
(a)
Interpretation: The given compounds must be arranged in increasing order of strength of their intermolecular forces.
Concept introduction: Intermolecular forces are those interactions among molecules by which the molecules either attract or repel each other. There are mainly four types of intermolecular interactions these are electrostatic, Van der Waals, dipole-dipole and hydrogen bonding. The electrostatic force is strongest and among the three types of intermolecular forces in covalent compounds van der Waals forces are weakest, dipole-dipole is intermediate and hydrogen bonding is the strongest.

Answer to Problem 3.28P
Increasing intermolecular forces
Explanation of Solution
The CH3CH3, ethane consists of only C – H and C – C bonds and these bonds are nonpolar thus the ethane has no permanent dipole moment therefore, ethane molecules are attracted to each other only by van der Waals forces.
The CH3Cl, chloromethane consists of C – H and C – Cl bonds among which C – Cl bond is polar since Cl is highly electronegative atom thus the chloromethane molecule possesses a permanent dipole moment. Therefore, chloromethane molecules are attracted to each other not only by van der Waals forces but also by dipole-dipole interactions.
The CH3NH2, methylamine consists of C – H, N – H and C – Cl bonds among which C – N and N – H bonds are polar since N is an electronegative atom thus the methylamine molecule possesses a permanent dipole moment. Therefore, methylamine molecules are attracted to each other not only by van der Waals forces but also by dipole-dipole interactions and since it contains a H-atom attached to an electronegative N-atom so CH3NH2 molecules will also be linked through Hydrogen bonding.
Increasing intermolecular forces
(b)
Interpretation: The given compounds must be arranged in increasing order of strength of their intermolecular forces.
Concept introduction: Intermolecular forces are those interactions among molecules by which the molecules either attract or repel each other. There are mainly four types of intermolecular interactions these are electrostatic, Van der Waals, dipole-dipole and hydrogen bonding. The electrostatic force is strongest and among the three types of intermolecular forces in covalent compounds van der Waals forces are weakest, dipole-dipole is intermediate and hydrogen bonding is the strongest.

Answer to Problem 3.28P
Increasing intermolecular forces
Explanation of Solution
The CH3Br molecule consists of only C – H and C – Br bonds among which C – Br bond is polar thus this molecule has permanent dipole moment therefore; these molecules are attracted towards each other not only by van der Waals forces but also by dipole-dipole interactions.
The CH3I molecule consists of only C – H and C – I bonds among which C – I bond is polar thus this molecule has permanent dipole moment therefore; these molecules are attracted towards each other not only by van der Waals forces but also by dipole-dipole interactions.
The CH3Cl molecule consists of only C – H and C – Cl bonds among which C – Cl bond is polar thus this molecule has permanent dipole moment therefore; these molecules are attracted towards each other not only by van der Waals forces but also by dipole-dipole interactions.
All these molecules are attracted to each other by van der Waals forces and dipole-dipole interactions. But with increase in size of the atom here halogen atoms the polarizability increases which results in the increase of intermolecular forces. Here, the size of halogen atoms increase with increase in
Increasing intermolecular forces
(c)
Interpretation: The given compounds must be arranged in increasing order of strength of their intermolecular forces.
Concept introduction: Intermolecular forces are those interactions among molecules by which the molecules either attract or repel each other. There are mainly four types of intermolecular interactions these are electrostatic, Van der Waals, dipole-dipole and hydrogen bonding. The electrostatic force is strongest and among the three types of intermolecular forces in covalent compounds van der Waals forces are weakest, dipole-dipole is intermediate and hydrogen bonding is the strongest.

Answer to Problem 3.28P
Increasing intermolecular forces
Explanation of Solution
The
The
The
Increasing intermolecular forces
(d)
Interpretation: The given compounds must be arranged in increasing order of strength of their intermolecular forces.
Concept introduction: Intermolecular forces are those interactions among molecules by which the molecules either attract or repel each other. There are mainly four types of intermolecular interactions these are electrostatic, Van der Waals, dipole-dipole and hydrogen bonding. The electrostatic force is strongest and among the three types of intermolecular forces in covalent compounds van der Waals forces are weakest, dipole-dipole is intermediate and hydrogen bonding is the strongest.

Answer to Problem 3.28P
Increasing intermolecular forces
Explanation of Solution
The CH3Cl molecule consists of only C – H and C – Cl bonds among which C – Cl bond is polar thus this molecule has permanent dipole moment therefore; these molecules are attracted towards each other not only by van der Waals forces but also by dipole-dipole interactions.
The CH3OH, methanol consists of C – H and O – H bonds among which O – H bond are polar since O is an electronegative atom thus the methanol molecule possesses a permanent dipole moment. Therefore, methanol molecules are attracted to each other not only by van der Waals forces but also by dipole-dipole interactions and since it contains a H-atom attached to an electronegative O-atom so CH3OH molecules will also be linked through Hydrogen bonding.
The NaCl molecule consists of only an ionic bond among Na+ and Cl- ions thus, these molecules are attracted towards each other by electrostatic interactions.
Increasing intermolecular forces
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Chapter 3 Solutions
Organic Chemistry
- A student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from the arrow. • Is the student's transformation possible? If not, check the box under the drawing area. . If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts, inorganic reagents, or other important reaction conditions above and below the arrow. • You do not need to balance the reaction, but be sure every important organic reactant or product is shown. + T X O O лет-ле HO OH HO OH This transformation can't be done in one step.arrow_forwardDetermine the structures of the missing organic molecules in the following reaction: X+H₂O H* H+ Y OH OH Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. X Sarrow_forwardPredict the major products of this organic reaction. If there aren't any products, because nothing will happen, check the box under the drawing area instead. No reaction. HO. O :☐ + G Na O.H Click and drag to start drawing a structure. XS xs H₂Oarrow_forward
- What are the angles a and b in the actual molecule of which this is a Lewis structure? H H C H- a -H b H Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal groups may have slightly different sizes. a = b = 0 °arrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? :0: HCOH a Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal that might be caused by the fact that different electron groups may have slightly different sizes. a = 0 b=0° Sarrow_forwardDetermine the structures of the missing organic molecules in the following reaction: + H₂O +H OH O OH +H OH X Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structure of the missing organic molecule X. Click and drag to start drawing a structure.arrow_forward
- Identify the missing organic reactant in the following reaction: x + x O OH H* + ☑- X H+ O O Х Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structure of the missing organic reactant X. Click and drag to start drawing a structure. Carrow_forwardCH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar Barrow_forwardWhat would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 2 2. n-BuLi 3 Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure.arrow_forward
- Predict the products of this organic reaction: NaBH3CN + NH2 ? H+ Click and drag to start drawing a structure. ×arrow_forwardPredict the organic products that form in the reaction below: + OH +H H+ ➤ ☑ X - Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Garrow_forwardPredict the organic products that form in the reaction below: OH H+ H+ + ☑ Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. ✓ marrow_forward
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