Triethyloxonium tetrafluoroborate, (CH3CH2)3O+ BF4 −, is a solid with melting point 91–92 °C. Show how this reagent can transfer an ethyl group to a nucleophile (Nuc:−) in an SN2 reaction. What is the leaving group? Why might this reagent be preferred to using an ethyl halide?

Triethyloxonium tetrafluoroborate, (CH3CH2)3O+ BF4 −, is a solid with melting point 91–92 °C. Show how this reagent can transfer an ethyl group to a nucleophile (Nuc:−) in an SN2 reaction. What is the leaving group? Why might this reagent be preferred to using an ethyl halide?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter3: Stereoisomerism And Chirality

Section: Chapter Questions

Problem 3.39P

See similar textbooks

Related questions

Q: Predict the product formed in the nucleophilic aromatic substitution reaction between…

Q: Predict the starting material or reagents needed to carry out the desired reactions

A: Three questions based on reactions of alkyne, reactions of alkene and reactions of carboxylic acids.…

Q: Choose the best reagents from the list provided below for carrying out the following conversion.…

Q: What reagents are needed to carry out this reaction? CH;CH,CH,CCH PCC in methylene chloride Sia2BH…

A: We will first determine the reagent for the conversion of above organic reaction then we will…

Q: Give the products of the following substitution reactions. For every reaction, show electron pairs…

A: Given : We have to make the substituted products for the given reactions.

Q: Rank the nucleophiles in following group in order of increasing nucleophilicity. H2O, −OH, CH3CO2-

A: Water is a weak nucleophile because it is neutral. Since acetic acid is more acidic than water, the…

Q: Draw the products of each Lewis acid-base reaction. Label the electrophile and nucleophile. CH3 CH3…

A: In an organic reaction, the electrophile is a species that lacks electrons. It is an…

Q: OH OH Phph Ph CrO3 H₂SO4 SOCI₂ een H HN(CH,CH3)2

Q: Br Br2 CH3 CH3 H3C° CH2Cl2 H3C Br Electrophilic addition of bromine, Br2, to alkenes yields a…

A: Alkene are reactive in nature due to unsaturation

Q: 4. S'Na* acetone 5. Br CH3C=CLi* DMSO

A: 4. Secondary alkyl iodide and strong nucleophile prefers sn2 reaction. 5. Primary alkyl bromide and…

Q: xx-00 CI Br NH₂ NH

A: An arrow always depicts from a region of high electron density to low electron density ; that is…

Q: Give a mechanism that accounts for the organic products of this reaction. Your mechanism must…

A: In SN2 reaction there is inversion in configuration. This is because nucleophile attacks from the…

Q: OH + H20 1.CHзMgBr 1. CHзONa CH3OH CH3OH H2SO4 2. Н2о 2. H20 H2SO4 I II III IV V

Q: following

Q: A student wanted to try to make phenoxyacetic acid using hydroxyacetic acid (HOCH2COOH) and…

A: Phenoxyacetic acid can be prepared by using hydroxyacetic acid (HOCH2COOH) and NaH. Strong base NaH…

Q: Provide the missing reactants, reagents, or products for the following reaction sequences

Q: Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in…

A: Given that, a reaction scheme is We have to draw the mechanism for the formation of the ethyl…

Q: When propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and…

A: Alkene gives an electrophilic addition reaction with hydrogen halide to form an alkyl halide.

Q: Show how to carry out the transformation of benzene to chlorobenzene by going through a diazonium…

Q: Which of the following is more nucleophilic and why? CH30 (CH3)3CO 1 2 Compound 2, because its…

A: Strong nucleophile means an atom or a group carry lone pair of electrons. It effectively go to…

Q: Using Ethylene, C2H4, and methyl bromide, CH3Br, as your sole sources of carbon, propose a synthesis…

A: The objective of this question is to propose a synthesis for t-BuOH ((CH3)3COH) using Ethylene…

Q: In an SN2 reaction between 2-chlorobutane and iodide ion, what happens to the rate of the reaction…

A: Reaction between 2-chlorobutane and iodide ion is 2nd Order. Rate of 2nd Order reaction on both…

Q: Many hunting dogs enjoy standing nose-to-nose with a skunk while barking furiously, oblivious to the…

A: Using the chemical reactions how the mixture helps to remove the skunk spray from the dog has to be…

Q: 1. Cl₂, H₂O 2. NaOH Another mechanism for the formation of epoxides is through the formation of a…

A: An arrow always depicts from a region of high electron density to low electron density ; that is…

Q: The following reaction involves two sequential Heck reactions. Draw structural formu- las for each…

A: Given reaction,

Q: 1) Nucleophilic substitution reaction of alkyl halide is a process when nucleophile replace the…

A: It is an example of Nucleophilic substitution reaction. There are two types of Nucleophilic…

Q: Predict the product formed in the nucleophilic aromatic substitution reaction between…

Q: 1. Br₂, PBг3 2. H₂O H3C OH в незв H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic…

A: It is the Hell-Volhard-Zelinsky reaction.Activation: The carboxylic acid is activated by treatment…

Q: The SN2 reaction is an example of a nucleophilic substitution reaction. Draw the structure of the…

A: Interpretation- As given here that SN2 reaction is an example of a nucleophilic substitution…

Q: An electron-deficient carbon atom reacts with a nucleophile, symbolized as: Nu−. Define this ?

A: To define the below statement:An electron-deficient carbon atom reacts with a nucleophile,…

Question

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Protection of Groups in Organic Synthesis

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

Predict the product formed in the nucleophilic aromatic substitution reaction between 1-chloro-2,4-dinitrobenzene and sodium methoxide (NaOCH3). Draw the mechanism for the reaction, showing why the product you have selected is formed.
Nitration of an aromatic ring involves an electrophilic substitution reaction. Draw the structure of the electrophile that is attacked by the aromatic ring and the intermediate formed after attachment of the electrophile to the ring. Be sure to show formal charges.
Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*
Show how to carry out the transformation of benzene to chlorobenzene by going through a diazonium intermediate. At each step, either select the appropriate reagents or draw the correct product. NH₂ HNO3 H₂SO4 product 1 reagent 2 NaNO₂ HCI product 3 reagent 4 CI
orgo chem questions
The product of this chloromethylation can be converted to piperonal, which is used in perfumery and in artificial cherry and vanilla flavors. How might the CH2Cl group of the chloromethylation product be converted to a CHO group?
Draw the energy diagram of the following reaction. Label and draw the reactants, intermediates, and products. Label the transition state of the rate limiting step and draw the transition state of the rate determining step. Is it a concerted or stepwise reaction? Write the rate law for this reaction. How do we increase the reaction rate? If we use deutrium-tert-butyl bromide such as (CD3)3CBr instead of (CH3)3CBr, will it increase or decrease the reaction rate, or is there no meaningful rate change? Write reasons for your answer. Draw mechanisms for reactions by drawing arrows and intermediates.
When propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.
Draw the products of each Lewis acid-base reaction. Label the electrophile and nucleophile. CH3 CH3 + H2SO4 CH3 CH3 + H20
Draw the organic product(s) you would expect from the following reaction. Assume products derive from the most stable carbocation intermediate(s).
Give me a clear handwritten answer
Define Nucleophilic Substitution of RCOZ (Z = Leaving Group) ?