Browse Course Material

Course info, instructors.

  • Dr. Kimberly Berkowski
  • Prof. Timothy F. Jamison

Departments

As taught in.

  • Organic Chemistry

Learning Resource Types

Organic chemistry ii.

facebook

You are leaving MIT OpenCourseWare

Chemistry Steps

Chemistry Steps

organic synthesis problems and solutions pdf

Organic Chemistry

Organic synthesis problems.

Organic Chemistry Practice Problems can be found after each topic covered in Chemistry Steps. The list of topics can be found here , and below are some examples of what you will find.

Organic Chemistry 1 Synthesis Problems

Nucleophilic substitution and elimination reactions, practice problems.

Predict the mechanism as SN1, SN2, E1 or E2 and draw the major organic product formed in each reaction. Consider any regioselectivity and stereoselectivity where applicable:

organic synthesis problems and solutions pdf

Answers and Solutions

Reactions of Alkenes Practice Problems

This is a comprehensive problem that covers the following topics and will serve as a review of all of them:

Substitution and elimination reactions.  Particularly,  substitution and elimination reactions of alcohols , the  regio – and stereochemistry of E2 reactions, and E2 reaction of cyclohexanes .

Mesylation and tosylation in Substitution and elimination reactions. 

Hydrohalogenation of alkenes according to Markovnikov’s rule .

Radical hydrohalogenation of alkenes .

Hydroboration-Oxidation of Alkenes .

Halogenation of alkenes through halohydrin formation .

Syn and anti dihydroxylation of alkenes.

Elimination reactions: Zaitsev and Hoffman products .

Ozonolysis of Alkenes.

organic synthesis problems and solutions pdf

Attempt to solve the entire problem before accessing the answers!

The  answers  will give you the structure of the  final product(s) only . Use this as a hint to determine the compounds formed after the first and second reactions.

Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:

organic synthesis problems and solutions pdf

Reactions of Alkynes Practice Problems

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.

organic synthesis problems and solutions pdf

Organic Chemistry 2 Practice Problems

Alcohols practice problems.

Predict the major organic product(s) for the following Grignard reactions of a ketone, aldehyde, ester, carbon dioxide and an epoxide:

organic synthesis problems and solutions pdf

The Diels-Alder Reaction Practice Problems

For each Diels–Alder reaction, predict the major product(s) with correct stereochemistry when each cyclic  diene is reacted with a dienophile:

organic synthesis problems and solutions pdf

Aromatic Substitution Practice Problems

Show how each compound can be synthesized from benzene and any other organic or inorganic reagents.

The order of reactions is very important!  So, before every step,  consider the ortho – ,  para – ,  or meta directing effect  of the current group on the aromatic ring.

organic synthesis problems and solutions pdf

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.

organic synthesis problems and solutions pdf

Aldehydes and Ketones Practice Problems

Predict the major product(s) obtained when each of the following compounds undergoes hydrolysis in the presence of an acid:

organic synthesis problems and solutions pdf

 Carboxylic Acids and Their Derivatives Practice Problems

Predict the  major organic product(s)  for each of the following reactions. They  all involve carboxylic acid derivatives  such as  esters, acid chlorides, nitriles, anhydrides, and amides . You may also need to go over the reactions covered in earlier chapters, particularly, the  Grignard  and  Gilman  reagents,  oxidizing  and  reducing   agents  and  electrophilic aromatic substitutions .

A link to each topic encountered in a given problem will be provided in the answer tab.

organic synthesis problems and solutions pdf

Alpha Carbon Chemistry – Enols and Enolates Practice Problems

This 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 .

To correctly answer these questions, you need to review the main principles of enolate chemistry – direct enolate alkylation, aldol condensation, crossed aldol condensation, alkylation using acetoacetic ester synthesis, malonic ester synthesis, the Stork enamine synthesis, Claisen condensation, Michael addition, and Robinson annulation.

organic synthesis problems and solutions pdf

CS Prime membership will also grant you access to multiple-choice quizzes !

If you are towards the end of your Organic 2 semester having covered most of the topics and ready for some more challenging synthesis problems – you are in the right place! In these practice problems, we will go over multistep organic synthesis.

Check also our new synthesis puzzles!

organic synthesis problems and solutions pdf

Go ahead and give it a try!

organic synthesis problems and solutions pdf

Determine the structure of each unknown in the following synthesis problems:

Keep in mind that it is rare to perform synthesis where only one product is formed and most often there is a need for isolating and purifying the desired product. So in this set of problems, you can choose a route where the target product is obtained as a mixture, even though it is desirable to design a synthesis where the yield of the target compound is in a reasonable range.

organic synthesis problems and solutions pdf

This content is for registered users only.

Click here to Register!

By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems including over 20 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, and t he powerful set of Organic Chemistry 1 and 2 Summary Study Guides .

organic synthesis problems and solutions pdf

Check Also:

  • Carboxylic Acids and Their Derivatives Practice Problems
  • Acetals as Protecting Groups for Aldehydes and Ketones
  • How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
  • Alkene Reactions Practice Problems
  • Changing the Position of a Double Bond
  • Changing the Position of a Leaving Group
  • Alkenes Multi-Step Synthesis Practice Problems
  • Alkyne Synthesis Reactions Practice Problems
  • Radical Halogenation in Organic Synthesis
  • Grignard Reaction in Organic Synthesis with Practice Problems
  • Ortho Para Meta Directors in Electrophilic Aromatic Substitution with Practice Problems
  • Orientation in Benzene Rings With More Than One Substituent

IMAGES

  1. Grignard Reaction in Organic Synthesis with Practice Problems

    organic synthesis problems and solutions pdf

  2. synthesis problems and answers

    organic synthesis problems and solutions pdf

  3. Economico Vegetazione principalmente organic chemistry cheat sheet Patrocinare spalla Affidabile

    organic synthesis problems and solutions pdf

  4. Organic Synthesis Solutions Manual

    organic synthesis problems and solutions pdf

  5. Solved These are multi step synthesis problems for Organic

    organic synthesis problems and solutions pdf

  6. Organic synthesis

    organic synthesis problems and solutions pdf

VIDEO

  1. Example:-12.1to10

  2. Synthesis Problems

  3. Synthesis Problems 2

  4. Lecture Designing Organic Syntheses 8 Prof G Dyker 311014

  5. Lecture Designing Organic Syntheses 7 Prof G Dyker 291014

  6. A2 organic synthesis problems from www.ChemistryTuition.Net

COMMENTS

  1. PDF ORGANIC CHEMISTRY I

    organic chemistry i - practice exercise alkene reactions and mechanisms for questions 1-24, give the major organic product of the reaction, paying particular attention to regio- and stereochemical outcomes. 1) o hcl ch3oh 2) hcl ch3 3) hcl 4) hcl 5) hbr 6) hcl 7) ch3 h3o + 8) h3o + 9) h3o + 10) hg(oac)2, h2o nabh4 ch3 11) hg(oac)2, h2o nabh4

  2. PDF Practice Sets, Organic Chemistry I Table of Contents

    Test 3 PS4: Test 3 Extra Synthesis Practice (6 pages) 45 Test 4 PS1: Test 4 HBr Addn to Dienes; NBS Allylic Bromination 51 Test 4 PS2: Test 4 Conjugation-Allylic-Diels-Alder Practice 55 Test 4 PS3: Aromatic Substitution Mechanisms (Products Provided) 57

  3. Exams

    Organic Chemistry II. Menu. More Info Syllabus Calendar Readings Lecture Notes Assignments Exams Exams. 2006 Exams. EXAMS SOLUTIONS Exam 1 Exam 2 Exam 3 ... assignment_turned_in Problem Sets with Solutions. grading Exams with Solutions. notes Lecture Notes. Download Course.

  4. PDF PRACTICE EXERCISE

    20) Provide the structure of the major organic product(s) in the reaction sequence below. CCH Sia2BH H2O2 OH-21) Provide the structure of the major organic product(s) in the reaction below. 1) O3 2) H2O 22) To a solution of propyne in diethyl ether, one molar equivalent of CH3Li was added and the resulting mixture was stirred for 0.5 hour.

  5. PDF Practice Sets

    Test 1 PS#4: Alcohol-Related Retrosynthesis Problems 15 Test 2 PS#1: Jasperse NMR Problems (this will only show the first ten or 42. It will have link to the full 42-problem practice set, which are also included in the class notes. 17 Test 3 PS1: Mechanism Practice (Many) 27 Test 3 PS2: Retrosynthesis + Synthesis Design Practice 35

  6. PDF Some Organic Synthesis Practice Problems: Starting from 1-hexene, 1

    Some Organic Synthesis Practice Problems: Starting from 1-hexene, 1-butyne, bromoethane, iodomethane and any reagent needed (you do not need to use all of these compounds), synthesize: 1. ClCl CHCl3, KOH Li, NH3 H3CCCCH2CH3 HCCCH2CH3 NaNH2, NH3, CH3I 2. H O 1) BH3 2) NaOH, H2O2 H2O H3CH2CH2CH2CCCH Br Br NaNH2 Br2 3. octane H3CH2CH2CH2CCCCH2CH3 ...

  7. PDF Undergraduate Organic Synthesis Guide

    Chem 30 - Synthesis Review Guide to Solving Sophomore Organic Synthesis Problems Disclaimer Omission of a topic on this handout does not preclude that material from appearing on the final exam. Any material that we have covered in lectur e, in a problem set, or in the book is fair game. The exam is cumulative and may include

  8. PDF Solutions For Modern Organic Synthesis An Introduction

    Solutions Manual for Modern Organic Synthesis: An Introduction Michael Nantz,Hasan Palandoken,George S. Zweifel,2006-08-18 This supplement includes the end-of-chapter problems from the main text, detailed solution sets, and an extra section of similar problems for grad students to study. Modern Organic Synthesis + Solutions Manual George ...

  9. PDF ORGANIC SYNTHESIS PROBLEMS

    1) 2) 3) 4) 5) 6) bromoethane —¥ ethyl ethanoate cold, aq NaOH nucleophilic substitution propene 2-methylpropylamine chloroethane ethanoic acid

  10. PDF assets.openstax.org

    assets.openstax.org

  11. PDF Test 3 Extra Synthesis Practice

    For each problem there will be multiple satisfactory solutions. 48. Provide a possible structure for compound with formula C5H8, given that it reacts with excess H2/Pt to give C5H10. 49. Provide a possible structure for a compound with formula C6H8, given that it reacts with excess H2/Pt to give C6H12.

  12. PDF Workbook for Organic Synthesis

    Workbook for organic synthesis : the disconnection approach / Stuart Warren and Paul Wyatt. - 2nd ed. p. cm. Includes bibliographical references and index. ISBN 978--470-71227-6 - ISBN 978--470-71226-9 1. Organic compounds - Synthesis - Textbooks. I. Wyatt, Paul. II. Title. QD262.W93 2009 547 .2 - dc22 2009030810

  13. Organic Chemistry Practice Problems-Chemistry Steps

    By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems including over 20 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides. 3. This content is for registered users only.

  14. PDF MODERN METHODS OF ORGANIC SYNTHESIS

    Formation of carbon-carbon single bonds. 1.1 Main-group chemistry. 1.1.1 Alkylation of enolates and enamines. 1.1.2 Conjugate addition reactions of enolates and enamines. 1.1.3 The aldol reaction. 1.1.4 Asymmetric methodology with enolates and enamines. 1.1.5 Organolithium reagents. 1.1.6 Organomagnesium reagents.

  15. PDF Organic Chemistry Practice Problems

    Organic Chemistry Practice Problems Organic Chemistry I Practice Set #11 (Chapters 8-10 - Carey) 1) For the following compound, provide a name. Be sure to identify stereoisomers properly. 2) Fill in what is missing. Either give all of the missing reagents to complete the reaction or give a structural formula for the major organic product(s). Show

  16. Organic Chemistry Practice Problems at Michigan State University

    Most organic chemistry textbooks contain a broad assortment of suitable problems, and paperback collections of practice problems are also available. The following web-sites provide nice collections of problems and answers: MIT Open CourseWare Reaction quizzes and summaries from Towson University Electronic flashcards from Ohio State University

  17. Worked Solutions in Organic Chemistry

    This book illustrates and teaches the finer details of the tactics and strategies employed in the synthesis of organic molecules. As well as providing model answers to the problems, the book discusses, in detail, the reasons why particular strategies are chosen, and why, in given circumstances, alternative methods or routes may or may not be appropriate.

  18. Problems in Organic Synthesis

    Problems in Organic Synthesis provides over 100 new and challenging problems, designed to aid in the mastery of organic synthesis. While written to be a companion text to Modern Organic Synthesis, it can serve as a supplement to any organic synthesis course. Problems in Organic Synthesis features chemistry from the current literature and addresses recent advances in the field.

  19. PDF Minnesota State University Moorhead

    Minnesota State University Moorhead

  20. Solutions Manual for Modern Organic Synthesis: An Introduction

    This supplement includes the end-of-chapter problems from the main text, detailed solution sets, and an extra section of similar problems for grad students to study. Sign in. Hidden fields. ... Solutions Manual for Modern Organic Synthesis: An Introduction, Volume 2. Michael Nantz, Hasan Palandoken, ...

  21. 2017.solutions Manual For 'Modern Organic Synthesis. An ...

    2017.Solutions Manual for 'Modern Organic Synthesis. An Introduction' by Michael H. Nantz.pdf - Free ebook download as PDF File (.pdf) or read book online for free. Scribd is the world's largest social reading and publishing site.

  22. Modern Organic Synthesis 1st Edition Textbook Solutions

    Unlike static PDF Modern Organic Synthesis 1st Edition solution manuals or printed answer keys, our experts show you how to solve each problem step-by-step. No need to wait for office hours or assignments to be graded to find out where you took a wrong turn. You can check your reasoning as you tackle a problem using our interactive solutions ...