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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
Draw condensed formulas showing the multiple bonds, charges, and lone electron pairs (if any) for each molecule in the following pairs of constitutional isomers. (First make sure that you can draw a
Two resonance forms can be written for a bond between trivalent boron and an atom with a lone pair of electrons, (a) Formulate them for (i) (CH3)2BN(CH3)2; (ii) (CH3)2BOCH3; (iii) (CH3)2BF. (b) Using
The unusual molecule [2.2.2] propel-lane is pictured in the margin. On the basis of the given structural parameters, what hybridization scheme best describes the carbons marked by asterisks? (Make a
(a) On the basis of the information in Problem 38, give the likely hybridization of the orbital that contains the unshared pair of electrons (responsible for the negative charge) in each of the
A number of substances containing positively polarized carbon atoms have been labeled as "cancer suspect agents" (i.e., suspected carcinogens or cancer-inducing compounds). It has been suggested that
Certain compounds, such as the one pictured below, show strong biological activity against cell types characteristic of prostate cancer. In this structure, locate an example of each of the following
Consider the following reaction:(a) Draw these condensed formulas as Lew is dot structures. Label the geometry and hybridization of the bold carbons in compounds A and B. Did the hybridization change
A certain organic compound was found on combustion analysis to contain 84% carbon and \6c/c hydrogen (C = 12.0, H = 1.00). A molecular formula for the compound could be (a) CH4O (b) C6H14O2 (c)
The compoundhas a formal charge of (a) -1 on N (b) +2 on N (c) -1 on Al (d) +1 on Br (e) None of the above
The arrow in the structure in the margin points to a bond that is formed by (a) Overlap of an s orbital on H and an sp2 orbital on C (b) Overlap of an s orbital on H and an sp orbital on C (c)
Which compound has bond angles nearest to 120°? (a) O = C = S (b) CHI3 (c) H2C = O (d) H-C=C-H (e) CH4
The pair of structures that are resonance hybrids is(a)(b) (c) (d)
Draw a Lewis structure for each of the following molecules and assign charges where appropriate. The order in which the atoms are connected is given in parentheses. (a) C1F (b) BrCN (c)
The hydrocarbon propene (CH3-CH=CH2) can react in two different ways with bromine (Chapters 12 and 14).(i)(ii) (a) Using the bond strengths (kcal mol-1) given in the margin, calculate
(i) Determine whether each species in the following equations is acting as a Bronsted acid or base, and label it. (ii) Indicate whether the equilibrium lies to the left or to the right, (iii)
Use curved arrows to show electron movement in each acid-base reaction in Problem 27.
Identify each of the following species as either a Lewis acid or a Lewis base, and write an equation illustrating a Lewis acid-base reaction for each one. Use curved arrows to depict electron-pair
For each example in Table 2-3, identify all polarized covalent bonds and label the appropriate atoms with partial positive or negative charges. (Do not consider carbon-hydrogen bonds.)
Characterize each of the following atoms as being either nucleophilic or electrophilic. (a) Iodide ion, I- (b) Hydrogen ion, H+ (c) Carbon in methyl cation, +CH3 (d) Sulfur in hydrogen sulfide.
Circle and identify by name each functional group in the compounds pictured.(a)(b) (c) (d) (e) (f) (g) (h) (i) (j)
On the basis of electrostatics (Coulomb attraction), predict which atom in each of the following organic molecules is likely to react with the indicated reagent. Write "no reaction" if none seems
Use curved arrows to show the electron movement in each reaction in Problem 33.
Name the following molecules according to the IUPAC system of nomenclature.(a)(b) (c) (d) (e) CH3CH(CH3)CH(CH3)CH(CH3)CH(CH3)2 (f)
Convert the following names into the corresponding molecular structures. After doing so, check to see if the name of each molecule as given here is in accord with the IUPAC system of nomenclature. If
Draw the structures that correspond to the following names. Correct any names that are not in accord with the rules of systematic nomenclature. (a) 4-Chloro-5-methylhexane (b)
Draw and name all possible isomers of C7HI6 (isomeric heptanes).
Identify the primary, secondary, and tertiary carbon atoms and the hydrogen atoms in each of the following molecules: (a) Ethane; (b) Pentane; (c) 2-methylbutane; (d)
Identify each of the following alkyl groups as being primary, secondary, or tertiary, and give it a systematic IUPAC name.(a)(b) (c) (d) (e) (f)
Rank the following molecules in order of increasing boiling point (without looking up the real values!): (a) 3-methylheptane; (b) Octane; (c) 2,4-dimethylhexane; (d) 2,2,4-trimethylpentane.
Using Newman projections, draw each of the following molecules in its most stable conformation with respect to the bond indicated: (a) 2-methylbutane, C2-C3 bond; (b) 2,2-dimethylbutane, C2-C3
Based on the energy differences for the various conformations of ethane, propane, and butane in Figures 2-10, 2-11, and 2-13, determine the following: (a) The energy associated with a single
At room temperature, 2-methylbutane exists primarily as two alternating conformations of rotation about the C2-C3 bond. About 90% of the molecules exist in the more favorable conformation and 10% in
For each of the following naturally occurring compounds, identify the compound class(es) to which it belongs, and circle all functional groups.
Give IUPAC names for all alkyl groups marked by dashed lines in each of the following biologically important compounds. Identify each group as a primary, secondary, or tertiary alkyl substituent.
Using the Arrhenius equation, calculate the effect on k of increases in temperature of 10, 30, and 50 degrees (Celsius) for the following activation energies. Use 300 K (approximately room
The Arrhenius equation can be reformulated in a way that permits the experimental determination of activation energies. For this purpose, we take the natural logarithm of both sides and convert into
Reexamine your answers to Problem 33. Rewrite each one in the form of a complete equation describing a Lewis acid-base process, showing the product and using curved arrows to depict electron-pair
The equation relating △Go to K contains a temperature term. Refer to your answer to Problem 44 (a) to calculate the answers to the questions that follow. You will need to know that △So for the
Consider the difference in the rate between the following two second-order substitution reactions.Reaction 1: The reaction of bromoethane and iodide ion to produce iodoethane and bromide ion is
The compound 2-methylbutane has (a) No secondary H's (b) No tertiary H's (c) No primary H's (d) Twice as many secondary H's as tertiary H's (e) Twice as many primary H's as secondary H's
The energy profile diagram represents(a) An endothermic reaction(b) An exothermic reaction(c) A fast reaction(d) A termolecular reaction
In 4-( l-methylethyl)heptane. any H-C-C angle has the value (a) 120° (b) 109.5° (c) 180° (d) 90° (e) 360°
The structural representation shown in the margin is a Newman projection of the conformer of butane that is (a) Gauche eclipsed (b) Anti gauche (c) Anti staggered (d) Anti
Genipin (margin) is a Chinese herbal remedy that is effective against diabetes. To which of the compound classes below does genipin not belong? (a) Alcohol (b) Alkene (c) Ester (d) Ether (e)
Label the primary, secondary, and tertiary hydrogens in each of the following compounds.(a) CH3CH2CH2CH3(b) CH3CH2CH2CH2CH3(c)(d)
Within each of the following sets of alkyl radicals, name each radical; identify each as either primary, secondary, or tertiary; rank in order of decreasing stability; and sketch an orbital picture
Write as many products as you can think of that might result from the pyrolytic cracking of propane. Assume that the only initial process is C-C bond cleavage.
Answer the question posed in Problem 17 for (a) butane and (b) 2-methylpropane. Use the data in Table 3-2 to determine the bond most likely to cleave homolytically, and use that bond cleavage as your
Calculate ∆Ho values for the following reactions. (a) H2 + F2 → 2 HF; (b) H2 + Cl2 → 2 HC1; (c) H2 + Br2 → 2 HBr; (d) H2 + I2 → 2 HI; (e) (CH3)3CH + F2 → (CH3)3CF + HF; (f) (CH3)3CH + Cl2
For each compound in Problem 15, determine how many constitutional isomers can form upon monohalogenation.Problem 15(a) CH3CH2CH2CH3(b) CH3CH2CH2CH2CH3(c)(d)
(a) Using the information given in Sections 3-6 and 3-7, write the products of the radical monochlorination of (i) Pentane and (ii) 3-methylpentane. (b) For each, estimate the ratio of the isomeric
Write in full the mechanism for monobromination of methane. Be sure to include initiation, propagation, and termination steps.
Sketch potential-energy/reaction-coordinate diagrams for the two propagation steps of the mono-bromination of methane (Problem 22).
Write a mechanism for the radical bromination of the hydrocarbon benzene, C6H6 (for structure, see Section 2-3). Use propagation steps similar to those in the halogenation of alkanes, as presented in
Sketch potential-energy/reaction-coordinate diagrams for the two propagation steps of the mono-bromination of benzene (Problem 24). Problem 24 Write a mechanism for the radical bromination of the
Identify each of the diagrams you drew in Problem 25 as showing an early or a late transition state.
Write the major organic product(s), if any, of each of the following reactions.(a)(b)(c)(d)(e)
Calculate product ratios in each of the reactions in Problem 27. Use relative reactivity data for F2 and Cl2 at 25°C and for Br2 at 150°C (Table 3-6).Problem 27(a)(b) (c) (d) (e)
Which, if any, of the reactions in Problem 27 give the major product with reasonable selectivity (i.e., are useful "synthetic methods")?Problem 27(a)(b) (c) (d) (e)
(a) What would be the major organic product of monobromination of pentane at I25°C?(b) Draw Newman projections of all possible staggered conformations arising from rotation about the C2-C3 bond for
(a) Sketch a potential energy/reaction coordinate graph showing the two propagation steps for the monobromination of pentane to give the major product (Problem 30). Use DH° information from this
At room temperature, 1,2-dibromoethane exists as an equilibrium mixture in which 89% of the molecules are in an anti conformation and 11% are gauche. The comparable ratio for butane under the same
Sulfuryl chloride (SO2Cl2, see structure) is a liquid reagent that may be used for chlorinations of alkanes as a substitute for gaseous elemental chlorine. Propose a mechanism for chlorination of CH4
Use the Arrhenius equation (Section 2-1) to estimate the ratio of the rate constants k for the reactions of a C-H bond in methane with a chlorine atom and with a bromine atom at 25°C. Assume that
When an alkane with different types of C-H bonds, such as propane, reacts with an equimolar mixture of Br2 and Cl2, the selectivity in the formation of the brominated products is much worse than that
Bromination of 1-bromopropane gives the following results:Calculate the relative reactivities of the hydrogens on each of the three carbons toward bromine atoms. Compare these results with those from
A hypothetical alternative mechanism for the halogenation of methane has the following propagation steps. (i) X∙ + CH4 → CH3X + H∙ (ii) H∙ + X2 → HX + X∙ (a) Using DH° values from
The addition of certain materials called radical inhibitors to halogenation reactions causes the reactions to come to a virtually complete stop. An example is the inhibition by I2 of the chlorination
Two simple organic molecules that have been used as fuel additives are methanol (CH3OH) and 2-methoxy-2-methylpropane [tert-butyl methyl ether, (CH3)3COCH3]. The ∆H°comb values for these compounds
Figure 3-9 compares the reactions of CI∙ with the primary and secondary hydrogens of propane. (a) Draw a similar diagram comparing the reactions of Br∙ with the primary and secondary hydrogens of
Two of the propagation steps in the Cl∙/O3 system consume ozone and oxygen atoms (which are necessary for the production of ozone), respectively (Section 3-9). CI + O3 → CIO + O2 CIO + O → CI +
(a) Provide an IUPAC name for each of the isomers that you drew in Exercise 2-16 (a). (b) For each isomer that you drew and named here, give all the free radical monochlorination and monobromination
The reaction CH4 + Cl2 → CH3C1 + HCl is an example of (a) Neutralization (b) An acidic reaction (c) An isomerization (d) An ionic reaction (e) A radical chain reaction
The sum of all the digits that appear in the (IUPAC) name for this compound is which of the following?(a) Five(b) Six(c) Seven(d) Eight(e) Nine
In a competition reaction, equimolar amounts of the four alkanes shown were allowed to react with a limited amount of Cl2 at 300°C. Which one of these alkanes would be depleted most from the
The reaction of CH4 with Cl2 to yield CH3C1 and HCI is well known. On the basis of the values in the short table below, the enthalpy H° (kcal mol-1) of this reaction is(a) +135(b)
Write as many structures as you can that have the formula C5H10 and contain one ring. Name them.
Write as many structures as you can that have the formula C6H12 and contain one ring. Name them.
Name the following molecules according to the IUPAC nomenclature system.(a)(b) (c) (d) (e) (f)
Draw structural representations of each of the following molecules. Give a systematic name for any compound whose name is not in accord with IUPAC nomenclature: (a) isobutylcyclopentane; (b)
Draw structural representations of each of the following molecules: (a) trans-1-chloro-2-ethylcyclopropane; (b) cis-1-bromo-2-chlorocyclopentane; (c) 2-chloro-1,1-diethylcyclopropane; (d)
The kinetic data for the radical chain chlorination of several cycloalkanes (see the adjoining table) illustrate that the C-H bonds of cyclopropane and, to a lesser extent, cyclobutane are somewhat
Write out a mechanism for the radical monobromination of cyclohexane, showing initiation, propagation, and termination steps. Draw the product in its most stable conformation.
Use the data in Tables 3-2 and 4-2 to estimate the DH° value for a C-C bond in (a) cyclopropane: (b) cyclobutane: (c) cyclopentane; and (d) cyclohexane.
Draw each of the following substituted cylobutanes in its two intervonverting "puckered" conformations (Figure 4-3). When the two conformations differ in energy, identify the more stable shape and
For each of the following cyclohexane derivatives, indicate (i) whether the molecule is a cis or trans isomer and (ii) whether it is in its most stable conformation. If your answer to (ii) is no,
Using the data in Table 4-3, calculate the G° for ring flip to the other conformation of the molecules depicted in Problem 30. Make sure that the sign (i.e., positive or negative) of
Draw the most stable conformation for each of the following substituted cyclohexanes; then, in each case, flip the ring and redraw the molecule in the higher energy chair conformation:(a)
For each molecule in Problem 32, estimate the energy difference between the most stable and next best conformation. Calculate the approximate ratio of the two at 300 K.Problem 32:(a) cyclohexanol;(b)
Sketch a potential-energy diagram (similar to mat in Figure 4-9) for methylcyclohexane showing the two possible chair conformations at the left and right ends of the reaction coordinate for
Draw all the possible all-chair conformers of cyclohexylcyclohexane.
What is the most stable of the four boat conformations of methylcyclohexane, and why?
The most stable conformation of trans-1,3-bis(1,1-dimethylethyl(cyclohexane is not a chair. What conformation would you predict for this molecule? Explain.
The bicyclic hydrocarbon formed by the fusion of a cyclohexane ring with a cyclopentane ring is known as hexahydroindane (in margin). Using the drawings of trans- and cis-decalin for reference
On viewing the drawings of cis- and trans-decalin in Figure 4-13, which do you think is the more stable isomer? Estimate the energy difference between the two isomers.
Several tricyclic compounds exist in nature with a cyclopropane ring fused to a cis-decalin structure, as shown in the molecule tricyclo[5.4.01.3.01.7]undecane (margin). In various countries, some of
The naturally occurring sugar glucose (Chapter 24) exists in the two isomeric cyclic forms shown below. These are called α and β, respectively, and they are in equilibrium
Identify each of the following molecules as a monoterpene, a sesquiterpene, or a diterpene (all names are common).(a)(b) (c) (d) (e) (f) (g) (h)
Circle and identify by name each functional group in the structures pictured in Problem 42.Problem 42:(a)(b) (c) (d) (e) (f) (g) (h)
Find the 2-methyl-1.3-butadiene (isoprene) units in each of the naturally occurring organic molecules pictured in Problem 42.Problem 42:(a)(b) (c) (d) (e) (f) (g) (h)
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