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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

A promising new material with great potential as a fuel in solid rocket motors is ammonium dinitramide [NH4N(NO2)2]. a. Draw Lewis structures (including resonance forms) for the dinitramide ion
Think of forming an ionic compound as three steps (this is a simplification, as with all models): (1) Removing an electron from the metal (2) Adding an electron to the nonmetal (3) Allowing the
The compound hexaazaisowurtzitane is one of the highest- energy explosives known (C & E News, p. 26, Jan. 17, 1994). The compound, also known as CL-20, was first synthesized in 1987. The method of
In molecules of the type X–O–H, as the electronegativity of X increases, the acid strength increases. In addition, if the electronegativity of X is a very small value, the molecule acts like a
Calculate the standard heat of formation of the compound ICl (g) at 25oC.Table
An ionic compound made from the metal M and the diatomic gas X2 has the formula MaXb, in which a = 1 or 2 and b = 1 or 2. Use the data provided to determine the most likely values for a and b, along
Identify the following five compounds of H, N, and O. For each compound, write a Lewis structure that is consistent with the information given. a. All the compounds are electrolytes, although not all
Why do we hybridize atomic orbitals to explain the bonding in covalent compounds? What type of bonds form from hybrid orbitals, σ or π? Explain.
What hybridization is required for central atoms that have a tetrahedral arrangement of electron pairs? A trigonal planar arrangement of electron pairs? A linear arrangement of electron pairs? How
Why are d orbitals sometimes used to form hybrid orbitals? Which period of elements does not use d orbitals for hybridization? If necessary, which d orbitals (3d, 4d, 5d, or 6d) would sulfur use to
The atoms in a single bond can rotate about the internuclear axis without breaking the bond. The atoms in a double bond and a triple bond cannot rotate about the internuclear axis unless the bond is
Use the LE model to describe the bonding in H2O.
Use the LE model to describe the bonding in H2CO and C2H2. Carbon is the central atom in H2CO, and C2H2 exists as HCCH.
The space-filling models of ethane and ethanol are shown below.Use the LE model to describe the bonding in ethane and ethanol.
The space-filling models of hydrogen cyanide and phosgene are shown below.Use the LE model to describe the bonding in hydrogen cyanide and phosgene.
Give the expected hybridization of the central atom for the molecules or ions in Exercises 57, 58, and 60 from Chapter 13.
Give the expected hybridization of the central atom for the molecules in Exercises 91 and 92 from Chapter 13.
Urea, a compound formed in the liver, is one of the ways humans excrete nitrogen. The Lewis structure for urea isUsing hybrid orbitals for carbon, nitrogen, and oxygen, determine which orbitals
Give the expected hybridization for the molecular structures illustrated below.
For each of the following molecules, write a Lewis structure, predict the molecular structure (including bond angles), give the expected hybrid orbitals on the central atom, and predict the overall
Predict the hybrid orbitals used by the sulfur atom(s) in each of the following. Also predict the molecular structure, including bond angle(s).a. SO2b. SO3e. SO32- f. SO42- g. SF2 h. SF4 i. SF6 j.
Why must all six atoms in C2H4 be in the same plane?
The allene molecule has the following Lewis structure:Must all four hydrogen atoms lie in the same plane? If not, what is the spatial relationship among them? Why?
Biacetyl and acetoin are added to margarine to make it taste more like butter.Complete the Lewis structures, predict values for all C€“C€“O bond angles, and give the hybridization
Many important compounds in the chemical industry are derivatives of ethylene (C2H4). Two of them are acrylonitrile and methyl methacrylate.Complete the Lewis structures for these molecules, showing
One of the first drugs to be approved for use in treatment of acquired immune deficiency syndrome (AIDS) was azidothymidine (AZT). Complete the Lewis structure of AZT.a. How many carbon atoms use sp3
Hot and spicy foods contain molecules that stimulate pain- detecting nerve endings. Two such molecules are piperine and capsaicin:Piperine is the active compound in white and black pep-per, and
Two molecules used in the polymer industry are azodicarbonamide and methyl cyanoacrylate. Their structures areAzodicarbonamide is used in forming polystyrene. When added to the molten plastic, it
The antibiotic thiarubin-A was discovered by studying the feeding habits of wild chimpanzees in Tanzania. The structure for thiarubin-A isa. Complete the Lewis structures showing all lone pairs of
The three most stable oxides of carbon are carbon monoxide (CO), carbon dioxide (CO2), and carbon suboxide (C3O2). The space- filling models for these three com-pounds areFor each oxide, draw the
Consider the following molecular orbitals formed from the combination of two hydrogen 1s orbitals:a. Which is the bonding molecular orbital, and which is the antibonding molecular orbital? Explain
Sketch the molecular orbital and label its type (Ïƒ or p; bonding or antibonding) that would be formed when the following atomic orbitals overlap. Explain your labels.
What are the relationships among bond order, bond energy, and bond length? Which of these can be measured? Distinguish between the terms paramagnetic and diamagnetic. What type of experiment can be
What modification to the molecular orbital model was made from the experimental evidence that B2 is paramagnetic?
A Lewis structure obeying the octet rule can be drawn for O2 as follows:Use the molecular orbital energy- level diagram for O2 to show that the above Lewis structure corresponds to an exicted state.
How does molecular orbital theory explain the following observations? a. H2 is stable, whereas He2 is unstable. b. B2 and O2 are paramagnetic, whereas C2, N2, and F2 are diamagnetic. c. N2 has a very
Why does the molecular orbital model do a better job in explaining the bonding in NO- and NO than the hybrid orbital model?
Show how a hydrogen 1s atomic orbital and a fluorine 2p atomic orbital overlap to form bonding and antibonding MOs in the hydrogen fluoride molecule. Are they σ or π MOs?
Which of the following are predicted by the molecular orbital model to be stable diatomic species? a. H2+, H2, H2-, H22- b. N22-, O22-, F22- c. Be2, B2, Ne2
Which charge(s) for the N2 molecule would give a bond order of 2.5?
In which of the following diatomic molecules would the bond strength be expected to weaken as an electron is removed? H2 B2 C22- OF
In terms of the molecular orbital model, which species in each of the following two pairs will most likely be the one to gain an electron? Explain. CN or NO, O22+ or N22+
Using the molecular orbital model to describe the bonding in CO, CO+, and CO2+, predict the bond orders and the relative bond lengths for these three species. How many unpaired electrons are present
Consider the following electron configuration: (σ3σ) 2(σ3σ*) 2(σ3π) 2(π3π) 4(πsπ*) 4 Give four species that, in theory, would have this electron configuration.
Using an MO energy- level diagram, would you expect O2 to have a lower or higher first ionization energy than atomic oxygen? Why?
Use Figs. 45 and 46 to answer the following questions.a. Would the bonding MO in HF place greater electron density near the H or the F atom? Why?b. Would the bonding MO have greater fluorine 2p
The diatomic molecule OH exists in the gas phase. OH plays an important part in combustion reactions and is a reactive oxidizing agent in polluted air. The bond length and bond energy have been
What is delocalized π bonding, and what does it explain? Explain the delocalized π bonding system in C6H6 (benzene) and SO2.
Describe the bonding in the O3 molecule and the NO2- ion using the LE model. How would the molecular orbital model describe the π bonding in these two species?
Describe the bonding in the CO32- ion using the LE model. How would the molecular orbital model describe the π bonding in this species?
The space- filling model for benzoic acid is shown below.Describe the bonding in benzoic acid using the LE model combined with the molecular orbital model.
The infrared spectrum of 1H79Br shows the y = 0 to y = 1 transition at 2650 cm-1. Determine the vibrational force constant for the HBr molecule. The atomic mass of 1H is 1.0078 amu, and the atomic
If the force constant of 14N16O is 1550. Nm-1, determine the wave number of a line in the infrared spectrum of NO. The atomic mass of 14N is 14.003 amu, and the atomic mass of 16O is 15.995 amu.
The microwave spectrum of 12C16O shows that the transition from J = 0 to J = 1 requires electromagnetic radiation with a wavelength of 2.60 × 10-3 m. a. Calculate the bond length of CO. See Exercise
Draw the idealized NMR spectra for the following compounds.Assume that the five hydrogen atoms in the benzene ring are equivalent with no spin€“spin coupling.
Consider the following idealized NMR multiplets.Which is the correct multiplet for the underlined group in the following molecules?
The NMR spectra below are for the organic compounds C6H12 and C4H10O. Deduce the structures for these compounds. See Exercise 70 for a discussion of the bonding in organic compounds. The structure of
Draw the Lewis structures, predict the molecular structures, and describe the bonding (in terms of the hybrid orbitals for the central atom) for the following. a. XeO3 b. XeO4 c. XeOF4 d. XeOF2 e.
FClO2 and F3ClO can both gain a fluoride ion to form stable anions. F3ClO and F3ClO2 can also lose a fluoride ion to form stable cations. Draw Lewis structures and describe the hybrid orbitals used
Two structures can be drawn for cyanuric acid:a. Are these two structures the same molecule? Why or why not? b. Give the hybridization of the carbon and nitrogen atoms in each structure. c. Use bond
Using bond energies from Table, estimate the barrier to rotation around a carbon€“carbon double bond. To do this, consider what must happen to go fromIn terms of making and breaking
Show how a dxz atomic orbital and a pz atomic orbital combine to form a bonding molecular orbital. Assume the x axis is the internuclear axis. Is a σ or a π molecular orbital formed? Explain.
Describe the bonding in the first excited state of N2 (the one closest in energy to the ground state) using the MO model. What differences do you expect in the properties of the molecule in the
Consider three molecules: A, B, and C. Molecule A has a hybridization of sp3. Molecule B has two more effective pairs (electron pairs around the central atom) than molecule A. Molecule C consists of
Complete the following resonance structures for POCl3:a. Would you predict the same molecular structure from each resonance structure? b. What is the hybridization of Ï€ in each
Complete the Lewis structures of the following molecules. Predict the molecular structure, polarity, bond angles, and hybrid orbitals used by the atoms marked by asterisks for each molecule.
Vitamin B6 is an organic compound whose deficiency in the human body can cause apathy, irritability, and an in-creased susceptibility to infections. Below is an incomplete Lewis structure, for
Consider the following computer- generated model of caffeine:Complete a Lewis structure for caffeine in which all atoms have a formal charge of zero (as is typical with most organic compounds). How
Aspartame is an artificial sweetener marketed under the name Nutra-Sweet. A partial Lewis structure for aspartame is shown below:Note that the six- sided ring is shorthand notation for a benzene ring
The N2O molecule is linear and polar.a. On the basis of this experimental evidence, which arrangement is correct, NNO or NON? Explain your answer.b. On the basis of your answer in part a, write the
Values of measured bond energies may vary greatly depending on the molecule studied. Consider the following reactions: NCl3(g) → NCl2(g) + Cl(g) ΔH = 375 kJ/ mol ONCl(g) → NO(g) + Cl(g) ΔH =
Given that the ionization energy of F2- is 290. kJ/mol, do the following. a. Calculate the bond energy of F2-. You will need to look up the bond energy of F2 and ionization energy of F2. b. Explain
Bond energy has been defined in the text as the amount of energy required to break a chemical bond, so we have come to think of the addition of energy as breaking bonds. However, in some cases the
a. A flask containing gaseous N2 is irradiated with 25-nm light. Using the following information, indicate what species can form in this flask during irradiation. N2(g) → 2N(g) ΔH = 941 kJ/
Use the MO model to determine which of the following has the smallest ionization energy: N2, O2, N22-, N2-, O2+. Explain your answer.
Cholesterol (C27H46O) has the following structure:In such shorthand structures, each point where lines meet represents a carbon atom, and most H atoms are not shown. Draw the complete structure,
Arrange the following from lowest to highest ionization energy: O, O2, O2-, O2+. Explain your answer.
a. On the basis of electronegativities, would you expect the carbon atom or the oxygen atom to form bonds to metals?b. Assign formal charges to the atoms in CO. Which atom would you expect to bond to
Use the MO model to explain the bonding in BeH2. When constructing the MO energy-level diagram, assume that the Be 1s electrons are not involved in bond formation.
In Exercise 65 in Chapter 13, the Lewis structures for benzene (C6H6) were drawn. Using one of the Lewis structures, estimate ΔH°f for C6H6(g) using bond energies and given the standard enthalpy of
For each chemical formula below, an NMR spectrum is described, including relative overall areas (intensities) for the various signals given in parentheses. Draw the structure of a compound having the
Structural isomers are compounds that have the same chemical formula but the atoms are bonded together differently giving different compounds. Consider the two structural isomers having the formula
The sp2 hybrid atomic orbitals have the following general form:where Ï†s, Ï†px, and Ï†py represent orthonormal (normalized and orthogonalized) atomic orbitals. Calculate
What is a hydrocarbon? What is the difference between a saturated hydrocarbon and an unsaturated hydrocarbon? Distinguish between normal and branched hydrocarbons.
In the shorthand notation for cyclic alkanes, the hydrogens are usually omitted. How do you determine the number of hydrogens bonded to each carbon in a ring structure?
What are aromatic hydrocarbons? Give a detailed description of the bonding in benzene. The π electrons in benzene are delocalized, whereas the π electrons in simple alkenes and alkynes are
Draw all the structural isomers for C8H18 that have the following root name (longest carbon chain). Name the structural isomers. a. Heptane b. Hexane c. Pentane d. Butane
A general rule for a group of hydrocarbon isomers is that as the amount of branching increases, the boiling point decreases. Explain why this would be true.
Name the five structural isomers of C6H14
Draw the structural formula for each of the following. a. 3-isobutylhexane b. 2,2,4-trimethylpentane, also called isooctane. This substance is the reference (100 level) for octane ratings. c.
Draw the structure for 4-ethyl-2,3-diisopropylpentane. This name is incorrect. Give the correct systematic name.
Name each of the following.a.b. c. d.
Name each of the following cyclic alkanes, and indicate the formula of the compound.a.b. c.
Name each of the following alkenes or alkynes.a. CH2 = CH-CH2-CH3b.c. d. e. f. g.
Give the structure for each of the following. a. 3-hexene b. 2,4-heptadiene c. 2-methyl-3-octene d. 4-methyl-1 -pentyne
Name each of rhe following.a.b. CH3, CH2, CH2CCI3 c. d. CH2FCH2F e. f. g. h.
Distinguish between isomerism and resonance. Distin-guish between structural and geometric isomerism.
A confused student was doing an isomer problem and listed the following six names as different structural iso-mers of C7H16. a. 1-sec-butylpropane b. 4-methylhexane c. 2-ethylpentane d.
There is only one compound that is named 1, 2-dichloro-ethane, but there are two distinct compounds that can be named 1,2-dichloroethene. Why?
Which of the compounds in Exercise 13 exhibit cis-trans isomerism?

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