2-) You may have noticed that the "solvent of choice" for many organometallic compounds such as Grignard reagents is dried diethyl ether or tetrahydrofuran. Why do we use this type of solvents for Grignard reactions instead of ethyl acetate, or protic solvents such as ethanol?

2-) You may have noticed that the "solvent of choice" for many organometallic compounds such as Grignard reagents is dried diethyl ether or tetrahydrofuran. Why do we use this type of solvents for Grignard reactions instead of ethyl acetate, or protic solvents such as ethanol?

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

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.69P

See similar textbooks

Related questions

Q: Why we need step 3 before step 4? a. Because the nitro group increases the electrophilicity at the…

Q: A student wanted to know whether the greater proximity of the ucleophile to the C-2 carbon in the…

A: The reaction of HCl with 2-methyl-1,3-cyclohexadiene will form 1,2-addition product and 1,4-addition…

Q: The ozone problems are likewise best illustrated by means of synthesis. Here I'm going to provide a…

A: The alkene on treatment with ozone and then dimethylsulfide forms corresponding carbonyl compounds…

Q: Question 12 of 30 > 0/1 Propose an efficient synthesis for the following transformation: The…

Q: 2) When molecule 2 is treated with HBr and peroxide one major product is formed. Based off of the…

A: Alkene reacts with HBr in presence of peroxide to form alkyl bromide. In this reaction, the HBr…

Q: The two Grignard reactions and the reduction reaction below are all believed to have similar…

A: Reaction involving organic compounds are called organic reactions. Organic reactions are of…

Q: 1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl…

A: The synthetic methods for the preparation of ethyl-2-methylpropylether are as follows-

Q: Question 11 Indicate the appropriate order of reagents used in this transformation. CN O 1.…

A: R-MgBr is a general formula of Grignard's reagent. Where, R is any alkyl or aryl group. H3O+ is act…

Q: Provide the organometallic reagent that is needed to perform the transformation shown below. (Use…

A: The reaction given shows the formation of alcohol from ketone.The reagent which is required for the…

Q: The reaction below precedes via an E2 elimination versus an SN2 reaction. Circle all of the answers…

A: Elimination reaction are organic reaction where the certain functional group is lost to form…

Q: III. Which alkyl halide in each of the following pairs will react faster in an SN2 reaction with OH?…

A: The nucleophilic substitution reaction involves the removal of the leaving group with its bonding…

Q: Please explain the mechanism for the Replacement of OH by halogen in reaction with HCl or HBr (SN1…

Q: Which of these reactions are likely to produce both elimination and substitutionproducts?…

A: Given reaction, 3-bromo-3-methylpentane + NaOMe (Me = methyl, CH3)

Q: Why do we not see 1,2-hydride shift rearrangements (or 1,2-methyl shift rearrangements) for E2…

A: A reaction which involve removal of a molecule containing atoms or groups give at least one p bond…

Q: Explain the features of E1 reactions are worthy of note ?

A: Elimination reaction is a type of reaction is mainly used to transform saturated compounds (organic…

Q: Why do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major…

Q: 12) Using the conmmpounds in the box, propose a synthesis for compounds 40, 41 and 42. You can use…

A: Among the given reagents NaOH is a base, PCC and Na2Cr2O7 are oxidizing agents, H2SO4 is an acid, Mg…

Q: Would you expect acetate ion (CH3CO2 -) to be a better nucleophile in an SN2 reaction with an alkyl…

A: The SN2/E2 reaction of alkyl halide is with neutral nucleophile/base, the increasing polarity of the…

Q: Meso-butane-2,3-diol can be synthesized from acetylene through a multi-step procedure. Identify the…

Q: 1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl…

A: Synthesis of ethyl isobutyl ether using PBr3, SOCl2, and TsCl, NaOH, Na2SO4 etc and relative merits…

Q: For the dehydrobromination of 1-bromobutane, no bubbling in the collection tube was seen after…

A: Is possible that your base is contaminated, you can repeat the experiment with new potassium…

Q: 2. A limitation of the Friedel-Crafts alkylation reaction is that the presence of…

Q: a) If the following compound were to undergo an E2 elimination reaction, what would be the…

A: Given reaction:

Q: an instructor will demonstrate how quickly turpentine (paint thinner, a ~2:1 mixture of alpha and…

A: Given: (mix of Unimolecular Substitution and Elimination products)

Q: 5. Retrosynthesis. Suggest how the molecules mentioned below can be synthesized (give the reagents…

Q: Starting with 3,5-hexadiyn-1-ol, select reagents from the table below that should be used to…

A: The reagents are faigb i) protection with TBDMS-Cl ii) deprotonation of terminal alkynes iii)…

Q: Account for complete retention of configuration in the solvolysis of (1).

Q: 1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl…

A: An ether group contains two alkyl or aryl or combination of alkyl and aryl group joined together by…

Q: SN2 Reaction lodide ion is an effective nucleophile in S2 displacements. In acetone solution, other…

A: Above reaction is 2° R-X.

Q: 1.Show the Elimination reaction of 2-bromopentane. 2.What contributed to formation of minor and…

A: Given reacion, Elimination reaction of 2-bromopentane.

Q: он COH Br

A: Aromatic compound can generally involve in electrophilic or nucleophilic substitution reaction based…

Q: 4. Study the curved arrows in the reactions below and provide the structures of the product(s)…

Q: In the chemical reaction between 1-Bromobutane and ethanolic silver nitrate solution, a precipitate…

Q: 2) Write a detailed mechanism for the following reaction: H2SO4 CH;CH,C=CH + H2O CH;CH,CCH3

A: Hydration reaction of Alkyne takes place in acidic medium as follows:

Q: How does changing the solvent from DMSO to CH3OH affect the rate of an E1 reaction?

A: E1 reaction stands for unimolecular elimination reaction. As the name suggests these reactions…

Q: Design a two step synthesis that converts 3-pentanone into 3'-pentyl acetate as shown below. H2 H2…

A: In the given sysnthesis the 3-pentanone is converted into 3-pentyl acetate. The synthesis done in…

Q: Propose a mechanism for the entire reaction of pent-1-yne with 2 moles of HBr. Show why…

A: On addition of HBr to an alkene or alkyne, the π-electrons attacks the proton in HBr and a…

Q: CH2 H3C OSO2CF3 С. CF3CO2H O-H `CH3 CF3- CF3SO3 + `CH3 a nonnucleophilic polar solvent O-H

A: Mechanism for the following reaction is

Q: (S)-2-Butanol, instead of (R)-2-butanol, is obtained from the reaction between (R)-2-bromobutane…

A: This is called SN2 Reaction in which inversion of configuration takes place.

Q: 2. Ordinary primary alkyl halides do not undergo SN1 reactions. However, the following two alkyl…

A: Those reactions in which a stable carbocation is formed after leaving of leaving group, will…

Q: Using the Grignard reagent selected above, provide a synthesis of the target molecule from…

A: In this we have to increase the carbon chain first .

Q: What are the mechanisms to getting to these 2 products?

A: Mechanism of following reaction is

Q: Choose the best set of reagents listed below to effect the chemical conversion shown in the box: R1…

Q: 5. Retrosynthesis. Suggest how the molecules mentioned below can be synthesized (give the reagents…

Q: Perform a retrosynthetic analysis by working backwards two steps in the synthesis below. Identify…

A: Given target molecule is alkyl halide.

Q: CH3 CH3 СООН СООН NO2 ŠO3H ŠO3H Identify the reagents represented by the letters in the above…

A: Reaction involved following concepts 1) Fridel crafts alkylation 2) sulphonation 3) oxidation of…

Q: 1. Excess LIAIH4 MeO НО 2. H2о

A: Given reaction: We have to write the mechanism of the reaction.

Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

2-) You may have noticed that the "solvent of choice" for many organometallic compounds such as
Grignard reagents is dried diethyl ether or tetrahydrofuran. Why do we use this type of solvents for
Grignard reactions instead of ethyl acetate. or protic solvents such as ethanol?

Expert Solution

This question has been solved!

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

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1rgan

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps

SEE SOLUTION Check out a sample Q&A here

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

Provide the reagents for the short syntheses (about 3-4 steps).
A student wants to choose the best solvent for organometallic compounds such as Grignard reagents. Based on the three solvents below, explain which is the best solvent for Grignard reagents. (You must also explain why the others are not suitable). (c) `O-H ether ethanol ethyl acetate
1. What is the function of CH»Ch in the bromination reactions? Why can it fulfil this role? 2. In not more than three (3) sentences, explain why terminal alkynes are acidic. 3. What impurities are removed when acetylene gas is made to pass through an acidified solution of CuSO:? 4. Explain the difference in the rate of free radical bromination reactions of toluene and cyclohexane. 5. Give the reagent er chemical cempounde, Previde only Ehe reasents nu Would differentiate tefel
This is a multistep syntheses. More than one reagent/reaction will be necessary to produce the product. Provide all necessary reaction conditions (HBr, HgSO4, etc.) and the products produced after each step of the synthesis.
The following reaction involves two sequential Heck reactions. Draw structural formu- las for each organopalladium intermediate formed in the sequence and show how the final product is formed. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of H and I from the starting material. Acetonitrile, CH,CN, is the solvent. 1% mol Pd(OAc), 4% mol Ph,P CH,CN C4H171 C4H16
Why should you keep your head out of the fume hood during the reaction between tetraphylcyclopentadienone and Dimethyl acetylenedicarboxylate? Because the addition of heat to this experiment increases the pressure within the reaction vessel, the apparatus could explode unexpectedly. O Due to the formation of carbon monoxide gas, which is toxic if inhaled. Due to the formation of carbon monoxide, carbon dioxide, and ethylene gas, which are all toxic when inhaled. O All of the above
organolithium reagents are strong bases. Because of this, they cannot be prepared from compounds that contain acidic groups (-OH, -NH:, -NHR, -SH, -C=CH, RCO:H) or compounds that have carbonyl groups. Which of the given syntheses of a Grignard reagent below would fail to form as written? Circle the answer and explain your choice Br Mg, ether MgBr 1) Mg, ether Mgl 2) Br Mg. ether MgBr 3) но но 2. Predict the major products for the following reactions with the correct stereochemistry were necessary. SOCI, LOH OH OH SOCI NBS ight NBS G light Me (CH, Cel Br MgBr
Starting with ethene give a suitable reaction scheme to convert it into Ethyl ethanoate in 4 steps
Nucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure via resonance. For the reaction below, draw the structure of the stabilized reaction intermediate in the box below. CI F3C CF3 NO₂ F3C N CF3 NO₂ • You do not have to consider stereochemistry. • Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than one resonance structure is possible, only draw the most important one.
1. What is the function of CH2Cl2 in the bromination reactions? Why can it fulfill this role?2. In not more than three (3) sentences, explain why terminal alkynes are acidic.3. What impurities are removed when acetylene gas is made to pass through an acidified solution of CuSO4?4. Explain the difference in the rate of free-radical bromination reactions of toluene and cyclohexane.5. Give the reagent or chemical test that would differentiate the following pairs o fcompounds. Provide only the reagents or chemical tests discussed in the module. Write chemical equations for the reactions involved. a. benzene and ethylbenzeneb. 1-butyne and 2-butynec. 2-methylpentane and 2-methyl-2-pentened. toluene and 1-methylcyclohexene
Help ASAP Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Do this by writing all the possible resonance forms for methoxybenzene, including the hybrid. Based on your structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack; (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.
Br2, H3O+ གོ་ཤི་ན་ཤི་ H3C CH3 CH3 CH3 Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br2, or 12, under acidic conditions. Using Br2 under acidic conditions, an intermediate enol is formed which adds bromine at the a-position. The reaction stops after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen, making the protonation less favorable. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :OH :OH Br-Br H3C H3C. Br Br CH₂ H₂ H3C CH3 H3C CH3 2b