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Organic Reaction Intermediates and Mechanisms

Reaction Mechanism

Predict the two most likely products for the following reaction and show a stepwise mechanism for the formation of each product. (Hint: one product is formed by Markovnikov addition, the other by a carbocation rearragement.) (CH3)3CCH=CH2 + HCl ->

Bridged Cyclic Compounds and SN2 Reactions

Bridged cyclic compounds like the ones shown in the attached .jpg are extremely unreactive in SN2 reactions. 1) Give a reason which will explain this. 2) How can you explain the fact that compounds of this type are also less reactive in the SN1 reaction than similar noncyclic compounds? (See attached file for full pro

Reaction of (R)-2-bromo-1-flourobutane with Sodium Cyanide in Ethanol (aq)

Pure (R)-2-bromo-1-flourobutane reacts with sodium cyanide in aqueous ethanol to form pure (R)-2-flouromethylbutanenitrile. 1) What is the probable mechanism of this reaction? Explain your reasoning. 2) Based on your choice of mechanism, explain how both the substrate and the product can have R configuration? 3) Wha

Drawing Chemical Products

Treatment of (2S, 3S)-2-bromo-3-phenylpentane with KOH can lead to different products, depending on the reaction pathway. Draw (2S, 3S)-2-bromo-3-phenylpentane and the major product(s) expected for each of the following reaction mechanisms: SN1, SN2. Please indicate the stereochemistry and regiochemistry clearly.

Design an Experiment with Elimination of Secondary Halide

I need help designing an experiment using a secondary halide, 2-bromohexane or 2-bromoheptane as the beginning material. I know that the things I need to do are use NaOH, -OH, and CH3OH to come up with the products of an alkene and secondary alcohol. I need specific reactions, materials, and procedures. I then plan to use GC/

Predict the Structure

Predict the structure of the diphenylquinone product, C28H40O2 by the oxidative coupling of 2,6-di-tert-butylphenol with oxygen in the presence of base. (Show work)

Isoprene reaction

Isoprene (2-methyl-1,3-butadiene) reacts with the following: (1) hydrogen chloride (1 mole equivalent) in ether (2) deuterium chloride (1 mole equivalent) in ether (3) bromine (1 mole equivalent) in carbon tetrachloride (4) excess hydrogen gas in the presence of a PtO2 catalyst (5) excess mercury (II) acetate and methanol f

Three compounds A, B and C all have the formula C5H10.

Three compounds A, B and C all have the formula C5H10. A and B rapidly decolourise bromine dissolved in CH2CL2 but compound C is unreactive. Compound A reacts rapidly with acidified water and a tertiary alcohol D is formed; however compound B yields a secondary alcohol. (a) Draw a possible structure for each of A, B and C.


Give a detailed mechanism for the reaction that occurs when ethyl methylmalonate CH3-CH(C=OOC2H5)2, acetone and 2-chloroacrylonitrile (CH2=CClCN) react in the presence of a base, to yield an epoxy compound CH3-C(EtOOC)2-CH2-C(NC)-O-C(CH3)2

Mechanism Reaction

Give a detailed mechanism for conversion of 2,7-dimethyl-2,6-octadiene, using H3PO4, into 1,1-dimethyl-2-isopropenylcyclopentane.

Alkene and Alkyne Mechanisms

In my organic class we are studying alkenes and alkynes. I am familiar with the addition and elimination procedures. However, I am unclear of how some of the mechanism go since my book only deals with the straight forward mechanisms such as halogenation, hydration, etc. Please see the attachment.

Mechanism & Reducing agent

When amide X is treated with lithium aluminum hydride, the corresponding amine can be isolated in good yield. (a) Provide a concise mechanism for this reaction. (b) Draw the structure of a reducing agent capable of converting an ester to the corresponding aldehyde. Give an explanation as to how this reagent works.

Synthesize a Compound

Synthesize the following compound from the indicated starting material. You may use: - any organic compounds containing three or less carbon atoms - benzene - n-bromosuccimide - triphenylphosphine - MCPBA - methylvinyl ketone - LDA, ethyl acetoacetate - diethyl malonate - wittig reagents - and any inorganic rea

Esters and Aldehydes

(1) Provide a detailed mechanism for reaction 1 and explain why it takes place. (2) Draw the structure of a reducing agent capable of converting an ester to the corresponding aldehyde. Explain in some detail how this reaction works.

Reaction Mechanism: Epoxide and Alcohol

Question: What is the mechanism for the following reaction? Please indicate the stereochemistry and electron transfer mechanism? Also, what kind of compound is the initial reactant and the final product? (Is it an epoxide?) Please see the attached file for the compound diagrams.

Reaction Involving Alcohol

Question: What are the products of these reactions, please include the stereochemistry. - What kind of compound is 1 and 2? (Please show electron transfer as well). Please refer to the attached file to the compound diagrams.