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Chapter 11: Problem 7

Which of the following is strongest nucleophile? (a) \(\mathrm{Br}^{-}\) (b) : \(\mathrm{OH}^{-}\) (c) : \(\overline{\mathrm{CN}}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{5} \overline{\mathrm{O}}:\)

Short Answer

Expert verified
The strongest nucleophile is (d) C鈧侶鈧匫鈦�.

Step by step solution

01

Understand Nucleophilicity

Nucleophilicity refers to the ability of a molecule or ion to donate a pair of electrons to an electron-deficient atom. In general, a stronger base is also a stronger nucleophile.
02

Analyze the List of Nucleophiles

We are given four nucleophiles: (a) Br鈦� (b) OH鈦� (c) CN鈦� (d) C鈧侶鈧匫鈦�. We need to determine the strongest nucleophile among them.
03

Consider Basicity and Solvent Effects

Typically in a polar protic solvent, the basicity order relates to their nucleophilicity in the following manner: alkoxide (RO鈦�) > cyanide (CN鈦�) > hydroxide (OH鈦�) > halide (Br鈦�). This is because alkoxide and cyanide ions are stronger bases and are less hindered.
04

Compare Nucleophilicity

Considering their basicity, C鈧侶鈧匫鈦� is the strongest base among the four, followed by CN鈦�, OH鈦�, and finally Br鈦�. Therefore, the nucleophilicity order generally follows this trend as well in a protic solvent.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Basicity
The concept of basicity revolves around the ease with which a molecule or ion donates an electron pair. Basicity is akin to nucleophilicity, but there are distinctions depending on the reaction environment. In simple terms, a base accepts protons, which is a slightly different measure than how nucleophiles donate electron pairs. Basicity often influences nucleophilicity because a stronger base generally acts as a better nucleophile.
  • Stronger bases have higher tendencies to donate their electrons, making them active participants in chemical reactions.
  • Basicity is often evaluated in terms of the equilibrium constant for the base's reaction with protons (H鈦�).
It's essential to understand that the listed substances, C鈧侶鈧匫鈦� and CN鈦�, showcase different levels of basicity and nucleophilicity.
These differences can vary based on the solvent and specific reaction conditions.
Protic Solvent
A protic solvent is a type of solvent that has a hydrogen atom bonded to an electronegative element, usually oxygen or nitrogen. This allows the solvent to donate protons, thus impacting the reactivity of bases and nucleophiles in solution.
  • Protic solvents, like water or alcohols, can participate in hydrogen bonding.
  • This characteristic can sometimes diminish the nucleophilicity of certain ions.
When analyzing nucleophiles in a protic solvent, we often see that larger, less basic ions become relatively better nucleophiles.
This is because they are less hindered by hydrogen bonding, allowing them to remain more active in reactions. In our context, this is why C鈧侶鈧匫鈦� remains a strong nucleophile despite the solvent environment.
Alkoxide Ion
An alkoxide ion is an anion commonly denoted as RO鈦�. These ions are derived when an alcohol loses its proton, leading to the negative charge on the oxygen. Alkoxide ions are noteworthy due to their substantial basicity and nucleophilicity.
  • The C鈧侶鈧匫鈦� ion, specifically ethoxide, is an example of an alkoxide ion that is both a potent base and nucleophile.
  • These ions excel in reactions where they can directly donate their electron pair to form new bonds.
In our scenario, C鈧侶鈧匫鈦� stands as the strongest nucleophile among the given options. This is primarily due to its high basicity and ability to donate electrons efficiently,
making it suitable for many chemical processes.
Cyanide Ion
The cyanide ion, depicted as CN鈦�, represents a composite ion of carbon and nitrogen with a negative charge. Cyanide ions are renowned for their robust nucleophilicity owing to the presence of electronegative nitrogen and its ability to stabilize the electron pair.
  • CN鈦� ions effectively participate in addition reactions with carbonyl groups.
  • Their low steric hindrance enables them to act efficiently as nucleophiles in many organic reactions.
In a protic solvent, the cyanide ion may see some reduction in its effectiveness compared with aprotic environments. Nonetheless, CN鈦� remains formidable due to its nucleophilic identification and essential role in various syntheses.

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Most popular questions from this chapter

Which of the following is optically active? (a) Butane (b) 2 -methylpentane (c) 4-methylpent ane (d) 3 -methylheptane

Which of the following has zero dipole moment? (a) 1-butene (b) Cis-2-butene (c) Trans-2-butene (d) 2 methyl-1-propene

Which of the following represents the given mode of hybridization \(\mathrm{sp}^{2}-\mathrm{sp}^{2}-\mathrm{sp}-\mathrm{sp}\) from left to right? (a) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{C} \equiv \mathrm{NCH}\) (b) \(\mathrm{CH} \equiv \mathrm{C}-\mathrm{C} \equiv \mathrm{N}\) (c) \(\mathrm{CH}_{2}=\mathrm{C}=\mathrm{C}=\mathrm{CH}_{2}\) (d) \(\mathrm{CH}_{2}\)

Phenol is more reactive than benzene towards eletrophillic substitution due to: (a) Strong mesomeric effect (b) Hyperconjugative effect (c) Inductive effect only (d) Hydrogen bonding

An organic molecule necessarily shows optical activity if it (a) Is non-superimposable on its mirror image (b) Is superimposable on its mirror image (c) Contains asymmetric carbon atoms (d) Is non-polar
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