Organic Chemistry
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Propose a mechanism for the acid-catalyzed dehydration of alcohol shown below.
The following reaction shows the acid-catalyzed dehydration of an alcohol. Indicate how the equilibrium of this reaction could be shifted to the right.
The following reaction shows acid-catalyzed dehydration of an alcohol. Indicate how the equilibrium of this reaction can be shifted to the left.
Predict the structure of the alcohol that would yield the following alkene without rearrangement.
When HCl was used to perform the dehydration reaction of an alcohol, the desired product was not formed. Identify the product that was actually formed in this reaction.
Predict the major product formed in the following dehydration reaction.
Identify the alcohol that can be dehydrated to form the following alkene through carbocation rearrangement.
Identify the alcohol that can be dehydrated to form the following alkene without carbocation rearrangement.
Draw a mechanism for the reaction shown below.
Give the major products formed by dehydration of the given alcohols through sulfuric acid.
Show the products of the following acid-catalyzed dehydration reactions. Also, label them as major and minor.
When the following compound is heated in H2SO4, what constitutional isomer is formed as the major product? Indicate whether the product has any stereoisomers.
Predict the major product formed when the given compound is heated with H2SO4.
Draw the structure of the major product obtained when the given compound is heated with H2SO4.
Draw the major product in the reaction given below.
Provide two different reagents to carry out the following reaction.
When 3,3,5-trimethyl-2-hexanol and 2,3,5-trimethyl-2-hexanol are heated with H 2SO4, they both undergo dehydration to produce 2,3,5-trimethyl-2-hexene. Which of the two alcohols dehydrates faster?
Three alkenes are produced when the following seven-membered ring alcohol is dehydrated. Propose a mechanism to explain how they are formed.
Why do the following alcohols form two similar alkenes when heated with acid?
In the acid-catalyzed dehydration of 1-heptanol to 2-heptene, determine the stereoisomers formed and which of them would be the major product.
The dehydration of alcohols by acids is reversible, while the dehydrohalogenation of alkyl halides by bases is irreversible. Elucidate.
Provide the possible mechanism for the given reaction.
Provide a suitable mechanism for the reaction given below.
Show a suitable mechanism for the reaction given below.
Draw a suitable mechanism for the reaction given below.
Propose the major products expected from the sulfuric acid-catalyzed dehydration reactions of the following alcohols. Also. draw a mechanism to show the product formation.
Provide a suitable mechanism for the formation of major products in the following reaction.
Show the major products for acid-catalyzed dehydration of the following alcohols.
E1 elimination reactions of alkyl halides usually give a mixture of substitution and elimination products which is why these are not commonly used for synthetic purposes.On the other hand, the sulfuric acid-catalyzed dehydration of cyclopentanol gives a good yield of cyclopentene although it follows the same E1 mechanism. Explain why this reaction does not give substitution products.
Using 2-methyl-1-phenylpropan-1-ol and any other suitable reagents and solvents as starting material, show how (2-methylprop-1-en-1-yl)benzene can be synthesized.
Draw the structure of an alcohol that would yield the provided aromatic alkene under the specified conditions.
Draw the structure of an alcohol that would yield the desired alkene under the specified conditions.
In the absence of additional nucleophiles such as water or bromide ion, sulfuric acid can be utilized to isomerize less stable alkenes into their more stable counterparts. What is the mechanism for the acid-catalyzed isomerization of the following reaction?
What is the expected product of the pinacol rearrangement shown below?
Draw an arrow-pushing mechanism for the following elimination reaction.
Draw an arrow-pushing mechanism for the substitution reaction shown below.
Give the products that will result from the following reaction conditions. Write "no reaction" if no reaction occurs.
The following acid-catalyzed hydration of an alkene is reversible as shown below:
Is the forward or reverse reaction favored at high temperatures?
Draw the product for the following reaction of the given vicinal diol.
Draw the stereoisomers formed in the acid-catalyzed dehydration of 4,5-diethyloctan-4-ol to 4,5-diethyloct-4-ene. Which stereoisomer is the major product?
Choose the molecule in each pair that reacts via elimination at a faster rate when allowed to react with H2SO4 in the presence of heat.
Provide a brief explanation as to why a racemic mixture forms when (R)-5,5-dimethylhexan-2-ol is heated in H2SO4.
Draw the mechanism of the reaction given below.
Draw the products that form when pentan-1-ol undergoes an acid-catalyzed dehydration reaction.
Determine which molecule in the given pair of alcohols below would react faster when heated with H2SO4.
Which one from the given pair of alcohols would react faster when heated with H2SO4?
Determine which of the alcohols below would react faster when heated with H2SO4.
Propose a mechanism for the formation of each of the products in the following reaction. Note that alcohol dehydration reactions generally go by the E1 mechanism and rearrangements may occur.
Provide the mechanism for the reaction shown below. Note that alcohol dehydration reaction generally occurs via the E1 mechanism and carbocations formed may undergo rearrangements.
Illustrate the mechanism of the given dehydration reaction.
Draw the mechanism for the formation of the minor product through ring contraction when the given cycloheptanol undergoes dehydration.
Draw the mechanism of the following dehydration reaction.
When (5-methyltetrahydrofuran-2-yl)methanol undergoes an acid-catalyzed reaction, it gives good yields of 2-methyl-3,4-dihydro-2H-pyran. Draw the mechanism for this reaction.
Propose the mechanism of the given reaction.
Note: More products may be formed, but only show how the given products are formed in the reaction above.
Provide the balanced equation for the following:
Note: Only draw the major product.
Give the balanced equation for the following:
Draw the mechanism that explains the reaction below. Explain the failure to form the Zaitsev product.
Draw the expected product/s of the dehydration reaction of the following alcohol using heat and H2SO4. Show how the product/s is/are formed using an arrow-pushing mechanism.
Give the product/s of the dehydration reaction of the following alcohol using heat and H2SO4. Show how the product/s is/are formed using an arrow-pushing mechanism.
Draw the products of the acid-catalyzed dehydration of the compounds below. Identify the major and minor products if applicable.
i. 1-isopropylcyclopentanol
ii. 2-(sec-butyl)cyclopentanol
For the given reaction, draw its mechanism.
Note: More products may formed.
A pair of compounds is shown below. Explain why compound (a) reacts more quickly than compound (b) in an acid-catalyzed dehydration reaction.
Start with the given molecule and predict the product formed after undergoing a pinacol rearrangement.
Suggest a suitable mechanism for the following reaction
What alkene produces the given aldehyde via a two-step reaction mechanism involving a pinacol rearrangement?
The pinacol rearrangement begins with an acid-catalyzed ionization to give a carbocation. The carbocation then undergoes rearrangement to give a resonance-stabilized cation, which will give the product of the reaction after the loss of a proton. Draw a mechanism for the reaction shown below.
Consider the following reaction:
The expected product is A but the major product is B. What is the reaction mechanism by which B formed?
The dehydration of 2-(tert-butyl)-3,3-dimethylbutane-1,2-diol, in an acidic solution produces only one product. Determine the product.
A graduate student performing a complex organic synthesis required 1-ethylcyclopenta-1,3-diene as one of her compounds of interest. She started with 3-chloro-5-ethylcyclopent-1-ene and was able to convert it into 4-ethylcyclopent-2-en-1-ol. She then performed an acid-catalyzed dehydration on 4-ethylcyclopent-2-en-1-ol to convert it into her required compound. Write a mechanism for the dehydration reaction.
Determine the product of the following:
From the given alcohols, determine which would dehydrate the fastest when it undergoes an acid-catalyzed dehydration reaction.
Draw the mechanism of the given reaction below.
Note: Another product may be produced, but the most important thing is that the mechanism clearly shows how the desired product is formed.
Draw the major product when the given alcohols undergo an acid-catalyzed dehydration reaction.
(i) 2-ethylcyclopentan-1-ol
(ii) 2,2-dimethylbutan-1-ol
A vicinal diol is an alcohol with —OH groups on adjacent carbons. A rearrangement known as the pinacol rearrangement occurs when a vicinal diol dehydrates. Draw the plausible mechanism of the given reaction.
Note: More products may be formed. Only show how the given products are produced in the reaction.