Give each atom the appropriate formal charge:

Draw a Lewis structure for each of the following species: a. H 2 CO 3 b. CO3 2- c. CH 2 O d. CO

a. Which of the following has a nonpolar covalent bond? b. Which of the following has a bond closest to the ionic end of the bond spectrum? CH3NH2 CH3CH3 CH3F CH3OH

What is the hybridization of all the atoms (other than hydrogen) in each of the following species? What are the bond angles around each atom? a. NH 3 c. -CH3 e. +NH4 g. HCN i. H3O + b. BH 3 d. . CH3 f. +CH3 h. C(CH 3 ) 4 j. H2CO

Draw the condensed structure of a compound that contains only carbon and hydrogen atoms and that has a. three sp3 hybridized carbons. b. one sp3 hybridized carbon and two sp2 hybridized carbons. c. two sp3 hybridized carbons and two sp hybridized carbons.

Predict the approximate bond angles: a. the CiNiC bond angle in (CH 3 )2 + NH2 c. the CiNiH bond angle in (CH 3 ) 2 NH b. the CiOiH bond angle in CH3OH d. the CiNiC bond angle in (CH 3 ) 2 NH

Draw the ground-state electronic coni guration for the following: a. Mg b. Ca2+ c. Ar d. Mg2+

Draw a Lewis structure for each of the following species: a. CH 3 NH 2 b. HNO2 c. N 2 H 4 d. NH2O

What is the hybridization of each of the carbon and oxygen atoms in vitamin C?

List the bonds in order from most polar to least polar. a. CiO , CiF , CiN b. CiCl , CiI , CiBr c. HiO , HiN , HiC d. CiH , CiC , CiN

Draw the Lewis structure for each of the following compounds: a. CH 3 CHO b. CH 3 OCH 3 c. CH 3 COOH

What is the hybridization of the indicated atom in each of the following molecules? a. CH3CH CH2 b. CH3CCH3 O c. CH3CH2OH d. CH3C N e. CH3CH NCH3 f. CH3OCH2CH3

Predict the approximate bond angles for the following: a. the HiCiH bond angle in H2CO c. the CiCiN bond angle in CH3CN b. the FiBiF bond angle in -BF4 d. the CiCiN bond angle in CH 3 CH 2 NH 2

Show the direction of the dipole moment in each of the following bonds (use the electronegativities given in Table 1.3): a. H3CiBr b. H3CiLi c. HOiNH2 d. IiBr e. H3CiOH f. (CH3 )2 NiH

Draw the missing lone-pair electrons and assign the missing formal charges for the following.

a. Which of the indicated bonds in each molecule is shorter? b. Indicate the hybridization of the C, O, and N atoms in each of the molecules.

For each of the following molecules, indicate the hybridization of each carbon and give the approximate values of all the bond angles: a. CH3CCH b. CH3CHCH2 c. CH 3 CH 2 CH 3 d. CH2 CH CH CH2

Draw the Lewis structure for each of the following compounds: a. (CH 3 ) 3 COH b. CH 3 CH(OH)CH 2 CN c. (CH 3 ) 2 CHCH(CH 3 )CH 2 C(CH 3 ) 3

Rank the following compounds from highest dipole moment to lowest dipole moment:

In which orbitals are the lone pairs in nicotine?

Indicate the formal charge on each carbon that has one. All lone pairs are shown.

Do the sp2 carbons and the indicated sp3 carbons lie in the same plane?

a. Which of the species have bond angles of 109.5? b. Which of the species have bond angles of 120?

Which compound has a longer CCl bond?

Which compound has a larger dipole moment, CHCl 3 or CH 2 Cl 2 ?

The following compound has two isomers. One isomer has a dipole moment of 0 D, whereas the other has a dipole moment of 2.95 D. Propose structures for the two isomers that are consistent with these data.

Explain why the following compound is not stable:

Explain why CH 3 Cl has a greater dipole moment than CH 3 F even though F is more electronegative than Cl.

Draw a Lewis structure for each of the following species: a. CH3N2 + b. CH2N2 c. N3 d. N2O (arranged NNO)

Describe the orbitals used in bonding and the bond angles in the following compounds: a. \(\mathrm{CCl}_{4}\) b. \(\mathrm{CO}_{2}\) c. \(\mathrm{HCOOH}\) d. \(N_{2}\) e. \(B F_{3}\) Equation Transcription: Text Transcription: CCl_4 CO_2 HCOOH N_2 BF_3

What is the hybridization of all the atoms (other than hydrogen) in each of the following species? What are the bond angles around each atom? a. \(\mathrm{NH}_{3}\) c. \({ }^{-} \mathrm{CH}_{3}\) e. \({ }^{+} \mathrm{NH}_{4}\) g. \(H C N\) i. \(\mathrm{H}_{3} \mathrm{O}^{+}\) b. \(\mathrm{BH}_{3}\) d. \(\cdot \mathrm{CH}_{3}\) f. \({ }^{+} \mathrm{CH}_{3}\) h. \(\mathrm{C}\left(\mathrm{CH}_{3}\right)_{4}\) j. \(H_{2} C=O\) Equation Transcription: Text Transcription: NH_3 BH_3 ^- CH_3 . CH_3 ^+ NH_4 ^+ CH_3 HCN C(CH_3 )_4 H_3 O^+ H_2 C=O

Problem 49P Draw the condensed structure of a compound that contains only carbon and hydrogen atoms and that has a. three sp3 carbons. b. one sp3 carbon and two sp2 carbons. c. two sp3 carbons and two sp carbons.

Problem 50P Predict the approximate bond angles: a. the C-N-C bond angle in (CH3)2+NH2 c. the C-N-H bond angle in (CH3)2NH b. the C-O-H bond angle in CH3OH d. the C-N-C bond angle in (CH3)2NH

a. Which of the indicated bonds in each molecule is shorter? b. Indicate the hybridization of the \(C, O \text {, and } N\) atoms in each of the molecules. Equation Transcription: Text Transcription: C, O, and N

Problem 61P For each of the following compounds, indicate the hybridization of each carbon atom and give the approximate values of all the bond angles: a. CH3C?CH b. CH3CH = CH2 c. CH3CH2CH3 d. CH2=CH—CH=CH2

Problem 62P Draw the Lewis structure for each of the following compounds: a. (CH3)3COH b. CH3CH(OH)CH2CN c. (CH3)2CHCH(CH3)CH2C(CH3)3

Explain why \(CH_{3}Cl\) has a greater dipole moment than \(CH_{3}F\) even though F is more electronegative than Cl.

Problem 73P Draw a Lewis structure for each of the following species: a. CH3N2+ b. N2 c. N3? d. CH3CONH2

Problem 1P Oxygen has three isotopes with mass numbers of 16, 17, and 18. The atomic number of oxygen is eight. How many protons and neutrons does each of the isotopes have?

Problem 2P Chlorine has two isotopes, 35Cl and 37Cl; 75.77% of chlorine is 35Cl and 24.23% is 37Cl. The atomic mass of 35Cl is 34.969 amu and the atomic mass of 37Cl is 36.966 amu. What is the atomic weight of chlorine?

Problem 3P How many valence electrons do the following atoms have? a. boron b. nitrogen c. oxygen d. fluorine

Give each atom the appropriate formal charge:

Draw the Lewis structure for each of the following: a. \(\mathrm{NO}_{3}-\) c. \({ }^{-} \mathrm{C}_{2} \mathrm{H}_{5}\) e. \(\mathrm{CH}_{3} \mathrm{~N}^{+} \mathrm{H}_{3}\) g. \(\mathrm{HCO}_{3}-\) b. \(\mathrm{NO}_{2}+\) d. \({ }^{+} \mathrm{C}_{2} \mathrm{H}_{5}\) f. \(\mathrm{NaOH}\) h. \(\mathrm{H}_{2} \mathrm{CO}\) Equation Transcription: Text Transcription: NO_3 - NO_2 + ^- C_2 H_5 ^+ C_2 H_5 CH_3 N^+ H_3 NaOH HCO_3 - H_2 CO

Problem 17P a. Draw two Lewis structures for C2H6O. ________________ b. Draw three Lewis structures for C3H8O. (Hint: The two Lewis structures in part a are constitutional isomers; they have the same atoms, but differ in the way the atoms are connected; see page 143. The three Lewis structures in part b arc also constitutional isomers.)

Problem 28P Put a number in each of the blanks: a. ___ s orbital and ___ p orbitals form ____ sp3 orbitals. b. ___ s orbital and ___ p orbitals form ____ sp2 orbitals. c. ___ s orbital and ___ p orbitals form ____ sp orbitals.

For each of the given species: a. Draw its Lewis structure. b. Describe the orbitals used by each carbon atom in bonding and indicate the approximate bond angles. 1. \(\mathrm{H}_{2} \mathrm{CO}\) 2. \(\mathrm{CCl}_{4}\) 3. \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) 4. \(H C N\) Equation Transcription: Text Transcription: H_2 CO CCl_4 CH_3 CO_2 H HCN

Problem 30P Predict the approximate bond angles in a. the methyl cation. b. the methyl radical. c. the methyl anion.

Predict the approximate bond angles for a. the \(\mathrm{C}-\mathrm{N}-\mathrm{C}\) bond angle in \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}_{2}\). b. the \(\mathrm{C}-\mathrm{N}-\mathrm{H}\) bond angle in \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\). c. the \(\mathrm{H}-\mathrm{C}-\mathrm{N}\) bond angle in \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\). d. the \(\mathrm{H}-\mathrm{C}-\mathrm{O}\) bond angle in \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\).

If the dipole moment of \(\mathrm{CH}_{3} \mathrm{F}\) is 1.847 D and the dipole moment of \(\mathrm{CD}_3\mathrm{F}\) is 1.858 D, which is more electronegative, hydrogen or deuterium?

Problem 44P Account for the difference in the shape and color of the potential maps for ammonia and the ammonium ion in Section 1.11.

List the bonds in order from most polar to least polar. a. \(C-O, C-F, C-N\) b. \(C-C l, C-I, C-B r\) c. \(H-O, H-N, H-C\) d. \(C-H, C-C, C-N\) Equation Transcription: Text Transcription: C-O, C-F, C-N C-Cl, C-I, C-Br H-O, H-N, H-C C-H, C-C, C-N

Problem 55P Draw the Lewis structure for each of the following compounds: a. CH3CHO b. CH3OCH3 c. CH3COOH

What is the hybridization of the indicated atom in each of the following molecules?

Do the \(s p^{2}\) carbons and the indicated \(s p^{3}\) carbons lie in the same plane? Equation Transcription: Text Transcription: sp^2 sp^3

a. Which of the species have bond angles of 109.5°? b. Which of the species have bond angles of 120°? \(\begin{array}{lllllll}\mathrm{H}_2\mathrm{O}&\mathrm{H}_3\mathrm{O}^+&^+\mathrm{CH}_3&\mathrm{BF}_3&\mathrm{NH}_3&^+\mathrm{NH}_4&^-\mathrm{CH}_3\end{array}\)

Which compound has a longer \(C-C l\) bond? \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\) \(\mathrm{CH}_{2}=\mathrm{CHCl}\) at one time it was used as a used as the starting material refrigerant, an anesthetic, and a for the synthesis of a plastic that propellant for aerosol sprays is used to make bottles, ooring, and clear packaging for food Equation Transcription: Text Transcription: C-Cl CH_3 CH_2 Cl CH_2 = CHCl

Problem 4P a. Write electronic configurations for chlorine (atomic number 17), bromine (atomic number 35), and iodine (atomic number 53). b. How many valence electrons do chlorine, bromine, and iodine have?

Problem 5P Look at the relative positions of each pair of atoms listed here in the periodic table. How many core electrons does each have? How many valence electrons does each have? a. carbon and silicon c. nitrogen and phosphorus b. oxygen and sulfur d. magnesium and calcium

Problem 6P a. Find potassium (K) in the periodic table and predict how many valence electrons it has. b. What orbital does the unpaired electron occupy?

Draw the lone-pair electrons that are not shown in the following condensed structures: a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) e. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\) b. \(\mathrm{CH}_{3} \mathrm{NHCH}_{3}\) d. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) f. \(\mathrm{HONH}_{2}\) Equation Transcription: Text Transcription: CH_3 CH_2 NH_2 CH_3 NHCH_3 CH_3 CH_2 OH CH_3 OCH_3 CH_3 CH_2 Cl HONH_2

Draw condensed structures for the compounds represented by the following models (black = \(C\), gray = \(H\), red = \(O\), blue = \(N\), and green = \(\mathrm{Cl}\)): Equation Transcription: Text Transcription: C H O N Cl

Problem 20P Which of the atoms in the molecular models in Problem 19 have a. three lone pairs? b. two lone pairs? c. one lone pair? d. no lone pairs?

Problem 31P According to the potential map for the ammonium ion, which atom has the greatest electron density?

Compare the potential maps for methane, ammonia, and water. Which is the most polar molecule? Which is the least polar?

Problem 34P a. Predict the relative lengths and strengths of the bonds in Cl2 and Br2. b. Predict the relative lengths and strengths of the carbon-halogen bonds in CH3F, CH3Cl, and CH3Br.

Which of the following molecules would you expect to have a dipole moment of zero? To answer parts g and h, you may need to review the Problem Solving Strategy on page 42. a. \(\mathrm{CH}_{3} \mathrm{CH}_{3}\) c. \(\mathrm{CH}_{2} \mathrm{Cl}_{2}\) e. \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}_{2}\) g. \(\mathrm{BeCl}_{2}\) b. \(H_{2} C=O\) d. \(\mathrm{NH}_{3}\) f. \(H_{2} C=C H B r\) h. \(B F_{3}\) Equation Transcription: Text Transcription: CH_3 CH_3 H_2 C=O CH_2 Cl_2 NH_3 H_2 C = CH_2 H_2 C = CHBr BeCl_2 BF_3

Problem 46P Draw a Lewis structure for each of the following species: a. H2CO3 b. CO32- c. CH2O d. CO2

a. Which of the following has a nonpolar covalent bond? b. Which of the following has a bond closest to the ionic end of the bond spectrum? \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) \(\mathrm{CH}_{3} \mathrm{CH}_{3}\) \(\mathrm{CH}_3\mathrm{F}\) \(\mathrm{CH}_{3} \mathrm{OH}\)

Predict the approximate bond angles for the following: a. the \(H-C-H\) bond angle in \(H_{2} C=O\) c. the \(C-C-N\) bond angle in \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{N}\) b. the \(F-B-F\) bond angle in \({ }^{-} B F_{4}\) d. the \(C-C-N\) bond angle in \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) Equation Transcription: ? Text Transcription: H-C-H H_2 C = O F-B-F ^- BF_4 C-C-N CH_3 C trigram N CH_3 CH_2 NH_2

Show the direction of the dipole moment in each of the following bonds (use the electronegativities given in Table 1.3): a. \(H_{3} C-B r\) b. \(H_{3} C-L i\) c. \(\mathrm{HO}-\mathrm{NH}_{2}\) d. \(l-B r\) e. \(\mathrm{H}_{3} \mathrm{C}-\mathrm{OH}\) f. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{~N}-\mathrm{H}\) Equation Transcription: Text Transcription: H_3 C-Br H_3 C-Li HO-NH_2 l-Br H_3 C-OH (CH_3 )_2 N-H

Draw the missing lone-pair electrons and assign the missing formal charges for the following.

Which compound has a larger dipole moment, \(CHCl_{3}\) or \(CH_{2}Cl_{2}\)?

Problem 70P The following compound has two isomers. One isomer has a dipole moment of 0 D, whereas the other has a dipole moment of 2.95 D. Propose structures for the two isomers that are consistent with these data. ClCH=CHCl

Explain why the following compound is not stable:

Which bond is more polar? a. H—\(\mathrm{CH}_{3}\) or Cl—\(\mathrm{CH}_{3}\) b. H—OH or H—H c. H—Cl or H—F d. Cl—Cl or Cl—\(\mathrm{CH}_{3}\)

Which of the following has a. the most polar bond? b. the least polar bond? \(\begin{array}{llll} \text { Nal } & \text { LiBr } & \mathrm{Cl}_{2} & \mathrm{KCl} \end{array}\) Equation Transcription: Text Transcription: Nal LiBr C1_2 KC1

Use the symbols \(\delta^{+} \text {and } \delta^{-}\) to show the direction of the polarity of the indicated bond in each of the following compounds: a. \(H O-H\) c. \(H_{3} \mathrm{C}-\mathrm{NH}_{2}\) e. \(H O-B r\) g. \(l-C 1\) b. \(F-B r\) d. \(H_{3} C-C 1\) f. \(H_{3} C-L i\) h. \(\mathrm{H}_{2} \mathrm{~N}-\mathrm{OH}\) Equation Transcription: Text Transcription: delta^+ and delta^- HO-H F-Br H_3 C-NH_2 H_3 C-NH_2 H_3 C-C1 HO-Br H_3 C-Li l-C1 H_2 N-OH

Expand the following condensed structures to show the covalent bonds and lone-pair electrons: a. \(\mathrm{CH}_{3} \mathrm{NH}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}_{3}\) b. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl}\) c. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}\) d. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{CHO}\) Equation Transcription: Text Transcription: CH_3 NH(CH_2 )_2 CH_3 (CH_3 )_2 CHC1 (CH_3 )_3 CBr (CH_3 )_3 C(CH_2 )_3 CHO

Problem 22P Draw a picture of a. a 3s orbital. b. a 4s orbital. c. a 3p orbital.

Problem 23P Predict whether or not He2 + exists.

Problem 35P a. Which bond would be longer? b. Which bond would be stronger? 1 . C-Cl or C-I 2. C-C or C-Cl 3. H-Cl or H-F

Problem 38P Which of the bonds in a carbon-oxygen double bond has more effective orbital-orbital overlap, the sigma bond or the pi bond?

Problem 12P Explain why HCl has a smaller dipole moment than HF, even though the H-Cl bond is longer than the H-F bond.

Problem 13P After examining the potential maps for LiH, HF, and H2, answer the following questions: a. Which compounds are polar? b. Why does LiH have the largest hydrogen? c. Which compound has the hydrogen that would be most apt to attract a negatively charged molecule?

Problem 14P The formal charge does not necessarily indicate that the atom has greater or less electron density than other atoms in the molecule without formal charges. You can see this by ex­amining the potential maps for H20, H30+, and HO?. a. Which atom bears the formal negative charge in the hydroxide ion? ________________ b. Which atom has the greater electron density in the hydroxide ion? ________________ c. Which atom bears the formal positive charge in the hydronium ion? ________________ d. Which atom has the least electron density in the hydronium ion?

Indicate the kind of molecular orbital \(\left(\sigma, \sigma^{*}, \pi, O r \pi^{*}\right)\) that results when atomic orbitals are combined as indicated: Equation Transcription: Text Transcription: (sigma, sigma^* , pi, or pi^* )

Problem 25P What orbitals are used to form the 10 covalent bonds in propane (CH3CH2CH3)?

Problem 26P Explain why a sigma bond formed by overlap of an s orbital with an sp3 orbital of carbon is stronger than a sigma bond formed by overlap of an s orbital with a p orbital of carbon.

Problem 39P Would you expect a C-C sigma bond formed by sp2-sp2 overlap to be stronger or weaker than a C-C sigma bond formed by sp3-sp3 overlap?

Caffeine is a natural insecticide, found in the seeds and leaves of certain plants, where it kills insects that feed on the plant. Caffeine is extracted for human consumption from beans of the coffee plant, from Kola nuts, and from the leaves of tea plants. Because it stimulates the central nervous system, it temporarily prevents drowsiness. Add caffeine’s missing lone pairs to its structure.

a. What is the hybridization of each of the carbon atoms in the following compound? b. What is the hybridization of each of the atoms in Demerol and Prozac? c. Which two atoms form an ionic bond in Prozac?

Problem 51P Draw the ground-state electronic configuration for the following: a. Mg b. Ca2+ c. Ar d. Mg2+

Problem 52P Draw a Lewis structure for each of the following species: a. CH3NH2 b. HNO2 c. N2H4 d. NH2O-

What is the hybridization of each of the carbon and oxygen atoms in vitamin \(C\)? Equation Transcription: Text Transcription: C

Rank the following compounds from highest dipole moment to lowest dipole moment:

In which orbitals are the lone pairs in nicotine?

Indicate the formal charge on each carbon that has one. All lone pairs are shown.