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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Use VSEPR theory to predict the geometry of each of the following molecules and ions: (a) H4 (b) BeF2 (c) (d) H2S (e) BH3 (f) CF4 (g) SiF4 (h)
Predict the bond angles of (a) F2C==CF2 (b) CH3Ci==CCH3 (c) HCi==N
Which of the following ions possess the electron configuration of a noble gas? (a) Na+ (b) Cl- (c) F+ (d) H- (e) Ca2+ (f) S2- (g) O2-
Write a Lewis structure for each of the following: (a) SOCl2 (b) POCl3 (c) PCl5 (d) HONO2 (HNO3)
Give the formal charge (if one exists) on each atom of the following:(a)(b) (c) (d)
Add any unshared electrons to give each element an octet in its valence shell in the formulas below and indicate any formal charges.All of the hydrogen atoms that are attached to heteroatoms have
Write a condensed structural formula for each compound given here.(a)(b) (c) (d)
What is the molecular formula for each of the compounds given in Exercise 1.33?(a)(b) (c) (d)
Consider each pair of structural formulas that follow and state whether the two formulas represent the same compound, whether they represent different compounds that are constitutional isomers of
Rewrite each of the following using bond-line formulas:(a)(b) (c) (CH3)3CCH2CH2CH2OH (d) (e) CH2==CHCH2CH2CH==CHCH3 (f)
Write bond-line formulas for all of the constitutional isomers with the molecular formula C4H8.
Write structural formulas for at least three constitutional isomers with the molecular formula CH3NO2. (In answering this question you should assign a formal charge to any atom that bears one.)
Write the resonance structure that would result from moving the electrons in the way indicated by the curved arrows.
Consider the following compounds and decide whether the bond in them would be ionic or covalent. (a) KCl (b) F2 (c) PH3 (d) CBr4
Show the curved arrows that would convert A into B.
For the following write all possible resonance structures. Be sure to include formal charges where appropriate.(a)(b) (c) (d) (e) (f) (g) (h) (i)
(a) Cyanic acid (H-O-C≡N) and isocyanic acid (H-N==C==O) differ in the positions of their electrons but their structures do not represent resonance structures. Explain. (b) Loss of a proton from
Consider a chemical species (either a molecule or an ion) in which a carbon atom forms three single bonds to three hydrogen atoms and in which the carbon atom possesses no other valence
Consider a chemical species like the one in the previous problem in which a carbon atom forms three single bonds to three hydrogen atoms, but in which the carbon atom possesses an unshared electron
Consider another chemical species like the ones in the previous problems in which a carbon atom forms three single bonds to three hydrogen atoms but in which the carbon atom possesses a single
Draw a three-dimensional orbital representation for each of the following molecules, indicate whether each bond in it is a s or p bond, and provide the hybridization for each non-hydrogen atom. (a)
Ozone (O3) is found in the upper atmosphere where it absorbs highly energetic ultraviolet (UV) radiation and thereby provides the surface of Earth with a protective screen. One possible resonance
Write resonance structures for the azide ion, N3-. Explain how these resonance structures account for the fact that both bonds of the azide ion have the same length.
Write structural formulas of the type indicated:(a) Bond-line formulas for seven constitutional isomers with the formula C4H10O;(b) Condensed structural formulas for two constitutional isomers with
Write the Lewis structure of (a) CH2Fl2 (difluoromethane) (b) CHCl3 (chloroform).
What is the relationship between the members of the following pairs? That is, are they constitutional isomers, the same, or something else (specify)?(a)(b) (c) (d) (e) (f)
Given the following sets of atoms, write bond-line formulas for all of the possible constitutionally isomeric compounds or ions that could be made from them. Show all unshared electron pairs and all
(a) Consider a carbon atom in its ground state. Would such an atom offer a satisfactory model for the carbon of methane? If not, why not?(b) Consider a carbon atom in the excited state:Excited state
Open computer molecular models for dimethyl ether, dimethylacetylene, and cis-1,2- ichloro-1,2-difluoroethene from the 3D Molecular Models section of the book's website. By interpreting the computer
Boron is a group IIIA element. Open the molecular model for boron trifluoride from the 3D Molecular Models section of the book's website. Near the boron atom, above and below the plane of the atoms
There are two contributing resonance structures for an anion called acetaldehyde enolate, whose condensed molecular formula is CH2CHO-. Draw the two resonance contributors and the resonance hybrid,
Write a Lewis structure for each of the following: (a) HF (b) F2 (c) CH3F (d) HNO2 (e) H2SO3 (f) BH4 (g) H3PO4 (h) H2CO3
Write bond-line structural formulas for (a) Two constitutionally isomeric primary alkyl bromides with the formula C4H9Br, (b) A secondary alkyl bromide, and (c) A tertiary alkyl bromide with the same
Although we shall discuss the naming of organic compounds later when we discuss the individual families in detail, one method of naming alkyl halides is so straightforward that it is worth describing
Write bond-line structural formulas for (a) Two primary alcohols, (b) A secondary alcohol, and (c) A tertiary alcohol-all having the molecular formula C4H10O.
One way of naming alcohols is to name the alkyl group that is attached to the -OH and add the word alcohol. Write bond-line formulas for (a) Propyl alcohol and (b) Isopropyl alcohol.
One way of naming ethers is to name the two alkyl groups attached to the oxygen atom in alphabetical order and add the word ether. If the two alkyl groups are the same, we use the prefix di-, for
Eugenol is the main constituent of the natural oil from cloves. Circle and label all of the functional groups in eugenol.Eugenol (found in cloves)
One way of naming amines is to name in alphabetical order the alkyl groups attached to the nitrogen atom, using the prefixes di- and tri- if the groups are the same. An example is isopropylamine,
Amines are like ammonia in being weak bases. They do this by using their unshared electron pair to accept a proton. (a) Show the reaction that would take place between trimethyl amine and HCl. (b)
Write the resonance structure for carvone that results from moving the electrons as indicated. Include all formal charges.
Write (+ and (- by the appropriate atoms and draw a dipole moment vector for any of the following molecules that are polar: (a) HF (b) IBr (c) Br2 (d) F2
Write bond-line formulas for (a) Four aldehydes and (b) Three ketones that have the formula C5H10O.
Write bond-line formulas for four carboxylic acids with the formula C5H10O2.
Write bond-line formulas for three esters with the formula C5H10O2.
Write another resonance structure for ethyl acetate. Include formal charges.
Write another resonance structure for acetamide.
The compounds in each part below have the same (or similar) molecular weights. Which compound in each part would you expect to have the higher boiling point? Explain your answers.(a)(b)(c)
Arrange the following compounds in order of increasing boiling point. Explain your answer in terms of the intermolecular forces in each compound.(a)(b) (c) (d)
Use arguments based on resonance and electronegativity effects to explain the trend in carbonyl IR stretching frequencies from higher frequency for esters and carboxylic acids to lower frequencies
Classify each of the following compounds as an alkane, alkene, alkyne, alcohol, aldehyde, amine, and so forth.(a)(b) CH3-C‰¡CH (c) (d) (e) (f)
Boron trifluoride (BF3) has no dipole moment (μ = 0 D). Explain how this observation confirms the geometry of BF3 predicted by VSEPR theory.
Identify all of the functional groups in each of the following compounds:(a)(b) (c) (d) (e) (f) (g)
There are four alkyl bromides with the formula C4H9Br. Write their structural formulas and classify each as to whether it is a primary, secondary, or tertiary alkyl bromide.
There are seven isomeric compounds with the formula C4H10O. Write their structures and classify each compound according to its functional group.
Classify the following alcohols as primary, secondary, or tertiary:(a)(b) (c) (d)
Classify the following amines as primary, secondary, or tertiary:(a)(b) (c) (d) (e) (f)
Write structural formulas for each of the following: (a) Three ethers with the formula C4H10O. (b) Three primary alcohols with the formula C4H8O. (c) A secondary alcohol with the formula C3H6O. (d) A
Identify all of the functional groups in Crixivan, an important drug in the treatment of AIDS.Crixivan (an HIV protease inhibitor)
Identify all of the functional groups in the following molecule.
(a) Indicate the hydrophobic and hydrophilic parts of vitamin A and comment on whether you would expect it to be soluble in water.(b) Do the same for vitamin B3 (also called niacin).
Hydrogen fluoride has a dipole moment of 1.83 D; its boiling point is 19.34oC. Ethyl fluoride (CH3CH2F) has an almost identical dipole moment and has a larger molecular weight, yet its boiling point
Tetrachloroethene (CCl2==CCl2) does not have a dipole moment. Explain this fact on the basis of the shape of CCl2==CCl2.
Why does one expect the cis isomer of an alkene to have a higher boiling point than the trans isomer?
Cetylethyldimethylammonium bromide is the common name fora compound with antiseptic properties. Predict its solubility behavior in water and in diethyl ether.
Write a three-dimensional formula for each of the following molecules using the wedge-dashed wedge-line formalism. If the molecule has a net dipole moment, indicate its direction with an arrow, →.
Consider each of the following molecules in turn: (a) Dimethyl ether, (CH3)2O; (b) Trimethylamine, (CH3)3N; (c) Trimethylboron, (CH3)3B; and (d) Dimethylberyllium, (CH3)2Be. Describe the
Analyze the statement: For a molecule to be polar, the presence of polar bonds is necessary, but it is not a sufficient requirement.
Which compound in each of the following pairs would have the higher boiling point? Explain your answers.(a)(b)(c)(d)(e)(f)(g)(h) Hexane, CH3(CH2)4CH3, or nonane, CH3(CH2)7CH3(i)
Predict the key IR absorption bands whose presence would allow each compound in pairs (a), (c), (d), (e), (g), and (i) from Problem 2.46 to be distinguished from each other.In problems
The IR spectrum of propanoic acid (Fig. 2.17) indicates that the absorption for the O-H stretch of the carboxylic acid functional group is due to a hydrogen-bonded form. Draw the structure of two
In infrared spectra, the carbonyl group is usually indicated by a single strong and sharp absorption. However, in the case of carboxylic acid anhydrides,two peaks are observed even though the two
Sulfur dioxide (SO2) has a dipole moment (μ = 1.63 D); on the other hand, carbon dioxide has no dipole moment (μ = 0 D). What do these facts indicate about the geometry of sulfur dioxide?
Write structural formulas for four compounds with the formula C3H6O and classify each according to its functional group. Predict IR absorption frequencies for the functional groups you have drawn.
There are four amides with the formula C3H7NO. (a) Write their structures. (b) One of these amides has a melting and a boiling point that are substantially lower than those of the other three. Which
Cyclic compounds of the general type shown here are called lactones. What functional group does a lactone contain?
Two constitutional isomers having molecular formula C4H6O are both symmetrical in structure. In their infrared spectra, neither isomer when in dilute solution in CCl4 (used because it is nonpolar)
When two substituents are on the same side of a ring skeleton, they are said to be cis, and when on opposite sides, trans (analogous to use of those terms with 1,2-disubstituted alkene isomers).
Examine the diagram showing an a-helical protein structure in Section 2.13E. Between what specific atoms and of what functional groups are the hydrogen bonds formed that give the molecule its helical
Using a three-dimensional formula, show the direction of the dipole moment of CH3OH. Write (+ and (- signs next to the appropriate atoms.
Trichloromethane (CHCl3, also called chloroform) has a larger dipole moment than CFCl3. Use three-dimensional structures and bond moments to explain this fact.
Indicate the direction of the important bond moments in each of the following compounds (neglect C-H bonds). You should also give the direction of the net dipole moment for the molecule. If there is
Write structural formulas for all of the alkenes with (a) The formula C2H2Br2 and (b) The formula C2Br2Cl2. In each instance designate compounds that are cis-trans isomers of each other. Predict the
Write structures for all compounds with molecular formula C4H6O that would not be expected to exhibit infrared absorption in the 3200-3550-cm-1 and 1620-1780-cm-1 regions.
Add curved arrows to the following reactions to indicate the flow of electrons for all of the bond-forming and bond-breaking steps.(a)(b)
Most carboxylic acids dissolve in aqueous solutions of sodium bicarbonate (NaHCO3) because, as carboxylate salts, they are more polar. Write curved arrows showing the reaction between a generic
State whether you would expect the entropy change, ∆So, to be positive, negative, or approximately zero for each of the following reactions. (Assume the reactions take place in the gas phase.) (a)
(a) What is the value of ∆Go for a reaction where Keq = 1? (b) Where Keq = 10? (The change in ∆Go required to produce a 10-fold increase in the equilibrium constant is a useful term to
Draw contributing resonance structures and a hybrid resonance structure that explain two related facts: the carbon-oxygen bond distances in the acetate ion are the same, and the oxygen's of the
Which would you expect to be the stronger acid? Explain your reasoning in each instance. (a) CH2ClCO2H or CHCl2CO2H (b) CCl3CO2H or CHCl2CO2H (c) CH2FCO2H or CH2BrCO2H (d) CH2FCO2H or CH2FCH2CO2H
It is a general rule that any organic compound containing oxygen, nitrogen, or a multiple bond will dissolve in concentrated sulfuric acid. Explain the basis of this rule in terms of acid-base
Write equations for the acid-base reaction that would occur when each of the following compounds or solutions are mixed. In each case label the stronger acid and stronger base, and the weaker acid
Complete the following acid-base reactions: (a) HC≡CH + NaH
What is the conjugate base of each of the following acids? (a) NH3 (b) H2O (c) H2 (d) HCi≡CH (e) CH3OH (f) H3O+
Write equations showing the Lewis acid-base reaction that takes place when: (a) Methanol (CH3OH) reacts with BF3. (b) Chloromethane (CH3Cl) reacts with AlCl3. (c) Dimethyl ether (CH3OCH3) reacts with
What is the conjugate acid of each of the following bases? (a) HSO4- (b) H2O (c) CH3NH2 (d) -NH2 (e) CH3CH2 (f) CH3CO2-
Designate the Lewis acid and Lewis base in each of the following reactions:(a)(b) (c)
Rewrite each of the following reactions using curved arrows and show all nonbonding electron pairs:(a)(b) (c)
Follow the curved arrows and write the products.(a)(b) (c) (d)
Write an equation, using the curved-arrow notation, for the acid-base reaction that will take place when each of the following are mixed. If no appreciable acid-base reaction takes place, because the

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