Organic Chemistry
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The dehydration of 2-(tert-butyl)-3,3-dimethylbutane-1,2-diol, a vicinal diol, in an acidic solution produces only one product.
Why is there only one product?
What is the primary product that results from an E1 reaction of the following compound?
Write a plausible mechanism for the following reaction:
Note that acid-catalyzed alcohol dehydrations usually go through the E1 mechanism. Rearrangements commonly take place.
For E1 and E2 reactions, which between 3-chlorocyclopent-1-ene and chlorocyclopentane would react faster?
What is the major product when the following alkyl halide undergoes an E1 reaction?
What is(are) the possible product(s) of the rearrangement-prone E1 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?
Give the products of E1 elimination of (Ph)3C−CH(CH3)Br. Identify the major products obtained in the reaction.
What is the product obtained from the following alkyl halide when it undergoes an E1 reaction?
Draw the structure of the major product expected to form in the following E1 reaction.
What products will be formed in the following E1 reaction?
The dehydration of 2-(tert-butyl)-3,3-dimethylbutane-1,2-diol, in an acidic solution produces only one product. Determine the product.
What is the reaction mechanism for the E1 reaction shown below?
Provide the possible major product for the elimination reaction shown below. (Note: Pay attention to stereochemistry.)
State the bonds that are formed and broken in the elimination reaction given below.
Draw the major product of the E1 reaction shown below.
Using electron-pushing arrows, illustrate the mechanism for the E1 reaction shown below.
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.
Draw a suitable mechanism for the E1 reaction shown below.
Determine the product of the following:
From the given alcohols, determine which would dehydrate the fastest when it undergoes an acid-catalyzed dehydration reaction.
Propose the possible mechanism for the elimination reaction shown below.
What is the corresponding E1 mechanism for the given reaction?
What is the product of the given E1 reaction that is prone to rearrangement?
What is the product of the following E1 reaction, which is susceptible to rearrangement?
Show the mechanism for the following E1 reaction.
What is the major product for the elimination reaction given below? When necessary, show the resulting stereochemistry.
Consider the pair of molecules below. Which molecule is more likely to favor SN1 and E1 reactions?
For the following elimination reaction, give the mechanism.
Draw the mechanism for the given E1 reaction.
What is the electron-pushing mechanism for the elimination reaction given below?
Determine how the (i) strength and (ii) concentration of the base affects E1 reactions. How about the (iii) solvent?
Draw the product for the E2 reaction of (1S,2S)-1-bromo-1,2-diphenylpentane and CH3ONa. Indicate the configuration.
Determine the compound that produces a faster E1 reaction.
Provide the major products of the reaction of the alkyl halides below via the E1 mechanism.