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
Textbook Question
Chapter 7, Problem 26PP
Practice Problem 7.26
(a) Devise retrosynthetic schemes for all conceivable alkynide anion alkylation syntheses of the insect pheromones undecane and 2-methylhepcadecane (see “The Chemistry of … Pheromones” box in Chapter 4).
(b) Write reactions for two feasible syntheses of each pheromone.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Suggest reactivity of compound A, B and C in increasing order of E2 reaction
A student was given from the list of the compounds below A, B and D blindly and asked to identify them all. He treated each of them with Brady's reagent (2,4-ditrophenylhydrazine) and isolated a bright yellow compound for one of them, but the other two gave false negatives. The student reasoned that the false negatives may be due to sterics and, on further thinking, it dawned on him that he might be able to rule out one of the false negatives with the haloform test. What compound did he find compatible with the haloform test? That compound did indeed give a false negative in the Brady test. Which of the other two was positive in the Brady test?
A = haloform
B = Brady
A = haloform
D = Brady
B = haloform
A = Brady
B = haloform
D = Brady
D = haloform
A = Brady
D = haloform
B = Brady
3) Outline an acceptable step by step mechanism for the Nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine. Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge.
Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Prob. 1PPCh. 7 - Prob. 2PPCh. 7 - Prob. 3PPCh. 7 - Prob. 4PPCh. 7 - Practice Problem 7.5
How many stereoisomers are...Ch. 7 - Prob. 6PPCh. 7 - Prob. 7PPCh. 7 - PRACTICE PROBLEM 7.8
Examine Solved Problem 7.3....Ch. 7 - Prob. 9PPCh. 7 - Practice Problem 7.10 When...
Ch. 7 - Practice Problem 7.11
(a) When...Ch. 7 - Prob. 12PPCh. 7 - Prob. 13PPCh. 7 - Practice Problem 7.14
Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15
Rank the following alcohols...Ch. 7 - Practice Problem 7.16
Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 18PPCh. 7 - Prob. 19PPCh. 7 - Practice Problem 7.20
Show how you might...Ch. 7 - Prob. 21PPCh. 7 - Prob. 22PPCh. 7 - Practice Problem 7.23
Write the structure of...Ch. 7 - Prob. 24PPCh. 7 - Prob. 25PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 28PCh. 7 - Prob. 29PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.36. Explain the following observations: When...Ch. 7 - Prob. 37PCh. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 39PPCh. 7 - Prob. 40PPCh. 7 - Prob. 41PPCh. 7 - Prob. 42PPCh. 7 - Your task is to prepare isopropyl methyl ether by...Ch. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Prob. 46PCh. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Prob. 48PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 53PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - cis-4-Bromocyclohexanol tBuOHtBuO racemic C6H10O...Ch. 7 - Prob. 59PPCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 61PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 63PCh. 7 - Prob. 64PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGP
Additional Science Textbook Solutions
Find more solutions based on key concepts
a. How can aspirin be synthesized from benzene? b. Ibuprofen is the active ingredient in pain relievers such as...
Organic Chemistry (8th Edition)
Q4. Which property of rubbing alcohol is a chemical property?
a) Density (0.786 g/cm3)
b) Flammability
c) Bo...
Chemistry: A Molecular Approach (4th Edition)
4. 38 Strontium has four naturally occurring isotopes, with mass numbers 84, 86, 87, arid 88.
a. Write the atom...
Basic Chemistry (5th Edition)
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
33. Consider the reaction:
The tabulated data were collected for the concentration of C4H8 as a function...
Chemistry: Structure and Properties
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
- Give the reagents and conditions necessary for the following conversion. A to B, B to D, B to C, B to E, E to F, E to G, G to H, H to I. Hence deduce the name and structural formula of the compounds C and I. Compare the procedure for converting F and E to G.arrow_forwardGiven the sequence of reactions shown below assume the reactions are stoichiometric fill in the reagents needed for steps A B and C and explain what happens in each step of the reactions, by also namearrow_forwardWrite down the explicit structures of A, B, C and D in accordance with the reactions given in the synthesis plan, which shows the synthesis of D, a pheromone of moth.arrow_forward
- Starting with acid chloride with exactly 5 carbon atoms, and using appropriate reagents outline the synthesis of the following molecules:arrow_forwardWhen the nitrogen-containing aromatic heterocyclic compounds 1 and 2 are treated with HCl, only 1 forms the hydrochloride salt, whereas compound 2 is unreactive. Provide an explanation for this observed reactivity.arrow_forwardDescribe a synthetic plan with suitable justification of the sequence of reactions you would understate to complete synthesis of compound 1 from compounds 2,3,4. Suggest suitable reagentsarrow_forward
- Give the structure of compound 1 and compound 2arrow_forwardAlthough useful in agriculture as a soil fumigant, methyl bromide is an ozone-depleting chemical, and its production is being phased out. The industrial preparation of methyl bromide is from methanol, by reaction with hydrogen bromide. Write a mechanism for this reaction and classify it as SN1 or SN2.arrow_forwardCompound A, C3H7Br, does not react with cold dilute potassium permanganate solution. Upon treatment with potassium hydroxide in ethanol, A gives only product B, C3H6. Unlike A, B decolourises potassium permanganate solution. Ozonolysis of Bgives C, C2H4O, and D, CH2O. Suggest the structural formulae of A, B, C and D.Write the equations for all the reactions involved.arrow_forward
- The sex attractant of the female housefly (Musca domestica) is called muscalure, and its structure follows. Outline a synthesis of muscalure, using the Wittig reaction. Will your synthesis lead to the required cis isomer?arrow_forwardDraw/outline a reasonable and detailed mechanism for the dehydration of 2-methylcyclohexanol catalyzed by phosphoric acid. Use curved arrows to show the flow of electrons and draw the structures of all intermediates and byproducts formed in the reaction. Predict and rationalize the expected product distribution based on thermodynamic aspectsarrow_forwardExplain the differences in acidity between p-cyanobenzoic acid and m-cyanobenzoic acid. Illustrate your answer appropriately, showing the acid-base reaction that takes place with each of these and explaining in such terms as electronic (inductive or resonance) and/or steric effects.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY