1.OHHBr2.H3C-O+H3C-O-LiLOH2Bra = Proton transferb = Lewis acid/based= E1 Eliminatione = E2 Eliminationf = SN1 Nucleophilic substitutiong= SN2 Nucleophilic substitutionC = Electrophilic additionThe rections above involve synthesis or reactions of alcohols and ethers.Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a -g for youranswers.1.2.Submit AnswerRetry Entire Group1 more group attempt remaining

1. In the first reaction the oxygen group of the cyclohexanol acts as a base and abstract the proton…

Answered: 1. OH HBr 2. H3C-O + H3C-O-Li LOH2 Br a…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

See similar textbooks

Similar questions

[Review Topics] [References] Br H3C CH3 H3C H3C 1. Aqueous ethanol + HO +] H. CH3 H. CH3 BH3 O-BH3 f=Sn1 Nucleophilic substitution g = Sn2 Nucleophilic substitution a = Proton transfer d = El Elimination b Lewis acid/base e = E2 Elimination c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - gf answers. 2.
[Review Topics] [References] HO pyridine 1. SOCIl, + sO2 + H. Aqueous acetone H3C H20 H3C HBr 2. Br H OH optically active racemic f = SN1 Nucleophilic substitution g = SN2 Nucleophilic substitution a = Proton transfer d = E1 Elimination b = Lewis acid/base e = E2 Elimination c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. 1. 2.
3- Write the organic product(s) and reaction mechanism a- b- CO₂H H3O heat CO₂CH3 1. NaOCH3 2. (CH3)2CHI 3. aq. NaOH 4. H₂O*, heat
CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:
Complete the following reactions by filling in any missing reactants, reagents or products. a) Zn(Hg) conc. HCl b) ОН ? с) ОН РСС CH,Cl,
In nucleophilic aromatic substitution reactions that proceed by the nucleophilic addition-elimination mechanism, the reaction rate increases as the electronegativity of the halogen leaving group increases: Ar-I < Ar-Br < Ar-CI < Ar-F. Which step does this suggest is the rate-determining step of the mechanism-the addition step or the elimination step? Explain.
An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.
Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution. bl || A. B. C. D. E. NH₂ مل I > IV > III > || || > ||| > IV >| | > ||| > || > IV III > IV> || > | IV > I > III > || IV
2. Complete the reactions, no mechanisms. Name each reaction. If no reaction occurs, write NR. a. b. C. d. yox за NaOt-Bu/t-BUOH NaOEVEtOH NaObu/BuOH NaOH, H₂O, heat H+
Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.
Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)
Claisen condensation between diethyl phthalate and ethyl acetate followed by saponifi- cation, acidification, and decarboxylation forms a diketone, C,H,O,. COOEt 1. EtO Na+ HCI, H,O B NaOH, H,O + CH3COOEt C,H,O2 2. НС, Н,О heat heat COOEt Diethyl phthalate Ethyl acetate Propose structural formulas for compounds A and B and the diketone.

SEE MORE QUESTIONS

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS