Organic Chemistry
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Consider the following reactants,
What kind of elimination reaction is anticipated to take place with this condition?
Consider the given reactants,
What kind of elimination reaction is expected to happen with this condition?
Determine if the following reaction is E1 or E2 and draw its mechanism.
When stereochemistry is considered, what is the product of the following elimination reaction?
Consider the reactions below:
Which reaction, SN2 or E2, would occur at a higher temperature?
Which reaction condition favors elimination over substitution?
Which of the alkyl halides would undergo an SN1 or E1 reaction faster?
Does the following reaction undergo a E2, E1, SN2 or SN1 mechanism?
a. Draw the major products for each of the following reactions.
b. Determine whether each of these reactions follows an E2 or an E1 mechanism.
Draw the major products for the given reaction. Show stereochemistry where applicable.
Draw the major products expected from the elimination reaction of 4-bromo-2,4-dimethylpent-2-ene with methoxide ion.
Draw the major products expected from the elimination reaction shown below.
A small amount of a by-product is obtained during the Williamson ether synthesis of ethyl propyl ether using ethyl bromide. Draw the structure of this product.
A small amount of a by-product is obtained during the Williamson ether synthesis of ethyl propyl ether using propyl iodide. Draw the structure of this product.
Draw the three products formed in a reaction between 2-iodo-2-methylpropane and the aqueous solution of ethanol.
Draw the products formed in the reaction of 1-bromobutane with CH3S−.
Draw the products formed in the reaction of 1-bromobutane with HS−.
Draw the major elimination products of the following reaction, show their stereochemistry, and indicate the major and minor stereoisomers.
Draw the SN2 and E2 products expected from the following reaction. Show stereochemistry where applicable.
Draw the major products expected from the reaction shown below.
Draw the products for the below-given reaction and propose a suitable mechanism for their formation.
Draw the major products of the reaction given below.
Predict the major products of the reaction given below.
a. Draw the major products of the following reaction:
b. Are these products all optically active?
Predict the major elimination products of the below-given compound with a weak base and with a strong base.
Draw the product(s) obtained from the reaction given below.
Draw the product(s) obtained from the reaction shown below.
Draw the product(s) obtained in the following reaction of the stereoisomer of 2-bromo-1,3,5-trimethylcyclohexane.
When pure (3R,4R)-3-iodo-3,4-dimethylhexane is heated with sodium ethoxide in ethanol, it produces a mixture of three alkenes. Draw a mechanism that accounts for the formation of the three alkenes.
Determine the mechanism for the following reaction (E1, E2, SN1, or SN2).
In the case of multiple products, explain which one is the major product.
Write a balanced chemical equation that corresponds to the following reaction. Show the expected major product in the chemical equation you write.
Give the products of the reaction between a benzyl bromide derivative and sodium cyanide shown below.
Predict the major product for the following reaction:
When 1-chloro-2-methylcyclopentane is heated in methanol, the reaction yields two substitution and two elimination products. Predict the products and draw plausible mechanism for the formation of each product.
Alkyl halides when reacting with strong bases/nucleophiles often produce a mixture of substitution and elimination products. Draw expected products for the reaction between 1-iodo-2-methylcyclohexane and sodium methoxide. Note that Zaitsev's rule applies for E2 reactions when the base is not bulky.
For the following reaction, predict whether the major product will be a substitution product or an elimination product. Write the major product of the reaction.
Determine the elimination mechanism for the following reaction (E1 or E2, ignore substitution).
Predict major and minor elimination products of this reaction.
Determine the mechanism for the following reaction (E1 or E2).
Complete and balance the following reaction with the expected major product:
For the following reaction, write a mechanism that accounts for the formation of the shown products:
When pure (3R,4R)-3-iodo-3,4-dimethylhexane is heated in ethanol, it produces a mixture of two ethers and four alkenes. Draw a mechanism that accounts for the formation of the two ethers. Discuss the retention or inversion of configuration taking place in this reaction.
Select the correct chloroalkane and condition to produce the given alkene.
Identify the correct major product of the elimination reaction shown below. (Note: Pay attention to stereochemistry)
Give the correct major product of the elimination reaction given below. (Note: Pay attention to stereochemistry.)
Identify whether the given base favors an E2 or E1 mechanism.
The given reaction could undergo substitution or elimination:
What is its product? (Note: Pay attention to stereochemistry)
Predict the type of elimination reaction taking place with this condition.
Which reaction condition is more favorable to elimination over substitution?
Suggest a suitable base to produce the following alkenes from the initial alkyl halide.
Sketch the correct product of this reaction.
What is the product of the reaction given below?
From the two SN2 reactions given, which is faster? Justify.
From these two E2 reactions, which is faster? Justify.
What is the final product of the reaction below?
For the pair of reactions shown below, which one is expected to favor elimination over substitution?
Draw the product of the reaction shown below.
Consider the reaction below:
Determine whether the reaction favors an SN1, SN2, E1, or E2 mechanism.
Draw the major product(s) of the reaction when the molecule below is allowed to react with the following reagents: (i) H2O (ii) NaOH, H2O. If there is no reaction, write “no reaction.”
Determine via which mechanism the following reaction will occur: SN1, SN2, E1, or E2.
Identify whether the reaction below proceeds via E1, E2, SN1, or SN2.
Determine which reaction will favor elimination more than substitution.
Which of the given below will favor elimination reaction more than substitution reaction?
Three products are formed when the compound shown below undergoes solvolysis in ethanol. Propose a reaction mechanism for each of the products formed.
Predict which compound will form a cyclic ether at a higher rate.
What happens to the rate of the reaction of 1-bromopentane with ethoxide ion in DMSO if (i) the alkyl halide was changed to 1- iodopentane and if (ii) the alkyl halide was changed to 2-bromopentane? Explain.
Draw the major product formed in the following elimination reactions. If the major product formed can exist as stereoisomers, identify the stereoisomer that will be higher in amount and label it as the major product.
i. (R)-2-chloroheptane + high concentration of CH3CH2O–
ii. (R)-3-chloro-3-methyloctane + CH3CH2OH
Predict the products formed in the reactions shown below.
Determine the product for the given reactions. (Note: Show the correct configuration of each product.)
(i) 1-bromo-1-methylcyclopentane + CH3CH3O-
(ii) 1-bromo-1-methylcyclopentane + CH3CH2OH
Determine the resulting product if the molecule shown below undergoes two consecutive elimination reactions.
Draw the major product of the (i) SN2 and (ii) E2 reactions between (4S,5S)-4-bromo-2,5,7-trimethyloctane and CH3CH2O−. Note: Show the stereoisomers of the products formed.
Identify the products (including stereoisomers) of the reaction between 2-chloro-2-methylhexane and H2O.
Determine the products of the reactions shown below.
(i)
(ii)
Can the given reactions form both substitution and elimination products?
(i) 2-chloro-3-methylpentane + NaOH
(ii) 2-chloro-4-methylpentane+ NaOCH3
(iii) 3-chloro-2,3,4-trimethylpentane + NaOCH3
Can the reaction shown below undergo elimination, substitution, or both? What are its products? Identify the major product.
Reaction 1: 1-bromo-4-methylcyclohexane + NaOCH3 in CH3OH
Reaction 2: 1-bromo-4-methylcyclohexane + NaOC(CH3)3 in (CH3)3COH
Explain why one of the stereoisomers below undergoes heat-induced elimination with KOH more rapidly than the other. What are the products of the eliminations?
[Note that the hydrogens are drawn wedged and dashed as a guide.]
The silver-assisted solvolysis of (bromomethyl)cyclohexane in ethanol forms methylenecyclohexane. Show the mechanism for the formation of the product.
Give the mechanism for the following reaction to rationalize each of the products formed.
Draw the product of the following reaction.
meso-3,4-dichlorohexane + t-BuOK →
Note: Syn-coplanar E2 eliminations are rare, usually occurring when free rotation is not possible.
Identify if each reaction proceeds via SN2, E2, SN1, or E1, and draw the product/s. When more than one product or mechanism is possible, identify which is major and minor.
(i) 3-(iodomethyl)pentane + NaOH in water/ethanol
(ii) 3-(chloromethyl)pentane + AgNO3 in water/ethanol
The solvolysis of 3-(1-bromoethyl)-2,2,4,4-tetramethylpentane can produce several products, including both E1 and SN1 products, from the unrearranged and rearranged carbocation intermediate. Show all the possible products, including the carbocation intermediate from which they come, and indicate whether they are E1 or SN1 products.
The silver-assisted solvolysis of (bromomethyl)cyclohexane in ethanol forms several products. Propose a mechanism for the formation of the product shown below.
The silver-assisted solvolysis of (bromomethyl)cyclohexane in ethanol forms more than one product. Show the mechanism for how the product below was formed.
In the silver-assisted solvolysis of (bromomethyl)cyclohexane in ethanol, cycloheptene is one of the products formed. Propose a mechanism for the formation of cycloheptene.
A silver-assisted solvolysis of (bromomethyl)cyclohexane in ethanol forms ethoxycycloheptane and other products. Show a reaction mechanism for the formation of ethoxycycloheptane.
Given the following:
1-bromo-1-methylcyclopentane + triisopropylamine
Determine if it undergoes either substitution or elimination reaction, and predict the products. Which is the major product?
Give the products of the following substitution and elimination reactions.
2-bromo-2-methylbutane heated in methanol.
For the following reaction, predict the major and minor elimination products (for now, disregard any potential substitution reactions). Indicate if you anticipate it to be an E1 or E2 reaction.
Draw the plausible product(s) and the type of mechanism for the following reaction.
1−bromopentane + sodium methoxide in methanol
If there is more than one plausible product(s), indicate the major product, explain the type of reactions possible, and determine which is most likely.
Predict the plausible product(s) and the type of mechanism for the following reaction:
2−bromopentane + sodium ethoxide in ethanol
If there is more than one plausible product, indicate the major product, and explain the type of reactions possible: determine the most likely one. (Ignore stereochemistry.)
What product(s) would be formed in the reaction of the following compound with a moderately strong base? Remember: anti-coplanar E2 eliminations are common, while syn-coplanar E2 eliminations rarely occur.
What product would be formed in the reaction of the following compound with the strong base?
When (±)−2,3-dibromopentane reacts with sodium hydroxide, they form the following products.
Propose the mechanism that shows the formation of the products given.
Propose the mechanisms of reaction given below.
Note: More products may formed, but the mechanism needed is the one that shows how the products are formed.
Consider the pair of molecules below. Which molecule is more likely to favor SN1 and E1 reactions?
Determine the molecule that would have a faster reaction rate in an:
(i) E1 reaction
(ii) E2 reaction
Predict the products of the following SN2/E2 reaction. If stereoisomers can be formed, indicate which ones are produced.
(S)-2-chloro-3-ethylpentane + C2H5O−