Propose skeletal structures for compounds that satisfy the

Give the ground-state electron configuration for each of the following elements: (a) Oxygen (b) Nitrogen (c) Sulfur

How many electrons does each of the following elements have in its outermost electron shell? (a) Magnesium (b) Cobalt (c) Selenium

How many hydrogen atoms does phosphorus bond to in forming phosphine, \(\mathrm{PH_?}\)? ________________ Equation Transcription: Text Transcription: PH_?

Draw a molecule of chloroform, \(\mathrm{CHCl_3}\), using solid, wedged, and dashed lines to show its tetrahedral geometry. ________________ Equation Transcription: Text Transcription: CHCl_3

Convert the following representation of ethane, \(\mathrm{C_2H_6}\), into a conventional drawing that uses solid, wedged, and dashed lines to indicate tetrahedral geometry around each carbon (gray = C, ivory = H). ________________ Equation Transcription: Text Transcription: C_2H_6

What are likely formulas for the following substances? (a) \(\mathrm{CCl_?}\) (b) \(\mathrm{AlH_?}\) (c) \(\mathrm{CH_?Cl_2}\) (d) \(\mathrm{SiF_?}\) (e) \(\mathrm{CH3NH_?}\) ________________ Equation Transcription: Text Transcription: CCl_? AlH_? CH_?Cl_2 SiF_? CH_3NH_?

Write line-bond structures for the following substances, showing all nonbonding electrons: (a) \(\mathrm{CHCl_3}\), chloroform (b) \(\mathrm{H_2S}\), hydrogen sulfide (c) \(\mathrm{CH_3NH_2}\), methylamine (d) \(\mathrm{CH_3Li}\), methyllithium ________________ Equation Transcription: Text Transcription: CHCl_3 CH_3NH_2 H_2S CH_3Li

Why can’t an organic molecule have the formula \(\mathrm{C_2H_7}\)? ________________ Equation Transcription: Text Transcription: C_2H_7

Draw a line-bond structure for propane, \(\mathrm{CH_3CH_2CH_3}\). Predict the value of each bond angle, and indicate the overall shape of the molecule. ________________ Equation Transcription: Text Transcription: CH_3CH_2CH_3

Convert the following molecular model of hexane, a component of gasoline, into a line-bond structure (gray = C, ivory = H).

Draw a line-bond structure for propene, \(\mathrm{CH_3CH=CH_2}\). Indicate the hybridization of the orbitals on each carbon, and predict the value of each bond angle. ________________ Equation Transcription: Text Transcription: CH_3CH=CH_2

Draw a line-bond structure for 1,3-butadiene, \(\mathrm{H_2C=CH-CH=CH_2}\). Indicate the hybridization of the orbitals on each carbon, and predict the value of each bond angle. ________________ Equation Transcription: Text Transcription: H_2C=CH-CH=CH_2

Following is a molecular model of aspirin (acetylsalicylic acid). Identify the hybridization of the orbitals on each carbon atom in aspirin, and tell which atoms have lone pairs of electrons (gray =C, red = O, ivory = H).

Draw a line-bond structure for propyne, \(\mathrm{CH_3C \equiv CH}\). Indicate the hybridization of the orbitals on each carbon, and predict a value for each bond angle. ________________ Equation Transcription: Text Transcription: CH_3C equiv CH

Identify all nonbonding lone pairs of electrons in the following molecules, and tell what geometry you expect for each of the indicated atoms. (a) The oxygen atom in dimethyl ether, \(\mathrm{CH_3-O-CH}\) (b) The nitrogen atom in trimethylamine, (c) The phosphorus atom in phosphine, \(\mathrm{PH_3}\) (d) The sulfur atom in the amino acid methionine, ________________ Equation Transcription: Text Transcription: CH_3-O-CH_3 H_3C-N-CH_3 CH_3 PH_3 CH_3-S-CH_2CH_2CHCOH NH_2

Tell how many hydrogens are bonded to each carbon in the following compounds, and give the molecular formula of each substance: ________________ Equation Transcription: Text Transcription: NHCH_3

Propose skeletal structures for compounds that satisfy the following molecular formulas. There is more than one possibility in each case. (a) \(\mathrm{C_5H_{12}}\) (b) \(\mathrm{C_2H_7N}\) (c) \(\mathrm{C_3H_6O}\) (d) \(\mathrm{C_4H_9Cl}\) ________________ Equation Transcription: Text Transcription: C_5H_12 C_2H_7N C_3H_6O C_4H_9Cl

The following molecular model is a representation of para-aminobenzoic acid (PABA), the active ingredient in many sunscreens. Indicate the positions of the multiple bonds, and draw a skeletal structure (gray = C, red = O, blue = N, ivory = H).

Convert each of the following molecular models into a skeletal structure, and give the formula of each. Only the connections between atoms are shown; multiple bonds are not indicated (gray = C, red = O, blue = N, ivory = H).

The following model is a representation of citric acid, the key substance in the so-called citric acid cycle, by which food molecules are metabolized in the body. Only the connections between atoms are shown; multiple bonds are not indicated. Complete the structure by indicating the positions of multiple bonds and lone-pair electrons (gray = C, red = O, ivory = H).

The following model is a representation of acetaminophen, a pain reliever sold in drugstores under a variety of names, including Tylenol. Identify the hybridization of each carbon atom in acetaminophen, and tell which atoms have lone pairs of electrons (gray = C, red = O, blue = N, ivory = H).

The following model is a representation of aspartame, \(\mathrm{C_{14}H_{18}N_2O_5}\), known commercially under many names, including NutraSweet. Only the connections between atoms are shown; multiple bonds are not indicated. Complete the structure for aspartame, and indicate the positions of multiple bonds (gray = C, red = O, blue = N, ivory = H). ________________ Equation Transcription: Text Transcription: C_{14}H_{18}N_2O_5

How many valence electrons does each of the following dietary trace elements have? (a) Zinc (b) Iodine (c) Silicon (d) Iron

Give the ground-state electron configuration for each of the following elements: (a) Potassium (b) Arsenic (c) Aluminum (d) Germanium

What are likely formulas for the following molecules? (a) \(\mathrm {NH_?OH}\) (b) \(\mathrm {AlCl_?}\) (c) \(\mathrm {CF_2Cl_?}\) (d) \(\mathrm {CH_?O}\) ________________ Equation Transcription: Text Transcription: NH_?OH AlCl_? CF_2Cl_? CH_?O

Why can’t molecules with the following formulas exist? (a) \(\mathrm {CH_5}\) (b) \(\mathrm {C_2H_6N}\) (c) \(\mathrm {C_3H_5Br_2}\) ________________ Equation Transcription: Text Transcription: CH_5 C_2H_6N C_3H_5Br_2

Draw an electron-dot structure for acetonitrile, \(\mathrm {C_2H_3N}\), which contains a carbon–nitrogen triple bond. How many electrons does the nitrogen atom have in its outer shell? How many are bonding, and how many are nonbonding? ________________ Equation Transcription: Text Transcription: C_2H_3N

Draw a line-bond structure for vinyl chloride, \(\mathrm {C_2H_3Cl}\), the starting material from which PVC [poly(vinyl chloride)] plastic is made. ________________ Equation Transcription: Text Transcription: C_2H_3Cl

Fill in any nonbonding valence electrons that are missing from the following structures: ________________ Equation Transcription: Text Transcription: H_3C CH_3 H_3C NH_2 H_3C O^-

Convert the following line-bond structures into molecular formulas: ________________ Equation Transcription: Text Transcription: CH_3 CH_2OH CH_3 CH_2OH

Convert the following molecular formulas into line-bond structures that are consistent with valence rules: (a) \(\mathrm {C_3H_8}\) (b) \(\mathrm {CH_5N}\) (c) \(\mathrm {C_2H_6O}\) (2 possibilities) (d) \(\mathrm {C_3H_7Br}\) (2 possibilities) (e) \(\mathrm {C_2H_4O}\) (3 possibilities) (f) \(\mathrm {C_3H_9N}\) (4 possibilities) ________________ Equation Transcription: Text Transcription: C_3H_8 CH_5N C_2H_6O C_3H_7Br C_2H_4O C_3H_9N

Draw a three-dimensional representation of the oxygen-bearing carbon atom in ethanol, \(\mathrm {CH_3CH_2OH}\), using the standard convention of solid, wedged, and dashed lines. ________________ Equation Transcription: Text Transcription: CH_3CH_2OH

Oxaloacetic acid, an important intermediate in food metabolism, has the formula \(\mathrm {C_4H_4O_5}\) and contains three C=O bonds and two \(\mathrm {O-H}\) bonds. Propose two possible structures. ________________ Equation Transcription: Text Transcription: C_4H_4O_5

Draw structures for the following molecules, showing lone pairs: (a) Acrylonitrile, \(\mathrm {C_3H_3N}\), which contains a carbon–carbon double bond and a carbon–nitrogen triple bond (b) Ethyl methyl ether, \(\mathrm {C_3H_8O}\), which contains an oxygen atom bonded to two carbons (c) Butane, \(\mathrm {C_4H_{10}}\), which contains a chain of four carbon atoms (d) Cyclohexene, \(\mathrm {C_6H_{10}}\), which contains a ring of six carbon atoms and one carbon–carbon double bond ________________ Equation Transcription: Text Transcription: C_3H_3N C_3H_8O C_4H_{10} C_6H_{10}

Potassium methoxide, \(\mathrm {KOCH_3}\), contains both covalent and ionic bonds. Which do you think is which? ________________ Equation Transcription: Text Transcription: KOCH_3

What is the hybridization of each carbon atom in acetonitrile (Problem 1-26)?

What kind of hybridization do you expect for each carbon atom in the following molecules? ________________ Equation Transcription: Text Transcription: CH_3CH_2CH_3 CH_3 CH_3C=CH_2 H_2C=CH-CCH CH_3COH

What is the shape of benzene, and what hybridization do you expect for each carbon?

What bond angles do you expect for each of the following, and what kind of hybridization do you expect for the central atom in each?

Propose structures for molecules that meet the following descriptions: (a) Contains two \(sp^2\)-hybridized carbons and two \(sp^3\)-hybridized carbons (b) Contains only four carbons, all of which are \(sp^2\)-hybridized (c) Contains two \(sp\)-hybridized carbons and two \(sp^2\)-hybridized carbons ________________ Equation Transcription: Text Transcription: sp^2 sp^3 sp^2 sp^2

What kind of hybridization do you expect for each carbon atom in the following molecules? ________________ Equation Transcription: Text Transcription: H_2N CH_2 CH_2 CH_2-CH_3 CH_2-CH_3 ^+N CH_2OH

Pyridoxal phosphate, a close relative of vitamin \(\mathrm {B_6}\), is involved in a large number of metabolic reactions. Tell the hybridization, and predict the bond angles for each nonterminal atom. ________________ Equation Transcription: Text Transcription: B_6 H_3C O^- O^-

Convert the following structures into skeletal drawings:

Tell the number of hydrogens bonded to each carbon atom in the following substances, and give the molecular formula of each:

Quetiapine, marketed as Seroquel, is a heavily prescribed antipsychotic drug used in the treatment of schizophrenia and bipolar disorder. Convert the following representation into a skeletal structure, and give the molecular formula of quetiapine. ________________ Equation Transcription: Text Transcription: OCH_2CH_2OCH_2CH_2OH H_2C H_2C CH_2 CH_2

Tell the number of hydrogens bonded to each carbon atom in (a) the antiinfluenza agent oseltamivir, marketed as Tamilu, and (b) the platelet aggregation inhibitor clopidogrel, marketed as Plavix. Give the molecular formula of each. ________________ Equation Transcription: Text Transcription: NH_2

Why do you suppose no one has ever been able to make cyclopentyne as a stable molecule?

Allene, \(\mathrm {H_2C=C=CH_2}\), is somewhat unusual in that it has two adjacent double bonds. Draw a picture showing the orbitals involved in the \(\sigma\) and \(\pi\) bonds of allene. Is the central carbon atom \(sp^2\)- or \(sp\)-hybridized? What about the hybridization of the terminal carbons? What shape do you predict for allene? ________________ Equation Transcription: Text Transcription: H_2C=C=CH_2 sigma pi sp^2

Allene (see Problem 1-47) is structurally related to carbon dioxide, \(\mathrm {CO_2}\). Draw a picture showing the orbitals involved in the \(\sigma\) and \(\pi\) bonds of\(\mathrm {CO_2}\), and identify the likely hybridization of carbon. ________________ Equation Transcription: Text Transcription: CO_2 sigma pi CO_2

Complete the electron-dot structure of caffeine, showing all lone-pair electrons, and identify the hybridization of the indicated atoms. ________________ Equation Transcription: Text Transcription: H_3C CH_3 CH_3

Most stable organic species have tetravalent carbon atoms, but species with trivalent carbon atoms also exist. Carbocations are one such class of compounds. (a) How many valence electrons does the positively charged carbon atom have? (b) What hybridization do you expect this carbon atom to have? (c) What geometry is the carbocation likely to have? ________________ Equation Transcription: Text Transcription: C^+

A carbanion is a species that contains a negatively charged, trivalent carbon. (a) What is the electronic relationship between a carbanion and a trivalent nitrogen compound such as \(\mathrm {NH_3}\)? (b) How many valence electrons does the negatively charged carbon atom have? (c) What hybridization do you expect this carbon atom to have? (d) What geometry is the carbanion likely to have? ________________ Equation Transcription: Text Transcription: C:^- NH_3

Divalent carbon species called carbenes are capable of fleeting existence. For example, methylene, :\(\mathrm {CH_2}\), is the simplest carbene. The two unshared electrons in methylene can be either paired in a single orbital or unpaired in different orbitals. Predict the type of hybridization you expect carbon to adopt in singlet (spin-paired) methylene and triplet (spin-unpaired) methylene. Draw a picture of each, and identify the valence orbitals on carbon. ________________ Equation Transcription: Text Transcription: CH_2

There are two different substances with the formula \(\mathrm {C_4H_{10}}\). Draw both, and tell how they differ. ________________ Equation Transcription: Text Transcription: C_4H_{10}

There are two different substances with the formula \(\mathrm {C_3H_6}\). Draw both, and tell how they differ. ________________ Equation Transcription: Text Transcription: C_3H_6

There are two different substances with the formula \(\mathrm {C_2H_6O}\). Draw both, and tell how they differ. ________________ Equation Transcription: Text Transcription: C_2H_6O

There are three different substances that contain a carbon–carbon double bond and have the formula \(\mathrm {C_4H_8}\). Draw them, and tell how they differ. ________________ Equation Transcription: Text Transcription: C_4H_8

Among the most common over-the-counter drugs you might find in a medicine cabinet are mild pain relievers such ibuprofen (Advil, Motrin), naproxen Aleve), and acetaminophen (Tylenol). (a) How many \(sp^3\)-hybridized carbons does each molecule have? (b) How many \(sp^2\)-hybridized carbons does each molecule have? (c) Can you spot any similarities in their structures? ________________ Equation Transcription: Text Transcription: H_3C CH_3 sp^3 sp^2