ORGANIC CHEMISTRY LL >BI<
null Edition
ISBN: 9781260561609
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 15.8, Problem 6P
Interpretation Introduction
Interpretation:
The reasonable structures for the two products obtained in the reaction of
Concept Introduction:
Methylene transfer from iodomethylzinc iodide to alkene is called the Simmon-Smith reaction. In the overall reaction, an alkene is converted to cyclopropanes.
This reaction is highly stereospecific and the addition of the methylene unit to the double bond is syn.
Substituents that were trans in
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Suggest an explanation for the fact that the order of reactivity of the halides toward n-butylbrosylate in acetone is Cl” > Br” > I~ when (C4H9)4N* is the cation of the halide salt butI” > Br” > Cl” when Li’ is the cation
Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination.
Conversion of an alkene to a halohydrin and internal displacement of a halide ion by an alkoxide ion are both stereoselective. Use this information to demonstrate that the configuration of the alkene is preserved in the epoxide. As an illustration, show that reaction of cis-2-butene by this two-step sequence gives cis-2,3- dimethyloxirane (cis-2-butene oxide).
Chapter 15 Solutions
ORGANIC CHEMISTRY LL >BI<
Ch. 15.1 - Each of the following organometallic reagents will...Ch. 15.3 - Write equations showing how you could prepare...Ch. 15.4 - Lithium diisopropylamide is often used as a strong...Ch. 15.5 - Write the structure of the organic product of each...Ch. 15.7 - Prob. 5PCh. 15.8 - Prob. 6PCh. 15.9 - Prob. 7PCh. 15.9 - Like nickel, iron reacts with carbon monoxide to...Ch. 15.9 - Prob. 9PCh. 15.9 - What is the oxidation state of manganese in the...
Ch. 15.9 - Prob. 11PCh. 15.10 - Prob. 12PCh. 15.10 - Prob. 13PCh. 15.11 - Give the structure including stereochemistry of...Ch. 15.11 - Prob. 15PCh. 15.12 - Homogeneous catalytic hydrogenation of the...Ch. 15.12 - Prob. 17PCh. 15.13 - What alkenes are formed from 2-pentene by olefin...Ch. 15.13 - The product of the following reaction was isolated...Ch. 15 - Suggest appropriate methods for preparing each of...Ch. 15 - Prob. 21PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 23PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 25PCh. 15 - A different stereoisomer of...Ch. 15 - Prob. 27PCh. 15 - Using phenyllithium and any necessary organic or...Ch. 15 - Prob. 29PCh. 15 - A number of drugs are prepared by reactions in...Ch. 15 - The following conversion was carried out in two...Ch. 15 - Outline syntheses of (a)...Ch. 15 - (S)-(+)-Ibuprofen can be prepared by...Ch. 15 - Like other hydroborations, the reaction of alkynes...Ch. 15 - The sex attractant of the female silkworm has been...Ch. 15 - Prob. 36PCh. 15 - (a) Exaltolide, a musk substance, has been...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and (Cyclobutadiene)tricarbonyliron...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...
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
- When N-bromosuccinimide is added to hex-1-ene in CCl4 and a sunlamp is shone on themixture, three products result.(a) Give the structures of these three productsarrow_forwardBirch reduction of 2-methoxynaphthalene gave a mixture of two isomeric compounds, each having the molecular formula C11H14O. Suggest reasonable structures for these compounds.arrow_forward1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with(a) buta-1,3-dienearrow_forward
- An organic was subjected to sodium fusion and the resulting Lassaigne’s extract boiled with FeSO4 and acidified with concentrated H2SO4, yielding a Prussian blue color. Give an example of a compound fits this description?arrow_forwardFriedel–Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.arrow_forwardElectrophilic nitration of benzoic acid gives almost exclusively 3-nitrobenzoic acid. By drawing the appropriate resonance forms of the intermediate cations resulting from attack of [NO2]+, explain this result.arrow_forward
- One step in the synthesis of dodecahedrane involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.arrow_forwardPropose two sets of reagents that might be combined in a Wittig reaction to give the indicated Z alkenearrow_forwardA certain hydrocarbon, C7H10, yields the two products shown below upon oxidative cleavage with KMnO4/H3O+ . Deduce the structure of the hydrocarbon.arrow_forward
- Outline the synthesis of 1-bromo-2-methylpropane by using suitable alkenearrow_forwardLike other hydroborations, the reaction of alkynes with catecholborane is a syn addition and its regioselectivity is opposite to Markovnikov’s rule.Use this fact to outline a synthesis of the compound shown from 1-hexyne and (Z)-C6H5CH=CHBr.arrow_forwardwe know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning