Help with Substitution Reactions

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Organic Chemistry › Help with Substitution Reactions

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1

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II only

I only

I and II

III only

Explanation

Cyanide is a weak base and a good nucleophile, and the solvent is aprotic; therefore, the product is favored. This involves 100% inversion of stereochemistry; therefore II is favored.

2

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Classify the type of reaction given.

Substitution

Rearrangement

Addition

Elimination

Explanation

A substitution reaction is a chemical reaction that occurs when the reactants exchange atoms to form new products. In the reaction given the chloride in chloromethane is substituted for the hydroxide in sodium hydroxide to form methanol. Also the hydroxide in sodium hydroxide is substituted for the chloride in chloromethane to form sodium chloride.

3

Which of the following reaction conditions favors an SN1 mechanism?

Protic solvent

Weak base

Strong base

Strong nucleophile

Weak electrophile

Explanation

SN1 reactions occur in two steps. First, the leaving group leaves, forming a carbocation. Next, the weak nucleophile attacks the carbocation (beware of rearrangements during this step). The protic solvent stabilizes the carbocation intermediate.

4

Which of the following reaction conditions favors an SN2 mechanism?

Strong nucleophile

Protic solvent

Weak base

Strong base

Tertiary alkyl halide substrate

Explanation

SN2 reactions undergo substitution via a concerted mechanism. Thus, no carbocation is formed, and an aprotic solvent is favored. Furthermore, tertiary substituted substrates have lowest reactivity for SN2 reaction mechanisms due to steric hindrance.

5

Which of the following statements is true regarding an reaction?

An reaction is best carried out in a protic solvent, such as water or ethanol

The configuration at the site of the leaving group becomes inverted

The nucleophile that is substituted forms a pi bond with the electrophile

All of these

Explanation

An reaction is most efficiently carried out in a protic solvent. An inverted configuration site is characteristic of an reaction and the substituted nucleophile does not form a pi bond in an reaction.

6

Which of the following characteristics does not reflect an SN1 reaction mechanism?

Use of a strong nucleophile

Unimolecular reaction rate

Formation of a racemic mixture of products

Formation of a carbocation intermediate

Use of a protic solvent

Explanation

All of the given answers reflect SN1 reactions, except the claim that SN1 reactions are favored by weak nucleophiles.

SN1 reactions occur in two steps and involve a carbocation intermediate. The product demonstrates inverted stereochemistry (no racemic mixture). Tertiary substrates are preferred in this mechanism because they provide stabilization of the carbocation.

7

A solvolysis reaction occurs when dimethyl bromoethane is placed in methanol.

What is the final product?

2-methoxy-2-methylpropane

3-isoproxy-1-butanol

3-methoxy-2-ethylbutane

2-ethoxy-3-propanoic acid

Explanation

A solvolysis reaction is simply an reaction where the solvent acts as a nucleophile.

In this case, we start with a tertiary alkyl halide. Bromine, a stellar leaving group, leaves the substrate and leaves a carbocation intermediate. The methanol is then free to attack the carbon chain at the site of the carbocation to form an ether. The correct answer is 2-methoxy-2-methylpropane.

8

Which of the following characteristics does not reflect an SN2 reaction mechanism?

Tertiary substrate

Strong nucleophile

Aprotic solvent

Stereochemical inversion of the carbon attacked (backside attack)

Concerted mechanism

Explanation

SN2 reaction mechanisms are favored by methyl/primary substrates because of reduced steric hindrance. No carbocation is formed via an SN2 mechanism since the mechanism is concerted; thus a strong nuclephile is used.

9

In a substitution reaction __________.

one sigma bond is broken and one sigma bond is formed

one pi bond is broken and one pi bond is formed

one pi bond is broken and two sigma bonds are formed

two sigma bonds are broken and one pi bond is formed

one sigma and one pi bond are broken, and two sigma bonds are formed

Explanation

Substitution reactions—regardless of the mechanism—involve breaking one sigma bond, and forming another sigma bond (to another group).

10

What is the product of the reaction shown?

Image8

None of these

Explanation

The reaction shown is a nucleophilic substitution reaction. The molecule shown is a primary alkyl bromide, and the nucleophile that will be used is the iodide anion (). In this type of reaction the iodide will displace the bromide on the organic molecule, generating iodoethane ().

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