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List the type of organic reaction needed to perform each of the following transformations. a. alkene \(\rightarrow\) alkane b. alkyl halide \(\rightarrow\) alcohol c. alkyl halide \(\rightarrow\) alkene d. amine \(+\) carboxylic acid \(\rightarrow\) amide e. alcohol \(\rightarrow\) alkyl halide f. alkene \(\rightarrow\) alcohol

Short Answer

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a. Hydrogenation: \(\text{alkene} + H_2 \xrightarrow{\text{catalyst}} \text{alkane}\) b. Nucleophilic substitution: \(\text{alkyl halide} + \text{nucleophile} \rightarrow \text{alcohol} + \text{halide ion}\) c. Elimination: \(\text{alkyl halide} + \text{base} \rightarrow \text{alkene} + \text{hydrogen halide}\) d. Amide bond formation: \(\text{amine} + \text{carboxylic acid} \rightarrow \text{amide} + H_2O\) e. Substitution with a halogen reagent: \(\text{alcohol} + \text{halogen reagent} \rightarrow \text{alkyl halide} + \text{water or other byproduct}\) f. Oxymercuration-demercuration: \(\text{alkene} + Hg(OAc)_2 + H_2O \xrightarrow{\text{followed by NaBH_4}} \text{alcohol}\)

Step by step solution

01

Alkene to Alkane

To convert an alkene to an alkane, we need to perform a hydrogenation reaction. In this reaction, an alkene reacts with hydrogen in the presence of a metal catalyst to form an alkane. The general equation for hydrogenation is: \[ \text{alkene} + H_2 \xrightarrow{\text{catalyst}} \text{alkane} \]
02

Alkyl Halide to Alcohol

To convert an alkyl halide to an alcohol, we can use a nucleophilic substitution reaction. In this reaction, a nucleophile (e.g., hydroxide or water) replaces the halogen atom in the alkyl halide. The general equation for nucleophilic substitution is: \[ \text{alkyl halide} + \text{nucleophile} \rightarrow \text{alcohol} + \text{halide ion} \]
03

Alkyl Halide to Alkene

To convert an alkyl halide to an alkene, we can use an elimination reaction. In this reaction, a hydrogen atom and the halogen atom are removed from the alkyl halide, forming a double bond. The general equation for elimination is: \[ \text{alkyl halide} + \text{base} \rightarrow \text{alkene} + \text{hydrogen halide} \]
04

Amine + Carboxylic Acid to Amide

To convert an amine and a carboxylic acid to an amide, we can use a condensation reaction, specifically an amide bond formation. In this reaction, the amine reacts with the carboxylic acid, and a molecule of water is eliminated, resulting in the formation of an amide. The general equation for amide bond formation is: \[ \text{amine} + \text{carboxylic acid} \rightarrow \text{amide} + H_2O \]
05

Alcohol to Alkyl Halide

To convert an alcohol to an alkyl halide, we can use a substitution reaction with a halogen reagent. In this reaction, the hydroxyl group of the alcohol is replaced by a halogen atom. The general equation for this substitution is: \[ \text{alcohol} + \text{halogen reagent} \rightarrow \text{alkyl halide} + \text{water or other byproduct} \]
06

Alkene to Alcohol

To convert an alkene to an alcohol, we can use a hydroxylation reaction, specifically an oxymercuration-demercuration reaction. In this reaction, the alkene reacts with mercuric acetate and water, followed by reduction with sodium borohydride. The general equation for hydroxylation is: \[ \text{alkene} + Hg(OAc)_2 + H_2O \xrightarrow{\text{followed by NaBH_4}} \text{alcohol} \]

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Key Concepts

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

Hydrogenation Reaction
The hydrogenation reaction is a fundamental transformation in organic chemistry where alkenes are converted into alkanes by the addition of hydrogen atoms. This process typically occurs in the presence of a metal catalyst such as platinum, palladium, or nickel. Imagine the double bond of an alkene as an open door, and hydrogenation is like closing that door, making a more saturated molecule – the alkane.

During the hydrogenation, the catalyst provides a surface for the hydrogen molecules to split into atoms, which then attach to the carbon atoms of the alkene. This reaction is exothermic, releasing energy, and does not create any byproducts other than the desired alkane. The simplicity and efficiency of this reaction make it not only crucial in laboratory synthesis but also in industrial processes such as the production of margarine from vegetable oils.

Hydrogenation reactions can be tuned for selectivity in terms of which double bonds are hydrogenated, which is particularly useful in the processing of fats and oils containing multiple double bonds.
Nucleophilic Substitution Reaction
A nucleophilic substitution reaction involves the replacement of an atom or group of atoms (generally a leaving group like a halide) in a molecule with a nucleophile. This type of reaction is especially common when transforming alkyl halides into alcohols. The 'nucleophile' is a 'nucleus loving' species, which means it has electrons to share and is looking for a positive center to attack, like the one present in alkyl halides.

Nucleophilic substitution reactions can occur by two main mechanisms: SN1 and SN2. In an SN1 reaction, the leaving group departs before the nucleophile attaches, resulting in a carbocation intermediate. In an SN2 reaction, the removal of the leaving group and the addition of the nucleophile occur simultaneously in a single step, displaying a 'backside attack' mechanism.

These reactions are versatile and are not limited to the synthesis of alcohols; they can also be used to create a wide variety of other compounds by choosing different types of nucleophiles.
Elimination Reaction
An elimination reaction is a type of organic reaction where starting materials lose atoms or groups of atoms from adjacent carbons to form a double bond, resulting in the formation of alkenes from alkyl halides. This process typically involves the removal of a proton (a hydrogen atom) and a leaving group. Consider this as taking down two adjacent items from a shelf to join the shelf spaces.

Elimination reactions can follow two major mechanisms: E1 and E2. E1 involves a two-step mechanism with a carbocation intermediate, while E2 is a concerted one-step process where the proton and leaving group are removed simultaneously. The choice of base and conditions determines the pathway of the reaction and the degree of elimination. For example, a bulky base tends to give more substituted, stable alkenes through the Hofmann elimination product, while a less bulky base favors the Zaitsev rule, providing more substituted alkenes.

These reactions not only play a pivotal role in synthetic organic chemistry but also in biochemical processes such as the dehydration of alcohols to form alkenes.
Condensation Reaction
Condensation reactions are transformations in organic chemistry where two molecules combine to form one single molecule, accompanied by the loss of a small molecule like water, methanol, or hydrogen chloride. One classic example is the formation of amides from amines and carboxylic acids. Imagine two friends (the amine and the carboxylic acid) who decide to move in together (condense) and throw out an old couch (the water molecule).

The amide bond formation is a type of condensation reaction where the nitrogen of an amine group attacks the carbonyl carbon of a carboxylic acid. These reactions are essential for the formation of proteins in biochemistry, as amides link amino acids to form the peptide bonds in protein chains. In industrial applications, condensation reactions are used to create synthetic polymers, such as nylon and polyester.

A good understanding of condensation reactions is crucial for chemists, not only to synthesize new molecules but also to appreciate how biological systems operate at the molecular level.
Substitution Reaction
In a substitution reaction, one functional group in a chemical compound is replaced with another. When an alcohol is converted to an alkyl halide, this is a prime example of a substitution reaction at work. Think of this as swapping out one player in a sports team for a different player, where the overall structure of the team remains the same, but the new player brings different qualities.

Several types of substitution reactions exist, and in this context, we're often dealing with an SN1 or SN2 mechanism, similar to nucleophilic substitutions, but the nucleophile is now a halogen reagent. Factors such as the structure of the alcohol, the nature of the halogen reagent, and the reaction conditions will dictate the outcome and mechanism of the substitution reaction.

Being able to carry out substitution reactions efficiently is key to creating a broad array of compounds in both laboratory and industrial settings, providing chemists with a powerful tool for molecular modification.
Hydroxylation Reaction
A hydroxylation reaction is a chemical process involving the introduction of a hydroxyl group (-OH) into an organic compound, which in our case is the addition of a hydroxyl group to an alkene to form an alcohol. This transformation can be likened to adding a fresh splash of paint to a sculpture, where the alkene is the sculpture and the hydroxyl group the paint, enhancing the molecule's complexity and reactivity.

One way to hydroxylate alkenes is by the oxymercuration-demercuration process, which initially forms a carbon-mercury bond that is subsequently replaced by a hydroxyl group. This method is particularly advantageous as it avoids carbocation rearrangement, leading to regioselective addition of the hydroxyl group across the double bond.

Hydroxylation reactions are not only central to synthetic organic chemistry – where they enable the precise construction of complex molecules – but also to biology, where enzymes called hydroxylases play a crucial role in metabolizing substances in the body.

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