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Which of these form intermolecular hydrogen bonds? (a) \(\mathrm{CH}_{2} \mathrm{Br}_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{COOH}\) (d) \(\mathrm{H}_{2} \mathrm{SO}_{3}\) (e) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)

Short Answer

Expert verified
(c) \( \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{COOH} \), (d) \( \mathrm{H}_{2} \mathrm{SO}_{3} \), and (e) \( \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \) form hydrogen bonds.

Step by step solution

01

Understand Hydrogen Bonding

To determine whether a compound can form intermolecular hydrogen bonds, we need to check for hydrogen atoms attached to highly electronegative atoms like nitrogen, oxygen, or fluorine. These electronegative atoms must also have lone pairs for hydrogen bonding.
02

Analyze Compound (a) \\( \mathrm{CH}_{2} \mathrm{Br}_{2} \\)

In dibromomethane (\( \mathrm{CH}_{2} \mathrm{Br}_{2} \)), there are no hydrogen atoms attached to highly electronegative atoms such as nitrogen, oxygen, or fluorine. Thus, it cannot form hydrogen bonds.
03

Analyze Compound (b) \\( \mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{3} \\)

In dimethyl ether (\( \mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{3} \)), the oxygen atom is electronegative, but the hydrogens are attached to carbon, not oxygen. Therefore, it cannot form hydrogen bonds.
04

Analyze Compound (c) \\( \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{COOH} \\)

In glycine (\( \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{COOH} \)), there is a hydrogen atom attached to nitrogen in the amine group and another to oxygen in the carboxylic acid group. Both nitrogen and oxygen have lone pairs, allowing for hydrogen bonding.
05

Analyze Compound (d) \\( \mathrm{H}_{2} \mathrm{SO}_{3} \\)

In sulfurous acid (\( \mathrm{H}_{2} \mathrm{SO}_{3} \)), the hydrogen atoms are attached to oxygen atoms. Given that oxygen is electronegative and has lone pairs, this compound can form hydrogen bonds.
06

Analyze Compound (e) \\( \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \\)

In ethanol (\( \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \)), the hydrogen atom is attached to oxygen, which is electronegative. This setup enables it to form hydrogen bonds.

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Key Concepts

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

Intermolecular Forces
Intermolecular forces are the forces of attraction or repulsion between neighboring particles such as atoms, molecules, or ions. These forces, although weaker than covalent and ionic bonds, play an essential role in determining the physical properties of substances like boiling points, melting points, and solubility. There are various types of intermolecular forces:
  • **London Dispersion Forces** (also called induced dipole-induced dipole): These are the weakest forces and occur due to temporary shifts in electron density.
  • **Dipole-Dipole Interactions**: These occur when polar molecules align such that positive ends of one molecule are attracted to negative ends of another.
  • **Hydrogen Bonds**: A special type of dipole-dipole attraction, where hydrogen is covalently bonded to F, O, or N, and is attracted to F, O, or N in another molecule.

Intermolecular forces are crucial in understanding the behavior of molecules in different states of matter.
Electronegativity
Electronegativity is a measure of an atom's ability to attract and hold onto electrons within a chemical bond. Different elements have varying electronegativities based on their position in the periodic table. Atom's electronegativity plays a significant role in forming polar covalent bonds, where electrons are unequally distributed between atoms, leading to dipole formation.

For example, in a water molecule (H2O), oxygen is more electronegative than hydrogen, thus attracting the shared electrons more strongly and creating a partial negative charge on the oxygen and a partial positive charge on the hydrogen atoms. This disparity is critical for hydrogen bonding.
  • Electronegative elements like nitrogen, oxygen, and fluorine are crucial for hydrogen bonding since they attract shared electrons, creating the needed polarity.
Recognizing the differences in electronegativity helps determine the possibility of hydrogen bond formation between molecules.
Hydrogen Bonds
Hydrogen bonds are a special type of strong dipole-dipole interaction formed when hydrogen is directly bonded to highly electronegative elements like nitrogen (N), oxygen (O), or fluorine (F), each having lone pairs of electrons. This creates a region with a partial positive charge (hydrogen) and a partial negative charge (N, O or F).

This scenario allows for the attraction between the positively charged hydrogen and the lone pair electrons of another electronegative atom in a nearby molecule, forming a hydrogen bond. Hydrogen bonds are crucial for the properties of water, proteins, and nucleic acids.
  • For example, ethanol (CH3CH2OH) can form hydrogen bonds due to the OH group, where hydrogen is attracted to the lone pairs on an oxygen of another molecule.
  • Another example is glycine ( olinebreak H2NCH2COOH), which can form hydrogen bonds due to the presence of amino and carboxylic groups.
Understanding hydrogen bonds helps explain the high boiling points and unique properties of compounds like water and ethanol.

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Most popular questions from this chapter

Explain why water "beads up" on a freshly waxed car, but not on a dirty, unwaxed car.

Which of these molecules is (are) polar? For each polar molecule, what is the direction of polarity; that is, which is the partial negative end and which is the partial positive end of the molecule? (a) \(\mathrm{CO}_{2}\) (b) \(\mathrm{HBF}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{Cl}\) (d) \(\mathrm{SO}_{3}\)

Draw the Lewis structure and identify the molecular shape of each molecule. (a) \(\mathrm{BeH}_{2}\) (b) \(\mathrm{CH}_{2} \mathrm{Cl}_{2}\) (c) \(\mathrm{BH}_{3}\) (d) \(\mathrm{SeCl}_{6}\) (e) \(\mathrm{PF}_{3}\)

The grid for Question 79 has nine lettered boxes, each of which contains an item that is used to answer the questions that follow. Items may be used more than once and there may be more than one correct item in response to a question. $$ \begin{aligned} &\text { Grid for Question } 79\\\ &\begin{array}{|l|l|l|} \hline \text { A } & \text { B } & \text { C } \\ \text { HCN } & \text { PO }_{4}^{3-} & \text { PH }_{3} \text { or } \mathrm{PF}_{3} \\ \hline \text { D } & \text { E } & \text { F } \\ \text { SiH }_{4} & \text { Cl }_{2} \mathrm{O} & \text { NH }_{2} \text { Cl } \\ \hline \text { G } & \text { H } & \text { I } \\ \text { HF or } \mathrm{F}_{2} & \text { CH }_{4} & \text { OF }_{2} \\ \hline \end{array} \end{aligned} $$ Place the letter(s) of the correct selection(s) on the appropriate line. (a) Electron-region geometry is the same as the molecular geometry_____ (b) Nonpolar molecule____ (c) Linear molecular geometry______ (d) Angular (bent) molecular geometry______ (e) Central atom is \(s p^{3}\) hybridized______ (f) Central atom is sp hybridized_____ (g) Which one in each pair of compounds has the lower boiling point?_____ (h) Which one in each pair of compounds has the higher vapor pressure?______ (i) Which one in each pair of compounds has the higher dipole moment?______ (j) Has dipole-dipole and hydrogen bonding intermolecular forces______

(a) Identify the type of hybridization and approximate bond angle for each carbon atom in \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CCH}\). (b) Which is the shortest carbon-to-carbon bond length in this molecule? (c) Which is the strongest carbon-to-carbon bond in this molecule?

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