Carbon-Carbon Bond Formation Flashcards

This set of practice flashcards covers the mechanisms, reagents, and balanced equations for carbon-carbon bond formation as detailed in the lecture transcript, including nitriles, aromatic substitution, and Grignard reagents.

What is the primary importance of synthesis methods that form new $C-C$ bonds in the context of the pharmaceutical industry?

It underpins the industry by allowing for the synthesis of new organic molecules with longer carbon chains.

What reagents are used to form a nitrile ($-CN$) from a haloalkane?

Sodium cyanide ($NaCN$) or potassium cyanide ($KCN$) in ethanol.

What is the general equation for the reaction of a haloalkane ($R-X$) with sodium cyanide?

$$R-X + NaCN \rightarrow RCN + NaX$$

By what mechanism do haloalkanes react with cyanide ions to form nitriles?

Nucleophilic substitution.

What is the balanced equation for the reaction between 1-chlorobutane and potassium cyanide?

$$CH_3(CH_2)_3Cl + KCN \rightarrow CH_3(CH_2)_3CN + KCl$$

Which ion acts as a 'spectator ion' in the reaction between potassium cyanide and bromoethane?

The potassium ion ($K^+$).

What mechanism is involved in the formation of hydroxy nitriles from aldehydes and ketones using $HCN$?

Nucleophilic addition.

How can nitriles be reduced to form amines, and what catalyst is required?

By reacting with hydrogen ($H_2$) in the presence of a nickel ($Ni$) catalyst.

Write the balanced equation for the reduction of ethanenitrile to ethylamine.

$$CH_3CN + 2H_2 \xrightarrow{Ni} CH_3CH_2NH_2$$

What type of catalyst is the nickel used in the reduction of nitriles (where reactants and products are liquids)?

A heterogeneous catalyst (because $Ni$ is a solid).

What are the required conditions and reagents for the hydrolysis of nitriles to form carboxylic acids?

Heating in dilute aqueous acid, such as $HCl_{(aq)}$.

What is the balanced equation for the acid hydrolysis of propanenitrile ($CH_3CH_2CN$)?

$$CH_3CH_2CN + 2H_2O + HCl \rightarrow CH_3CH_2COOH + NH_4Cl$$

What is 'alkylation' in the context of aromatic compounds?

A way of attaching an alkyl group from a haloalkane directly to a benzene ring via an electrophilic substitution mechanism.

What catalyst is typically used in the Friedel–Crafts alkylation and acylation of benzene?

A halogen carrier, typically aluminium chloride ($AlCl_3$).

In the reaction of benzene with chloroethane, how is the $AlCl_3$ catalyst regenerated?

$$AlCl_4^{-} + H^{+} \rightarrow HCl + AlCl_3$$

How is 'acylation' of benzene performed, and what functional group is formed?

Benzene reacts with an acyl chloride in the presence of a halogen carrier to form a substituted aromatic ketone.

What is the name and nature of the nucleophile provided by Grignard Reagents like $CH_3MgBr$?

A carbanion, specifically $CH_3^{-}$, which undergoes nucleophilic addition.