleophilic substitution reactions (SN1-SN2 mechanisms). Elimination reactions (mechanisms E1-E2). Basicity and nucleophilicity.
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