Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 20, Problem 51P
Develop a synthesis for the following molecule using only the indicated materials as sources for the carbon atoms that appear in the final product. As a hint, you will need to draw upon several reactions from earlier chapters to come up with a successful solution, and you may have to use some of the carbon sources more than one time. Also assume that
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
10. Propose a synthesis for the following molecule from starting material/reagents
containing 6 carbons or less. Be sure to show all reagents and synthetic intermediates in
your answer. You do not need to show reaction mechanisms.
ОН
Br
. Please provide a forward synthesis for the following aromatic compounds using benzene as the starting material for all of your
syntheses. In some cases, you might run a reaction that produces two products. This outcome is fine; just draw both products,
and indicate that you will separate them, and then proceed forward with the compound needed.
Br
HO2C,
Br
CI
Convert 2-pentanol into 2,3-dibromopentane. Draw structures of the starting material (2-pentanol) and final product
(2,3-dibromopentane), and show the two reactions needed for this synthesis. Include the structure of the intermediate
compound, and the reagents and conditions for each reaction. Then explain why 1,2-dibromopentane would not be a
significant product of this synthesis.
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 1PPCh. 20 - Prob. 2PPCh. 20 - Practice Problem 20.3
Write a mechanism that...Ch. 20 - Prob. 4PPCh. 20 - PRACTICE PROBLEM 20.5 Outline a preparation of...Ch. 20 - Prob. 6PPCh. 20 - Prob. 7PPCh. 20 - Prob. 8PPCh. 20 - Prob. 9PPCh. 20 - Prob. 10PP
Ch. 20 - Practice Problem 20.11 In the preceding examples...Ch. 20 - Prob. 12PPCh. 20 - Prob. 13PPCh. 20 - Practice Problem 20.14
Outline a synthesis of...Ch. 20 - Prob. 15PPCh. 20 - Prob. 16PPCh. 20 - Prob. 17PPCh. 20 - Prob. 18PPCh. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - 20.28 What products would you expect to be formed...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - Explain the following, including mention of key...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W:
Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - For each of the following, identify the product...Ch. 20 - 20.51 Develop a synthesis for the following...Ch. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 53PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 56P
Additional Science Textbook Solutions
Find more solutions based on key concepts
49. For the reaction shown, calculate the theoretical yield of product in moles for each of the initial quantit...
Introductory Chemistry (5th Edition) (Standalone Book)
Give Lewis dot structures and sketch the shapes of the following: a. SeCl4 b. l3- c. PSCI3 (P is central) d. lF...
Inorganic Chemistry
Show that, for water at 1-atm pressure with TsTsat=10C , the Jakob number is much less than unity. What is the ...
Fundamentals of Heat and Mass Transfer
The NF bond is more polar than the NH bond: but NF3 has a smaller dipole moment than NH3. Explain this curious ...
Organic Chemistry (9th Edition)
61. What is the pH of a solution in which 224 mL of HCl(g), measured at 27.2 °C and 1.02 atm, is dissolved in 1...
Chemistry: A Molecular Approach (4th Edition)
Identify whether each of the following compounds could be made with a Gabriel synthesis:
Organic Chemistry As a Second Language: Second Semester Topics
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Starting with benzene and using any other reagents of your choice, design a synthesis for the following compound: Br XX O₂N The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A HNO3, H₂SO4 D Fuming H₂SO4 B E Br2, AlBr3 Dilute H₂SO4 C BrMg F MgBr axxa. AICI 3arrow_forwardPropose a synthesis for the following molecule starting from benzene. Be sure to show all necessary reagents and the intermediates after each reaction. You do not need to show reaction mechanisms.arrow_forwardStarting with benzene and using any other reagents of your choice, design a synthesis for the following compound: The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A OEt 1) EtMgBr 2) H₂O* D NaOEt, heat B HNO3, H₂SO4 E NaOH, heat с F Cl₂, AICI3 CH3CH₂COCI, AICIarrow_forward
- Propose a synthesis for the following molecule from starting material/reagents containing 6 carbons or less. Be sure to show all reagents and synthetic intermediates in your answer. You do not need to show reaction mechanisms.arrow_forwardStarting with benzene and using any other reagents of your choice, design a synthesis for the following compound: COOH NO₂ COOH The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A Mel, AlCl3 B KMnO4, NaOH, heat (followed by H3O+ workup) C HCI, Zn D E F (CH3)2CHCI, AICI 3 HNO3, H2SO4 Fuming H2SO4arrow_forwardWrite four examples of the condensation reactions of carbonyl compounds, starting with benzaldehyde (C6H5CHO), with appropriate reagents and appropriate reactions. Write down the mechanism of one you want in detail.arrow_forward
- Starting from acetylene and alkyl halides not longer than 4 carbon atoms, show the synthesis of 3-octanol and a ketone. Indicate the reagents in each step. You may use more than one mole of the reactants.arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forward10. Propose a multi-step synthesis to prepare para-nitrotoluene from benzene. NOTE: You can just provide the description or name of the reaction, you do not have to provide the actual reagents.arrow_forward
- You are a chemistry company's latest chemistry recruit and your first job is to prepare 2-methylcyclohexanol. The one key starting material you have been given is methylcyclohexane. Draw a scheme to take you from the starting material to the product outlining the reagents you would use for each step as well as the key organic product(s) formed from each step. [Note: You do not need to show mechanisms for any steps]arrow_forwardShow how to synthesize the following product as the major product starting with 2,2-dimethylpropane as the starting material. You may use additional reagents and any number of steps. Be sure to list each step with all reactants/reagents/conditions required. (Do not use hydrogenation reactions). Write the process.arrow_forwardIn attempting to make 2-bromo-2-methyl-propane from 2-methyl-propene, as shown below, you used a dilute aqueous solution of hydrobromic acid. Upon analysis of the isolated product, you realize there is a major unwanted by-product. Br a) Based on the reaction conditions used, predict the major by-product and show a mechanism for its formation. b) What should be changed in the reaction conditions described in order to completely avoid the formation of the unwanted by-product?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY