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The following substances have boiling points as indicated: ethyl ethanoate \(\left(77^{\circ}\right)\) ethanoic anhydride \(\left(140^{\circ}\right)\) ethanoic acid \(\left(118^{\circ}\right)\) ethanamide \(\left(221^{\circ}\right)\) Account for these differences on the basis of molecular weight and hydrogen bonding.

Short Answer

Expert verified
Boiling points vary due to molecular weights and hydrogen bonding, with strong hydrogen bonding leading to higher boiling points.

Step by step solution

01

Identify Molecular Weights

First, calculate the molecular weights of each compound. Ethyl ethanoate (C₄H₈O₂) has a molecular weight of 88 g/mol, ethanoic anhydride (C₄H₆O₃) has a molecular weight of 102 g/mol, ethanoic acid (C₂H₄O₂) has a molecular weight of 60 g/mol, and ethanamide (C₂H₅NO) has a molecular weight of 59 g/mol.
02

Analyze Hydrogen Bonding Capacity

Next, identify hydrogen bonding capabilities. Ethanoic acid and ethanamide both have strong hydrogen bonding due to the presence of -OH and -NHâ‚‚ groups, respectively. Ethyl ethanoate and ethanoic anhydride have little or no hydrogen bonding, lacking these groups.
03

Link Boiling Points to Molecular Interactions

Now, connect boiling points to molecular interactions. Higher boiling points result from stronger intermolecular forces. Ethanamide has the highest boiling point due to strong hydrogen bonding. Ethanoic acid also has significant hydrogen bonding, giving it a high boiling point, but not as high as ethanamide. Ethanoic anhydride has a relatively high boiling point due to its higher molecular weight and some dipole interactions. Ethyl ethanoate has the lowest boiling point, attributed to its lower molecular weight and minimal hydrogen bonding.

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Key Concepts

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

Molecular Weight
Molecular weight, often referred to as molar mass, is the sum of the atomic weights of all atoms in a molecule. It plays a crucial role in determining various physical properties of a substance. In the context of boiling points, molecular weight can influence the energy required to transition a substance from liquid to gas.
Generally, compounds with higher molecular weights will have higher boiling points. This is because more energy is required to overcome the greater number of interactions between the larger number of atoms. For example, ethanoic anhydride \(C_4H_6O_3\), with a molecular weight of 102 g/mol, has a relatively high boiling point of 140°C. This is due in part to its larger molecular structure compared to ethanoic acid \(C_2H_4O_2\) with 60 g/mol. However, molecular weight isn't the sole factor; intermolecular forces also play a significant role.
Boiling Points
Boiling points are a measure of the temperature at which a substance transitions from liquid to gaseous state. This phase change is strongly influenced by the nature of the forces acting between the molecules, known as intermolecular forces.
For instance, ethanamide \(C_2H_5NO\) exhibits a very high boiling point of 221°C because it can form strong hydrogen bonds due to the presence of \(-NH_2\) groups. Hydrogen bonds are much stronger than other types of dipole-dipole interactions. The boiling point of a compound is thus not only a factor of molecular weight but also the strength and nature of its intermolecular forces.
Therefore, assessing both molecular weight and intermolecular interactions can give a comprehensive view of why certain substances boil at higher temperatures.
Intermolecular Forces
Intermolecular forces are the forces that mediate interaction between molecules, including forces of attraction or repulsion which act between molecules and other types of neighboring particles. These forces determine a wide range of physical properties, including boiling points.
One of the strongest types of intermolecular forces is hydrogen bonding. This specific interaction occurs when a hydrogen atom, covalently bonded to a highly electronegative atom like oxygen or nitrogen, attracts another electronegative atom. For example, ethanoic acid \(C_2H_4O_2\) can form hydrogen bonds because it contains hydroxyl \(-OH\) groups, which increases its boiling point to 118°C.
In contrast, ethyl ethanoate \(C_4H_8O_2\) lacks these groups and thus experiences weaker Van der Waals forces only, resulting in a lower boiling point of 77°C. Therefore, the strength of intermolecular forces like hydrogen bonding is key to understanding the differences in boiling points among substances.

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Most popular questions from this chapter

Benzoic acid is not esterified by the procedure that is useful for \(2,4,6\) -trimethylbenzoic acid because, when benzoic acid is dissolved in sulfuric acid, it gives the conjugate acid and no acyl cation. Explain why the acyl cation, 11 of \(2,4,6\) -trimethylbenzoic acid might be more stable, relative to the conjugate acid of benzoic acid.

Grignard reagents add to \(\mathrm{N}, \mathrm{N}\) -dialkylalkanamides, \(\mathrm{RCONR}_{2}^{\prime}\), to give ketones after hydrolysis. With esters or acyl chlorides, a tertiary alcohol is the usual product. Explain why, on the basis of the stability of the \(\mathrm{RR}^{\prime} \mathrm{CZ}(\mathrm{OMgX})\) intermediate, the amides may be expected to be less likely than esters or acyl chlorides to give tertiary alcohols. How could you use an N,N-dialkylalkanamide to prepare an aldehyde with the aid of a Grignard reagent?

Write structures for all of the Claisen condensation products that reasonably may be expected to be formed from the following ester mixtures and sodium ethoxide: a. ethyl ethanoate and ethyl propanoate b. diethyl carbonate and 2 -propanone c. diethyl ethanedioate and ethyl 2,2-dimethylpropanoate

Explain why the Michael addition of diethyl propanedioate to 3-phenylpropenoic acid is unlikely to be successful.

Write equations for a practical laboratory synthesis of each of the following substances from the indicated starting materials (several steps may be required). Give reagents and conditions. a. 2 -chloroethyl bromoethanoate from ethanol and/or ethanoic acid b. 2 -methoxy-2-methylpropanamide from 2 -methylpropanoic acid c. 3,5,5-trimethyl-3-hexanol from 2,4,4-trimethyl-1-pentene (commercially available) d. 3,3-dimethylbutanal from 2,2-dimethylpropanoic acid e. \(2,3,3\) -trimethyl-2-butanol from 2,3-dimethyl-2-butene

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