Explore BrainMass

Organic Reaction Intermediates and Mechanisms

Organic Chemistry Reactions: Example Problems

Please see attached file for the properly formatted question. A reaction of a tertiary alkyl halide gives two products. Where do they come from (SN1, SN2, E1 or E2) processes? What are the mechanisms for these processes?

Which SN1 reaction is faster?

Which reaction is faster and what is the kinetics of these reactions? a) (CH3)3CCl ----> (CH3)3COH (in 70% water/methanol) b) (CH3)3CCl ----> (CH3)3COH (in 50% water/acetone) The faster reaction is shown and the kinetics are discussed.

Synthetic Pathway for Synthesis of 4-bromoacetanilide

Provide a reasonable synthetic pathway for the synthesis of 4-bromoacetanilide starting from benzene. Show the reagents necessary to accomplish each step and the structure of the intermediate products. Show only the reagents, not the mechanism. See attached file for full problem description.

D-glucose Isomers..

2. Turn the -OH on carbon 5 around so it is close to the aldehyde carbon (carbon #1). 3. Form the hemi-acetal using the carbon #5 -OH and the carbonyl at carbon 1. a. As you make the hemi-acetal, write out the mechanism by which this occurs. Concentrate your efforts on what is happening at C5 and C1. Review the formation of

Which reaction will proceed faster?

Please help with the following problem. For an SN2 reaction, the effect of solvent polarity is usually much less, but the ability (or really lack there of) of the solvent to solvate the nucleophile is the important criteria. Which of the two reactions proceed faster: a.) CH3CH2I in presence of ethanol or b.) CH3C

Aldol Condensation Reaction

Could you please give a stepwise mechanism for the preparation of 3-nitrochalcone from 3-nitrobenzaldehyde and acetophenone. (This is an aldol condensation reaction)

Mononitration of Compounds

Please find the mononitration product for the following (see attached file for diagrams). No mechanism is needed. (For part D the side chain should be COOC2H5 nots COOC2H2)

Preparing Compounds from Alkyl Halides

1. Suggest a method to prepare each of the attached compounds from alkyl halides (be specific on the alkyl halide used for each problem) 2. For each reaction suggested in #1, indicate whether it is SN2, SN1, E2, or E1.

Synthetic schemne for synthesis

(See attached file for full problem description) Complete the attached synthetic scheme by providing the reagents required for synthesis

Aldol Condensation Production of Pentaerythritol

The question reads: the compound pentaerythritol C(CH2OH)4 used in making explosives, is obtained from the reaction of acetalaldehyde and formaldehyde in the presence of Ca(OH)2. Outline the probable steps in the structure. --- I think I know the final outcome I am having trouble with the steps to get to the final structure. Rea

NMR Spectral Data

With NMR spectral data supplied I need to know the structure of product X and structure of product Y as well as mechanism by which product X is formed. (See attached file for full problem description)

Drawing and Naming Chemical Structures

2. A. Draw structures for the following compounds: 1-phenyl-1,2-epoxybutane, dimethylsulfide B. Name the following compounds: see attached file for diagrams. 3. Imagine that you have treated cis-2,3-epoxy-3-methylpentane with aqueous acid in a ring-opening reaction. a. Draw the epoxide, showing stereochemistry. b.

Dehydration of Methylcyclohexanol

What is the step by step mechanism for dehydration of 2-methylcyclohexanol so that the following products are obtained:3-methylcyclohexene (non-Zaitsev, E2), 1-methylcyclohexene (Zaitsev, E1), and methylenecyclohexene (hydride shift, minor product)? In addition, the 2-methylcyclohexanl exist in both cis and trans form. Pleas

Addition of bromine to 2-pentene

Write structure of dibromine products that you think will be formed as a result of the reaction of Z-2-Pentene with Bromine. How about the dibromide products predicted when E-2-Pentene reacts with Bromine.

Characteristics of Solvolysis Reactions

I need some help answering this question: Solvolysis reactions may be defined as reactions in which: a. Carbocations are required intermediates b. Elimination competes with substitution c. Reactivity is always accompanied by inversion of configuration d. The attacking nucleophile is usually the solvent e. Aprotic solvents

Converting Codeine to Morphine in the Body

Please help with the following problem. Writing a chemical equation for the conversion of Codeine to Morphine in the body. I know that the ether group of codeine becomes an alcohol group in the morphine, but I am unable to get a formula with the other products. I could also use some help with making sure I have the funct

Products of Organic Chemistry Reactions

I need help with showing the products for the following attached reactions problem. Please see attachment. Show the product(s) of the following reactions. Show stereochemistry where applicable.

SN1 and SN2 Mechanism

I need help writing the balanced equations for the attached problems and determining which reactions proceed by an SN1 mechanism and SN2 mechanism. --- 1. Write the balanced equations for the following: a. 2-bromobutane + NaI ---> b. 2-bromobutante + AgNO3 + EtOH ---> c. 2-bromo-2-methylpropane + NaI ---> d. 2-bromo-2-m

Reaction Mechanism - 1-butene-3-yne

I need help with writing the reaction and predict the major product for the following reactions. (Make sure to consider stereochemistry and regiochemistry, if applicable) a) 1-butene-3-yne reacts with excess hydrogen in the presence of a Pd/C catalyst b) 1-Butyne reacts with BH3 followed by hydrogen peroxide.

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 ->

Reaction Mechanism - Acetylene

Beginning with acetylene and using any other reagents necessary, how would you synthesize 1,2-dichloropropane? (Hint: more than one step is required. Show all reagents and all intermediate steps clearly.)

Treatment of (2R, 3S)-2-bromo-3-phenylpentane with KOH

Problem: Treatment of (2R, 3S)-2-bromo-3-phenylpentane with KOH can lead to different products, depending on the reaction pathway. Draw (2R, 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.

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