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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

The reaction of a compound with silver nitrate in ethanol is used as a chemical test to determine if the compound is an alkyl halide. The formation of a precipitate of the silver halide constitutes a
The reaction of an alkyl chloride (or bromide) with sodium iodide in acetone proceeds according to the following equation: Sodium iodide is soluble in acetone, whereas both sodium chloride and sodium
The Lucas test is used to check for the presence of an alcohol functional group in an unknown compound. The test reaction is shown in the following equation: Smaller alcohols are soluble in the
Explain why this secondary alcohol reacts with HCl and ZnCl2 in H2O at about the same rate as a primary alcohol (see Problem 8.38)
What reagent and solvent would you use to carry out the following transformations?
In most cases, RO ? cannot act as a leaving group in nucleophilic substitution reaction. Explain why the following reaction does occur:
Explain which of these reactions would have the faster rate:
Heating ethanol with sulfuric acid is one method used for the preparation of diethyl ether. Show all of the steps in the mechanism for this reaction:
When an aqueous solution of (R)-2-butanol is treated with a catalytic amount of sulfuric acid, slow racemization of the alcohol occurs. Show all of the steps in the mechanism for this process.
Show all of the steps in the mechanism and explain the stereo chemistry for this reaction:
Show both the substitution and elimination products that would be formed in these reactions:
The reaction of 3-iodo-2, 2-dimethylbutane with ethanol gives three elimination products in addition to two substitution products as shown in the following equation. Show all the steps in the
Show the structure of the carbocation that is observed when this compound is dissolved in superacid.
How much is the reaction rate for these reactions increased or decreased if the concentration of hydroxide ion is doubled? If the concentrations of the both the alkyl chloride and hydroxide ion
Show how these compounds could be prepared from alkylhalides:
Show how these products could be synthesized from the indicated starting material. More than one step may be necessary. Make sure that the product has the stereo chemistryshown.
Cyanide anion has two potential nucleophilic sites: the carbon and the nitrogen. Explain which site is expected to be the strongernucleophile.
This SN1 reaction gives the mixture of products shown. Show the structure of the carbocation formed in this reaction and explains what factor favors the reaction of the nucleophile at the primary
The rearrangements of both the 1-butyl and 2-butyl carbocations to the tert-butyl carbocation occur rapidly in super acid solution. Both of these rearrangements proceed through several steps and must
The two nitrogen of the following dipeptide have very different re-activities as nucleophiles explain which nitrogen is the betternucleophile.
Amino acids can be prepared (as their conjugate bases) by the reaction of a bromine substituted carboxylic acid with excess ammonia. (a) The conjugate base of the amino acid alanine is formed in the
Explain which of the two acetate esters, product 1 or product 2, is formed when the alkyl chloride is reacted with sodium acetate in DMSO. Problems using online three-dimensional molecular models
Explain which of the two methyl esters, product 1 or product 2, is formed when the alkyl chloride is heated in methanol. Problems using online three-dimensional molecular models
Explain which of these two alkyl chlorides reacts faster with sodium acetate in DMSO. Problems using online three-dimensional molecular models
Arrange these nucleophiles in order of decreasing rate of reaction with iodomethane and explain your answer. Problems using online three-dimensional molecular models
Show the elimination products of thesereactions:
Show the products, including stereo chemistry, of these eliminationreactions.
What product would be expected from the elimination reaction of (1R, 2S)-1-bromo-1, 2-dipheylpropane using sodium ethoxide in ethanol as the solvent?
Both cis and trans alkenes can be formed from this compound y anti elimination. Draw a Newman projection of the conformation required to form each of these products and, on the basis of these
Show the products of these eliminationreactions:
Explain why one of these compounds reacts readily by an E2 mechanism when treated with sodium ethoxide in ethanol but the other doesnot:
Show the products of these elimination reactions and indicate which ismajor:
The reaction of 2-bromobutane with ethoxide ion in ethanol gives 81% of a mixture of (Z)- and (E)-2-butene. Explain which stereo isomer you expect to predominate in this mixture.
Show the products of these reaction and indicate which ismajor:
Show the major products of these eliminationreactions:
When 2-methyl-2-propanol is treated with sulfuric acid, 2-methylpropene is formed. Show all of the steps in the mechanism for this reaction. Don't forget to use curved arrows to show the movement of
Show all of the steps in the mechanism for this reaction, what other products would you expect to beformed?
Show the products of thesereactions:
Show the products of thesereactions:
Show the substitution and/or elimination products for these reactions. Explain which mechanism are occurring and which product you expect to be the majorone.
Explain which mechanism is preferred in these reactions and show the majorproducts:
Explain which reaction mechanism (E1, SN1, E2, SN2) these reactions follow, and show the majorproducts:
Show all the steps in the mechanism for this reaction. What substitution product(s) would also be formed in thisreaction?
Show the products of this reaction. How would the composition of the products change if t-BuO? in t-BuOH were used in place of ethoxide ion in ethanol?
All of the stereo isomers of 1, 2, 3, 4, 5, 6-hexachlorocyclohexane have very similar rates of E2 reaction except the following stereo isomer, which reacts about 7000 times more slowly than the
Show the product of thisreaction:
Explain why the reaction of the cis-isomer of this compound with potassium tert-but oxide in tert-butanol is about 500 times faster than that of thetrans-isomer.
Explain which of these compounds has a faster rate of E2elimination:
Frequently, several different routes can potentially be used to synthesize a desired compound. For example, the following two routes can be envisioned for the preparation of cyclopentyl methyl ether.
What reagents and reaction conditions could be used to carry out the followingtransformations?
Suggest the best way to prepare these alkenes from alkylhalides.
When heated in ethanol, this alkyl halide gives two substitution and two elimination products. Show the structures of these products and the mechanism for theirformation.
Which of these stereo isomers has the faster rate of E2elimination?
Show the products of this elimination reaction and explain which ismajor:
Explain why deuterium is lost in preference to hydrogen in this Hofmann eliminationreaction:
Explain why this compound gives about 50%syn elimination whenheated:
When 2-bromo-2-methylbutane is heated in a mixture of ethanol and water, it gives a 64% yield of substitution products and a 36% yield of elimination products.(a) What mechanisms does this reaction
This elimination reaction gives a single product. Show its structure and explain why it is the only productformed.
How might the structure of DDT be modified to make it again effective against resistant insects?
Explain which product is formed when each of these alkyl chlorides reacts with sodium ethoxide in ethanol.
Explain which of these alkyl chlorides reacts faster with sodium ethoxide in ethanol.
Explain which product is formed when each of these alkyl chlorides reacts with sodium ethoxide in ethanol. Discuss.
Explain which elimination product is formed when this alkyl chloride is heated in ethanol.
Show the products of thesereactions:
Explain why only one of the two chlorines of 1, 2-dichloro-2-methylpropane is replaced by a hydroxy group when the compound is heated in water (see the preceding hydrolysis reaction.
On the basis of the bond cleavage shown for this reaction in Figure 10.1, predict the stereo chemistry of the product.Explain.
Show the products of thesereactions:
Show the products of thesereactions:
Diphenhydramine can also be synthesized by heating bromo diphenyl methane with the amino alcohol shown here. Offer a reason why the oxygen, rather than the nitrogen, of this compound acts as the
Explain which route would provide a better synthesis of theseethers:
Suggest a synthesis of these ethers starting with an alcohol and an alkylhalide:
Show the products of thesereactions:
Show all the steps in the mechanism for the reaction of 1-pentanol with sulfuric acid to form dipentyl ether.
Show the steps in the mechanism for the reaction of trans-2-chlorocyclohexanol with sodium hydroxide shown in the previous equation. Explain why cis-2-chlorocyclohexanol does not give a similar
Show the product, including stereo chemistry, for this reaction:
Because of the acidic conditions, this reaction proceeds by an SN1 mechanism. Which hydroxy group acts as the leaving group in the reaction? Show all the steps in the mechanism for this reaction:
Show the products of these reactions:
Show all the steps in the mechanism for the reactions of 2-methyl-2-butanol with HCl in water.
Suggest reagents that could be used to prepare these alkyl halides from alcohols:
Show the products of these reactions:
Show the products of thesereactions:
Suggest a method that could be used to prepare this amine from an alkyl halide: PhCH2CH2NH2
Show the products of thesereactions:
Show the products of thesereactions:
Suggest methods for preparing these compounds from alkylhalides:
Show the products of thesereactions:
Show the products of thesereactions:
Show the products of thesereactions:
Explain whether these elimination reaction would be a good way to prepare thesealkenes:
Explain which of these reactions would provide a better synthesis of2-pentene:
Show the products of thesereactions:
Show the products of thesereactions:
Show the products of thesereactions:
Show syntheses of these compounds from the indicated startingmaterials.
Show reactions that could be used to convert 1-butanol to thesecompounds:
Show reactions that could be used to convert the epoxide to these compounds. More than one step may benecessary.
Show how these compounds could be synthesized from alkylhalides:
Show how this synthesis might beaccomplished:
What is wrong with these reactions explain.
What is wrong with these synthesesexplain.

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