e. melts rather than sublimes under ordinary conditions, Crystalline solids differ from amorphous solids in that crystalline solids have_____ Ans: 33 sigma bonds and 4 pi bonds (19 sigma, 4 pi) Category:Medium Section:10.5 29. Identify the compounds with a hydrogen atom attached to O, N, or F. These are likely to be able to act as hydrogen bond donors. A.Hydrogen bonds involve hydrogen bonded to carbon, nitrogen, oxygen, or fluorine. Because the boiling points of nonpolar substances increase rapidly with molecular mass, C60 should boil at a higher temperature than the other nonionic substances. In contrast, the hydrides of the lightest members of groups 1517 have boiling points that are more than 100C greater than predicted on the basis of their molar masses. Indicate all the types of intermolecular forces of attraction in CF4(g). e. Large molecules, regardless of their polarity. Which of the responses includes all of the following that can form hydrogen bonds with water molecules? The key is to know which bonds require more energy for boiling to occur. a) ion-ion attractions For example, part (b) in Figure \(\PageIndex{4}\) shows 2,2-dimethylpropane (neopentane) and n-pentane, both of which have the empirical formula C5H12. A) XeF4 B) BF3 C) AsF5 D) CF4 E) NH3 Ans:D Category:Medium Section:10.1 16. A larger molecule is more polarizable, which is an attraction that keeps the molecules together. A) 35.1 kJ/mol B) 13.5 kJ/mol C) +13.5 kJ/mol D) 35.1 kJ/mol E) Not enough information is given to answer the question. The one compound that can act as a hydrogen bond donor, methanol (CH3OH), contains both a hydrogen atom attached to O (making it a hydrogen bond donor) and two lone pairs of electrons on O (making it a hydrogen bond acceptor); methanol can thus form hydrogen bonds by acting as either a hydrogen bond donor or a hydrogen bond acceptor. 5 2 1 . Ans: dispersion Category:Medium Section:11.2 33. Molecules in liquids are held to other molecules by intermolecular interactions, which are weaker than the intramolecular interactions that hold the atoms together within molecules and polyatomic ions. The polarizability of a substance also determines how it interacts with ions and species that possess permanent dipoles. For example, Xe boils at 108.1C, whereas He boils at 269C. What is the expected value for the heat of sublimation of acetic acid? Give the number of lone pairs around the central atom and the molecular geometry of XeF4. A) Na B) As C) Ga D) Cs E) Sb Ans:B Category:Medium Section:9.5 16. Consequently, N2O should have a higher boiling point. Which of the following is not a type of solid? A) O B) S C) Na D) C E) N Ans:B Category:Easy Section:9.9 34. B R E E 4 B ) E M B E D E q u a t i o n . Recall that the attractive energy between two ions is proportional to 1/r, where r is the distance between the ions. Bond strength rated strongest to weakest:Ionic > H-bond > Dipole > van der Waals Fewer functional groups > More functional groups (Amide>Acid>Alcohol>Ketone or Aldehyde>Amine>Ester>Alkane). C a l c u l a t e t h e a m o u n t o f h e a t n e e d e d t o m e l t 2 . 11. In small atoms such as He, the two 1s electrons are held close to the nucleus in a very small volume, and electronelectron repulsions are strong enough to prevent significant asymmetry in their distribution. W h a t t y p e o f c h e m i c a l b o n d h o l d s t h e a t o m s t o g e t h e r w i t h i n a w a t e r m o l e c u l e ? a. Viscosity b. Ans: Category:Medium Section:9.7 44. The first two are often described collectively as van der Waals forces. What kind of attractive forces can exist between nonpolar molecules or atoms? Bodies of water would freeze from the bottom up, which would be lethal for most aquatic creatures. a. water boils at a lower temperature at high altitude than at low altitude h|g CJ UVaJ h>* OJ QJ ^J h>* B*OJ QJ ^J ph "j&. Methane and its heavier congeners in group 14 form a series whose boiling points increase smoothly with increasing molar mass. Compounds with higher molar masses and that are polar will have the highest boiling points. A) Rb2O B) BaO C) SrO D) SeO2 E) MnO2 Ans:D Category:Easy Section:9.4 6. B) polarizability. (iii) Viscosity increases as intermolecular forces increase. These result in much higher boiling points than are observed for substances in which London dispersion forces dominate, as illustrated for the covalent hydrides of elements of groups 1417 in Figure \(\PageIndex{5}\). Use the graph of vapor pressure to determine the normal boiling point of CHCl3. The number of lone electron pairs in the CO32 ion is ___. 1. The molecular property related to the ease with which the electron density in a neutral atom or molecule can be distorted is called A) a dipole moment. Vaporization and more. __________ solids consist of atoms or molecules held together by dipole-dipole forces, London disperson forces, and/or hydrogen bonds. a. Ionic b. Molecular c. Metallic Give the number of lone pairs around the central atom and the molecular geometry of SCl2. D) amorphous solid. There are two additional types of electrostatic interaction that you are already familiar with: the ionion interactions that are responsible for ionic bonding, and the iondipole interactions that occur when ionic substances dissolve in a polar substance such as water. Indicate all the types of intermolecular forces of attraction in C2H6(g). Asked for: order of increasing boiling points. In contrast, the energy of the interaction of two dipoles is proportional to 1/r3, so doubling the distance between the dipoles decreases the strength of the interaction by 23, or 8-fold. Which one of the following derivatives of ethane has the highest boiling point? B) vapor pressure is equal to, or greater than, the external pressure pushing on it. Ans:True Category:Easy Section:10.5 30. A) BrI B) CsI C) LiI D) NaI E) RbI Ans:A Category:Easy Section:11.2 3. Video Discussing Hydrogen Bonding Intermolecular Forces. What condition must exist for a liquid to boil? Which one of the following should have the lowest boiling point? The force of attraction that exists between Na+ and H2O is called a(n) __________ interaction. The strengths of London dispersion forces also depend significantly on molecular shape because shape determines how much of one molecule can interact with its neighboring molecules at any given time. Transitions between the solid and liquid, or the liquid and gas phases, are due to changes in intermolecular interactions, but do not affect intramolecular interactions. h|g h|g B*EHUph jo5(M A) 0 B) +1 C) 1 D) 2 E) +2 Ans:C Category:Difficult Section:9.7 32. Ans: Category:Medium 42. Doubling the distance therefore decreases the attractive energy by 26, or 64-fold. Identify the most significant intermolecular force in each substance. B R E E 4 A n s : B C a t e g o ry:Medium Section:9.2 10. Because the boiling points of nonpolar substances increase rapidly with molecular mass, C 60 should boil at a higher temperature than the other nonionic substances. E) trigonal pyramidal. 0 k J / m o l . b. water boils at a higher temperature at high altitude than at low altitude This molecule has an H atom bonded to an O atom, so it will experience hydrogen bonding. C) molecular crystal. The heat capacity of liquid water is 4.18 J/gC and the heat of vaporization is 40.7 kJ/mol. %, %, %, ] very soft Mark each of the following statements as TRUE or FALSE. Which property of water allows a razor blade to float on it without sinking? Of the species listed, xenon (Xe), ethane (C2H6), and trimethylamine [(CH3)3N] do not contain a hydrogen atom attached to O, N, or F; hence they cannot act as hydrogen bond donors. Which of the atoms listed below is the most electronegative? They need more energy to escape to the gas phase, so the larger molecule has the higher boiling point. h|g CJ UVaJ "j h|g h|g B*EHUph jm5(M According to VSEPR theory, which one of the following molecules should be nonlinear? A hydrogen bond is usually indicated by a dotted line between the hydrogen atom attached to O, N, or F (the hydrogen bond donor) and the atom that has the lone pair of electrons (the hydrogen bond acceptor). Which one of the following is most likely to be a covalent compound? This effect, illustrated for two H2 molecules in part (b) in Figure \(\PageIndex{3}\), tends to become more pronounced as atomic and molecular masses increase (Table \(\PageIndex{2}\)). The more pressure, the more energy is required, so the boiling point is higher at higher pressures. c. cannot go from solid to liquid by application of pressure at any temperature 5 2 4 . A polar covalent bond would form in which one of the following pairs of atoms? The effect is most dramatic for water: if we extend the straight line connecting the points for H2Te and H2Se to the line for period 2, we obtain an estimated boiling point of 130C for water! c. ionic-dipole interactions The predicted order is . At high altitudes, the atmospheric pressure is lower. Small nonpolar molecules Which of the elements listed below is most likely to exhibit an expanded octet in its compounds? The ease of deformation of the electron distribution in an atom or molecule is called its polarizability. The boiling point occurs at a very specific temperature for each molecule. a. can go from solid to liquid, within a small temperature range, via the application of pressure 0 9 J / g C DH f u s = 6 . A) CH4 B) Cl2 C) Kr D) CH3Cl E) N2 Ans:D Category:Medium Section:11.2 7. A) 22.7 kJ B) 40.8 kJ C) 2.2 kJ D) 2,400 J E) 40.8 J Ans:D Category:Medium Section:11.8 23. C) trigonal planar. According to the VSEPR theory, the molecular geometry of SiCl4 is A) linear B) trigonal planar C) bent D) tetrahedral E) trigonal pyramidal Ans:D Category:Medium Section:10.1 10. Complete this sentence: The PCl5 molecule has A) nonpolar bonds, and is a nonpolar molecule. The number of atoms in a body-centered cubic unit cell is A) 1 B) 2 C) 3 D) 4 E) 8 Ans:B Category:Medium Section:11.4 18. 11.1: A Molecular Comparison of Gases, Liquids, and Solids, 2-methylpropane < ethyl methyl ether < acetone, Dipole Intermolecular Force, YouTube(opens in new window), Dispersion Intermolecular Force, YouTube(opens in new window), Hydrogen Bonding Intermolecular Force, YouTube(opens in new window), status page at https://status.libretexts.org. 2 1 2 . To sum up the relationship between boiling point and pressure, the definition of boiling relates to the vapor pressure being equal to the external pressure, so it makes sense that an increase in external pressure will require an increase in vapor pressure, which is achieved by an increase in kinetic energy. A) NF3 B) H2O C) AsCl3 D) GeH4 E) BF3 Ans:E Category:Medium Section:9.9 38. Conversely, \(\ce{NaCl}\), which is held together by interionic interactions, is a high-melting-point solid. Cs 2. e. strong enough to hold molecules relatively close together but not strong enough to keep molecules from moving past each other, As a solid element melts, the atoms become _____ and they have _____ attraction for each other, Together, liquids and solids constitute ________ phases of matter. Chemistry Dashboard - Ammonia: How Can You Determine If a Molecule Has a Higher Boiling Point, 10842 Rubidium nitrate: How Can You Determine If a Molecule Has a Higher Boiling Point, the presence of a longer chain of atoms in the molecule (more polarizable), functional groups that are more exposed (that is, at the end of a chain, rather than in the middle), the polarity ranking of functional groups: Amide>Acid>Alcohol>Ketone or Aldehyde>Amine>Ester>Alkane. Intermolecular forces are electrostatic in nature; that is, they arise from the interaction between positively and negatively charged species. H o w m u c h e n e r g y ( h e a t ) i s r e q u i r e d t o c o n v e r t 5 2 . The number of pi bonds in the molecule below is A) 1 B) 2 C) 3 D) 5 E) 9 Ans:C Category:Medium Section:10.5 26. A) N2O B) CS2 C) PH3 D) CCl4 E) NO2 Ans:E Category:Medium Section:9.9 40. Because molecules in a liquid move freely and continuously, molecules always experience both attractive and repulsive dipoledipole interactions simultaneously, as shown in Figure \(\PageIndex{2}\). Potassium crystallizes in a body-centered cubic lattice. Arrange C60 (buckminsterfullerene, which has a cage structure), NaCl, He, Ar, and N2O in order of increasing boiling points. That is why it is often used to identify an unknown substance in qualitative chemistry. Given the large difference in the strengths of intra- and intermolecular forces, changes between the solid, liquid, and gaseous states almost invariably occur for molecular substances without breaking covalent bonds. The properties of liquids are intermediate between those of gases and solids, but are more similar to solids. The vapor pressure of a liquid in a closed container depends upon A) the amount of liquid. Which one of the following is most likely to be an ionic compound? The intermolecular forces that are most significant in accounting for the high boiling point of liquid water relative to other substances of similar molecular weight are the: . A) CH4 B) CH3Br C) CH3Cl D) CH3F E) CH3I Ans:D Category:Medium Section:10.2 25. C l a s s i f y t h e C C l b o n d i n C C l 4 a s i o n i c , p o l a r c o v a l e n t , o r n o n p o l a r c o v a l e n t . A) Li B) Cs C) P D) As E) Ge Ans:C Category:Medium Section:9.5 17. Of the following, __________ has the highest boiling point. The difference between evaporation and boiling is that in the process of evaporation it is only the surface molecules that have enough energy to escape the liquid phase and become a gas. Legal. @ J K \ ]  & ' 1 2 3 4 @ A , - a b v w x y "j h|g h|g B*EHUph jc5(M Acetic acid has a heat of fusion of 10.8 kJ/mol and a heat of vaporization of 24.3 kJ/mol. Our goal is to make science relevant and fun for everyone. If you are comparing molecules to determine which has the higher boiling point, consider the forces that are at work within the molecule. 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Because ice is less dense than liquid water, rivers, lakes, and oceans freeze from the top down. The expansion of water when freezing also explains why automobile or boat engines must be protected by antifreeze and why unprotected pipes in houses break if they are allowed to freeze. The number of lone electron pairs in the NO2 ion is ___. h|g CJ UVaJ "j h|g h|g B*EHUph jk5(M e. 2and4, The predominant intermolecular force in CaBr2 is __________. On average, the two electrons in each He atom are uniformly distributed around the nucleus. Compounds such as HF can form only two hydrogen bonds at a time as can, on average, pure liquid NH3. h|g CJ UVaJ h>* B*ph h>* j h>* B*Uph "j h|g h|g B*EHUph jh5(M s p e c i f i c h e a t o f i c e : 2 . 1 8 J / g C ; DH f u s = 6 . A) 0 lone pairs, linear D) 3 lone pairs, bent B) 1 lone pair, bent E) 3 lone pairs, linear C) 2 lone pairs, bent Ans:C Category:Medium Section:10.1 2. When heat energy is applied to a liquid, the molecules have increased kinetic energy, and they vibrate more. Larger atoms tend to be more polarizable than smaller ones, because their outer electrons are less tightly bound and are therefore more easily perturbed. h|g CJ UVaJ h>* B*ph h' h>* h>* B*OJ QJ ^J ph j h>* B*Uph "j h|g h|g B*EHUph H I ] ^ _ ` b B D F H L ` d yjXS h>* H*"j) h|g h|g B*EHUph jr5(M Video Discussing Dipole Intermolecular Forces. h|g CJ UVaJ "j h|g h|g B*EHUph je5(M W X l m n o w x whVw "j! The reason for this trend is that the strength of London dispersion forces is related to the ease with which the electron distribution in a given atom can be perturbed. m n x y ) * 4 5 ? In larger atoms such as Xe, however, the outer electrons are much less strongly attracted to the nucleus because of filled intervening shells. Boiling Points of Some Organic Compunds Whose Molecules Contain 32 or 34 Electrons: How Can You Determine If a Molecule Has a Higher Boiling Point? d. not strong enough to keep molecules from moving past each other Butter melts over a range of temperature, rather than with a sharp melting point. Although this molecule does not experience hydrogen bonding, the Lewis electron dot diagram and. Which one of the following molecules has tetrahedral geometry? Which of the elements listed below is the least electronegative? D) square planar. According to VSEPR theory, which one of the following molecules should have a geometry that is trigonal bipyramidal? Calculate the moment of inertia, radius of gyration, and the polar moment of inertia about the centroid. Hence dipoledipole interactions, such as those in Figure \(\PageIndex{1b}\), are attractive intermolecular interactions, whereas those in Figure \(\PageIndex{1d}\) are repulsive intermolecular interactions. a. monoclinic All molecules, whether polar or nonpolar, are attracted to one another by London dispersion forces in addition to any other attractive forces that may be present. A) PBr5 B) CCl4 C) BrF5 D) XeF2 E) XeF4 Ans:C Category:Medium Section:10.2 23. Why do strong intermolecular forces produce such anomalously high boiling points and other unusual properties, such as high enthalpies of vaporization and high melting points? Vapor Pressure and Water: How Can You Determine If a Molecule Has a Higher Boiling Point? In contrast to intramolecular forces, such as the covalent bonds that hold atoms together in molecules and polyatomic ions, intermolecular forces hold molecules together in a liquid or solid. 0 2 k J / m o l s p e c i f i c h e a t o f w a t e r : 4 . Electrostatic interactions are strongest for an ionic compound, so we expect NaCl to have the highest boiling point. Write a Lewis structure for the nitrate ion, NO3, showing all non-zero formal charges. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. a. London-dispersion forces b. ion-dipole attraction c. dipole-dipole attractions d. ion-ion interactions e. none of the above, The predominant intermolecular force in (CH3)2NH is __________. B) ion-dipole forces. Predict the geometry and polarity of the CS2 molecule. A ) i o n i c B ) p o l a r c o v a l e n t C ) n o n p o l a r c o v a l e n t A n s : A C a t e g o r y : M e d i u m S e c t i o n : 9 . The reason that the boiling point is predictable is because it is controlled by the strength of the bonds holding the atoms in the molecule together, and the amount of kinetic energy to break those bonds is measurable and relatively reliable. 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