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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.

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)

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

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)

SN1 Reactions

In contrast to SN2 reactions, SN1 reactions show little nucleophile selectivity; that is, when more than one nucleophile is present in the reaction medium, SN1 reactions show only a slight tendency to discriminate between weak and strong nucleophiles, whereas SN2 reactions show a marked tendency to discriminate. a. Provide an

Hydrolysis: Order of Reactivity Explanation

When the alkyl bromides (shown below) were subjected to hydrolysis in a mixture of ethanol and water (80% CH3CH2OH/20% H2O) at 55OC, the rates of the reaction showed the following order: (CH3)3CBr > CH3Br > CH3CH2Br > (CH3)2CHBr Provide an explanation for this order of reactivity.

Sn2 Reaction with Ethyl Bromide and Isobutyl Bromide

Although ethyl bromide and isobutyl bromide are both primary halides, ethyl bromide undergoes SN2 reaction more than 10 times faster than isobutyl bromide. When each compound is treated with a strong base/nucleophile (CH3CH2O-), isobutyl bromide gives a greater yield of elimination product than substituted products, whereas eth

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.