Chapter 22: Problem 49
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
Step by step solution
Alkene to Alkane
Alkyl Halide to Alcohol
Alkyl Halide to Alkene
Amine + Carboxylic Acid to Amide
Alcohol to Alkyl Halide
Alkene to Alcohol
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Hydrogenation Reaction
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
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
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
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
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
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.