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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Convert the following representation of ethane, C2H6. Into a conventional drawing that uses solid, wedged, and dashed lines to indicate tetrahedral geometry around each carbon (gray = c, ivory =H).
What are likely formulas for the following substances?(a) GeCl?(b) AlH?(c) CH? Cl2(d) SiF?(e) CH3NH?
Write line-bond structures for the following substances, showing all nonbonding electrons:(a) CHCl3, chloroform(b) H2S, hydrogen sulfide(c) CH3NH2, methylamine(d) CH3Li,methyllithium
Why can’t an organic molecule have the formula C2H7?
Draw a line-bond structure for propane, CH3CH2CH3. Predict the value of each bond angle, and indicate the overall shape of the molecule.
Convert the following molecule model of hexane, a component of gasoline, into a line-bond structure (gray = C, ivory =H).
Draw a line-bond structure for propane, CH3CH = CH2; indicate the hydribization of each carbon; and predict the value of each bond angle.
Draw a line-bond structure for 1, 3-butadiene, H2C = CH – CH = CH2; indicate the hydribization of each carbon; and predict the value of each bond angle.
Following is a molecule model of aspirin (acetylsalicylic acid). Identify the hydribization of each carbon atom in aspirin, and tell which atoms have lone pairs of electrons (gray = c. red = O, ivory
Draw a line-bond structure for the propyne, CH3C ≡ CH; indicate the hydribization of each carbon; and predict a value for each bond angle.
Identify all nonbonding lone pairs of electron in the following molecules, and tell what geometry you expect for each pf the indicated atoms. (a) The oxygen atom in the dimethyl ether, CH3 ? O ?
Tell how much hydrogen is bonded to each carbon in the following compounds, and give the molecular formula of each substance:
Propose skeletal structures for compounds that satisfy the following molecular formulas. There is more than one possibility in each case.(a) C5H12(b) C2H7N(c) C3H6O(d) C4H9Cl
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
Convert each of the following molecular models into skeletal structure, and give the formula of each. Only the connections between atoms are shown; multiple bonds are not indicated (gray = C, red ?
The following model is representation of critic acid, the key substance in the so-called citric acid cycle by which food molecules is metabolized in the body. Only the connection between atoms is
The following model is a representation of acetaminophen, a pain reliever sold in drugstores as Tylenol. Identify the hydribization of each carbon atom in acetaminophen, and tell which atoms have
The following model is a representation of asparatame, C14H18N2O5, known commercially as NutraSweet. Only the connection between atoms is shown; multiple bonds are not indicated. Complete the
How many valence electrons does the 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) NH? OH(b) A1C1?(c) CF2C1?(d) CH? O
Draw an electron-dot structure for Acetonitrile, C2H3N, 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
What is the hydribization of each carbon atom in acetonitrile (Problem 1.25)?
Draw a line-bond structure for vinyl chloride, C2H3C1, the starting material from which PVC [poly (vinyl chloride)] plastic is made.
Fill in any nonbonding valence electrons that are missing from the followingstructures:
Convert the following line-bond structures into molecularformulas:
Convert the following molecular formulas into line-bond structures that are sonsistent with valence rules:(a) C3H8(b) CH5N(c) C2H6O (2 possibilities)(d) C3H7Br (2 possibilities)(e) C2H4O (3
What kind of hybridization do you expect for each carbon atom in the followingmolecules?
What is the shape of benzene, and what hydribization do you expect for eachcarbon?
What bonds angles do you expect for each of the following, and what kind of hydribization do you expect for the central atom ineach?
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 ofeach:
Propose structures for molecules that meet the following descriptions:(a) Contains two sp2-hybridized carbons and two sp3-hybrized carbons(b) Contains only four carbons, all of which are
Why can’t molecules with the following formulas exist?(a) CH5(b) C2H6N(c) C3H5Br2
Draw a three-dimensional representation of the oxygen-bearing carbons atom in ethanol, CH3CH2OH, using the standard convention of solid, wedged, and dashed lines.
Oxaloacetic acid, an important intermediate in food metabolism, has the formula C4H4O5 and contains three C = O bonds and two O ─ H bonds. Propose two possible structures.
Draw structures for the following molecules(a) Acrylonitrile, C3H3N, which contains a carbon-carbon double bond and a carbon-nitrogen triple bond(b) Ethyl methyl ether, C3H8O, which contains an
Potassium methoxide, KOCH3, contains both covalent and ionic bonds. Which do you think is which?
What kind of hydribization do you expect for each carbon atom in the followingmolecules?
Pyridoxal phosphate, a close relative of vitamin B6, is involved in a large number of metabolic reactions. Tell the hydribization, and predict the bond angles for each non-terminalatom.
Why do you suppose no one has ever been able to make cyclopentyne as a stable molecule?
What is wrong with following sentences? “The π bonding molecular orbital in ethylene results from sideways overlap of two p atomic orbitals.”
Allene, H2C = C = CH2, is somewhat unusual in that it has two adjacent double bonds. Draw a picture showing the orbital’s involved in the σ and π bonds of allene. Is the central atom sp2- or
Allene (see problem 1.46) is related structurally to carbon dioxide, CO2. Draw a picture showing the orbital’s involved in the σ and π bonds CO2, and identify the likely hybridization of carbon.
Complete the electron-dot structure of caffeine, showing all lone-pair electrons, and identify the hybridization of the indicatedatoms.
Almost all 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 do
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 NH3? (b) How many
Divalent carbon species called carbenes care capable of fleeting existence. For example, methylene: CH2, is the simplest carbene. The two unshared electrons in methylene can be either spin-paired in
There are two different substances with the formula C4H10. Draw both, and tell how they differ.
There are two different substances with the formula C3H6. Draw both, and tell how they differ.
There are two different substances with the formula C2H6O. Draw both, and tell how they differ.
There are two different substances that contain a carbon-carbon double bond and have the formula C4H8. Draw them, and tell how they differ.
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
Which element in each of the following pairs is more electronegative?(a) Li or H(b) B or Br(c) C1 or I(d) C or h
Use the δ + /δ – convention to show the direction of expected polarity for each of the following bonds indicated.(a) H3C ─ C1(b) H3C ─ NH2(c) H2N ─ H(d) H3C ─ SH(e) H3C ─ MgBr(f) H3C
Use the electro-negatively values shown in Figure to rank the following bonds from least polar to most molar: H3C ? Li, H3C ? K, H3C ? F, H3C ? MgBr, H3C ? OH.
Look at the following electrostatic potential map of chloromethane, and tell the direction of polarization of the C ? C1 bonds:
Ethylene glycol, HOCH2CH2OH, has zero dipole moment even though carbon-oxygen bonds are strongly polarized. Explain.
Make three-dimensional drawings of the following molecules, and predict whether each has a dipole moment. If you expect a dipole moment, show its direction.(a) H2C = CH2(b) CHC13(c) CH2C12(d) H2C =
Nitromethane has the structure indicated. Explain why it must have formal charges on N andO.
Calculate formal charges for the non-hydrogen atoms in the following molecules: (a) Diazomethane, (b) Acetonitrile oxide, (c) Methylisocyanide,
Organic phosphate groups occur commonly in biological molecules. Calculate formal charges on the four O atoms in the methyl phosphatedianion.
Draw the indicated number of resonance forms for each of the following species: (a) The methyl phosphate anion, CH3OPO32- (3) (b) The nitrate anion, NO3- (3) (c) The allyl cation, H2C = CH ? CH2+
Nitric acid (HNO3) reacts with ammonia (NH3) to yield ammonium nitrate. Write the reaction, and identify the acid, the base, the conjugate acid product, and the conjugate base product.
The amino acid phenylalanine has pKa = 1.83, and tryptophan has pKa = 2.83. Which is the strongeracid?
Amide ion, H2N─, is a stronger base then hydroxide ion, HO─. Which is the stronger acid, NH3 or H2O? Explain.
Will either of the following reactions take place as written, according to the data inTable?
Ammonia, NH3, has pKa = 36 and acetone has pKa 19. Will the following reaction takeplace?
What is the Ka of HCN is its pKa = 9.31?
Using curved arrows, show how the species in part (a) can acts as Lewis bases in their reactions with HC1, and show how the species in part (b) can acts as Lewis acids in their reaction with
Imidazole forms part of the structure of the amino acid histidine and can acts as both an acid and a base (a) Look at the electrostatic potential map of Imidazole, and identify the most acidic
Of the two vitamins A and C, and is hydrophilic and water-soluble while the other is hydrophobic and fat-soluble. Which iswhich?
Fill in the multiple bonds in the following model of naphthalene, C10H8 (gray = C, ivory =H). How many resonance structures does naphthalenehave?
The following model is a representation of ibuprofen, a common over-the-counter pain reliever. Indicate the positions of the multiple bonds, and draw a skeletal structure (gray = C, red = O, ivory
Cis-1, 2-Dichloroethylene and trans-dichloroethylene are isomers, compounds with the same formula but different chemical structures. Look at the following electrostatic potential maps, and tell
The following molecular models are representations of (a) Adenine and (b) Cytosine constituents of DNA. Indicate the positions of the multiple bonds and lone pairs for both, and draw skeletal
Tell the number of hydrogens bonded to each carbon atom in the following substances and give the molecular formula ofeach:
Identify the most electronegative element in each of the following molecules:(a) CH2FC1(b) FCH2CH2CH2Br(c) HOCH2CH2NH2(d) CH3OCH2Li
Use the electro negatively table (Figure) to predict which bond in each of the following sets is more polar, and indicate the direction of bond polarity for each compound. (a) H3C ? C1 OR C1 ? C1 (b)
Which of the following molecules has a dipole moment? Indicate the expected direction ofeach.
(a) The H ─ C1 bond length is 136 pm. What would the dipole moment of HC1 be if the molecule were 100% ionic, H+ C1-?(b) The actual; dipole moment HC1 is 1.08 D. What is the percent ionic character
Phosgene, C12C = O, has a smaller dipole moment then formaldehyde, H2C = O, even though it contains electronegative chlorine atoms in place of hydrogen. Explain
Fluoromethane (CH3F, μ = 1.81 D) has a smaller dipole moment than chloromethane (CH3C1, μ = 1.87 D) even though fluorine is more electronegative then chlorine. Explain
Methanethiol, CH2SH, has a substantial dipole moment (μ = 1.52) even though carbon and sulfur have identical electro negativities. Explain.
Calculate the formal charges on the atoms shown inred.
Which of the following pairs of structures represent resonanceforms?
Draw as many resonance structures as you can for the followingspecies:
Cyclobutadiene is a rectangular molecule with two shorter double bonds and two longer single bonds. Why do the following structures not represent resonance forms?
Alcohols can act either as weak acid or as weak bases, just as water can. Show the reaction of methanol, CH3OH, with a strong acid as HC1 and with a strong base such as NA+ -NH2.
The O ? H hydrogen in acetic acid is much more acidic than any of the C ? H hydrogens. Explain this result using resonance structures.
Write the products of the following acid-base reactions:(a) CH3OH + H2SO4 ↔?(b) CH3OH + NaNH2 ↔?(c) CH3NH3 + C1- +NAOH ↔?
Assign formal charger to the atoms in each of the followingmolecules:
Maleic acid has a dipole moment, but the closely related fumaric acid, a substance involved in the citric acid cycle by which food molecules are metabolized, does not.Explain
Rank the following substances in order of increasing acidity:
Which, if any, of the four substances in Problem 2.43 is a strong enough acid to react almost completely with NaOH? (The pKa of H2O is 15.74.)
The ammonium ion (NH4+, pKa = 9.25) has a lower pKa then the methyl-ammonium ion (CH3NH3+, pKa = 10.66). Which is the stronger base, ammonia (NH3) or methylamine (CH3NH2)? Explain
Is tert-butoxide anion a strong enough base to react with water? In other words, can a solution of potassium tert-butoxide be prepared in water? The pKa of tert-butyl alcohol is approximately18.
Predict the structure of the product formed in the reaction of the organic base pyridine with the organic acid acetic acid, and use curved arrows to indicate the direction of electronflow.
Calculate Ka values from the following pKa’s:(a) Acetone, pKa = 19.3(b) Formic acid, pKa = 3.75
Calculate pKa values from the following Ka’s:(a) Nitromethane, Ka = 5.0 x 10-11(b) Acrylic acid, Ka = 5.6 x 10-5

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