Question

Draw as many compounds as you can that fit the following descriptions: (a) Alcohols with formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) (b) Amines with formula \(\mathrm{C}_{5} \mathrm{H}_{13} \mathrm{~N}\) (c) Ketones with formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\) (d) Aldehydes with formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\) (e) Esters with formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{2}\) (f) Ethers with formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\)

Short answer

There are numerous structural possibilities for each type of compound given the molecular formulas.

Step-by-step solution

Understand the Problem

We need to draw various compounds that fit specific molecular formulas and functional groups. Each part specifies a certain type of compound (e.g., alcohol, amine) with a given molecular formula. Our task is to determine possible structures that conform to these criteria.

Analyze Part (a) - Finding Alcohol Structures

For alcohols with formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\), the general structure is \(\mathrm{R-OH}\), where \(\mathrm{R}\) is an alkyl group. Possible structures include:1. Butan-1-ol: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}\mathrm{OH}\)2. Butan-2-ol: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}(-\mathrm{OH})-\mathrm{CH}_{3}\)3. 2-Methylpropan-1-ol: \(\mathrm{CH}_{3}-\mathrm{CH}(-\mathrm{CH}_{3})-\mathrm{CH}_{2}\mathrm{OH}\)4. 2-Methylpropan-2-ol: \(\mathrm{(CH}_{3})_{3}\mathrm{C-OH}\)

Analyze Part (b) - Finding Amine Structures

For amines with formula \(\mathrm{C}_{5} \mathrm{H}_{13} \mathrm{N}\), amines can be primary, secondary, or tertiary. Possible structures include:1. Pentan-1-amine: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}\mathrm{NH}_{2}\)2. Pentan-2-amine: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}(-\mathrm{NH}_{2})-\mathrm{CH}_{3}\)3. 2-Methylbutan-2-amine: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{C}(-\mathrm{NH}_{2})(-\mathrm{CH}_{3})\)

Analyze Part (c) - Finding Ketone Structures

For ketones with formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\), the structure is \(\mathrm{R}-\mathrm{C}(=\mathrm{O})-\mathrm{R'}\). Possible structures include:1. Pentan-2-one: \(\mathrm{CH}_{3}-\mathrm{C}(=\mathrm{O})-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)2. Pentan-3-one: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{C}(=\mathrm{O})-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)3. 3-Methylbutan-2-one: \(\mathrm{CH}_{3}-\mathrm{C}(=\mathrm{O})(-\mathrm{CH}_{3})-\mathrm{CH}_{2}\mathrm{CH}_{3}\)

Analyze Part (d) - Finding Aldehyde Structures

For aldehydes with formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\), the structure is \(\mathrm{R}-\mathrm{CH}=\mathrm{O}\). Possible aldehydes include:1. Pentanal: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CHO}\)2. 3-Methylbutanal: \(\mathrm{(CH}_{3})_{2}-\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{CHO}\)

Analyze Part (e) - Finding Ester Structures

For esters with formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{2}\), the structure is generally \(\mathrm{R}-\mathrm{C}(=\mathrm{O})-\mathrm{O}-\mathrm{R'}\). Possible structures include:1. Methyl propanoate: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{C}(=\mathrm{O})-\mathrm{O}-\mathrm{CH}_{3}\)2. Ethyl ethanoate: \(\mathrm{CH}_{3}-\mathrm{C}(=\mathrm{O})-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)

Analyze Part (f) - Finding Ether Structures

For ethers with formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\), the general structure is \(\mathrm{R}-\mathrm{O}-\mathrm{R'}\). Possible ethers include:1. Diethyl ether: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)2. Methyl propyl ether: \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)

Key concepts

Alcohols

Alcohols are a common functional group in organic chemistry, characterized by an -OH group attached to a carbon atom. The molecular formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) represents several possible alcohol structures, including butan-1-ol and butan-2-ol. Each of these structures has a hydroxyl group (-OH) which impacts their chemical and physical properties. For instance, this hydroxyl group allows for hydrogen bonding, which increases the boiling point of alcohols compared to alkanes of similar molecular weight. Additionally, the solubility in water varies with the length of the carbon chain; shorter chains are more soluble due to the hydrophilic nature of the -OH group.

Amines

Amines are organic compounds derived from ammonia and possess a nitrogen atom attached to one or more alkyl groups. For amines with the formula \(\mathrm{C}_{5} \mathrm{H}_{13} \mathrm{~N}\), their diversity increases with the type of amine structure: primary (one alkyl group attached), secondary (two alkyl groups), or tertiary (three alkyl groups). Pentan-1-amine is an example of a primary amine, while 2-methylbutan-2-amine can be considered a secondary amine. Amines also exhibit distinct properties such as being basic, reacting with acids to form ammonium salts, and their characteristic fishy odor due to volatile amines. These properties make them essential in various chemical processes and industrial applications.

Ketones

Ketones feature a carbonyl group (C=O) flanked by two carbon atoms, making them distinct from aldehydes. The structure \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\) represents ketones like pentan-2-one. Ketones are generally more polar than alkanes and hence have higher boiling points and solubility in water. Their unique property of having two carbon groups allows them to act as solvents in chemical reactions; one well-known example is acetone. Additionally, ketones do not easily form hydrogen bonds, which influences how they interact within chemical mixtures and solutions.

Aldehydes

Aldehydes are recognized by the presence of a formyl group (R-CHO), where the carbon is double-bonded to oxygen. Their molecular formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\) includes structures such as pentanal. Aldehydes tend to be more reactive than ketones because of the hydrogen atom attached to the carbonyl carbon, which makes them key components in various chemical synthesis processes. They can undergo oxidation to form carboxylic acids and are often used in perfumery and flavoring due to their distinct aromas.

Esters

Esters have a distinct functional group where an oxygen is bonded to the carbon of a carbonyl group (\(-C(=O)O-\)). The molecular formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{2}\) describes esters like methyl propanoate. Esters are widely known for their pleasant scents and are commonly used in fragrances and flavorings. The lack of a hydrogen atom bonded to the oxygen prevents esters from hydrogen bonding as alcohols do, affecting their physical and chemical properties. Their relatively low boiling points, compared to carboxylic acids, make them ideal solvents in many reactions.

Ethers

Ethers consist of an oxygen atom connected to two alkyl or aryl groups, following the formula \(\mathrm{R}-\mathrm{O}-\mathrm{R'}\). In \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\), ethers such as diethyl ether are represented. Ethers, due to their structure, are generally non-polar and have lower boiling points compared to alcohols with similar molecular weights. This non-polar characteristic makes them excellent solvents, as they do not easily coordinate with metal ions or form hydrogen bonds with solutes. However, their inertness to most reagents makes them less reactive, a distinct advantage when stability in reactions is desired.