Predict the major product from each of the following reactions. (a) (b) (c) (d) (e) (f) (g) (h) (i) CH NH2, cat. HA N-H, cat. HA NH2 cat. HA PPha (1) HS SH (2) Raney Ni, H2 0 CH2PPha (excess) O. O...
Provide the reagents necessary for the following synthesis. OH HO Start with and make
Provide reagents that would accomplish each of the following syntheses. Begin by writing a retrosynthetic analysis. (a) (b) HO HO or OH
Provide a mechanism for the following reaction. (1) NaOEt (2) H3o 3 + 3
Provide the major organic product from each of the following reactions. (a) (b) (c) (d) (e) NH2 (1) cat. HA (2) NaBH3CN Br (1) NaCN (2)LiAlH4- (3) H20 Br )NaN3 (2) LiAIH4 (3) H2o (1) NH20H, cat. HA...
Draw the curved-arrow mechanism for the reaction in Eq. 4,29 that accounts for the formation of both products.
How many stereoisomers are there of 3,4-dimethyl-2- hexene? (a) Show all of the carbon stereocenters in the structure of this compound. (b) Show all of the asymmetric carbons in the structure of this...
A chemist, Ilov Boronin, carried out a reaction of frans-2-pentene with BH3 in THF followed by treatment with H2O2/-OH. Two products were separated and isolated. Desperate to know their structures,...
The following compound is not aromatic even though it has 4n + 2 electrons in a continuous cyclic array. Explain why this compound is not aromatic.
A chemist finds that the addition of (+)-epinephrine to the catalytic reduction of butan-2-one (Figure 5-16) gives a product that is slightly optically active, with a specific rotation of +0.45o...
For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2). (a) 2-chloro-2-methylbutane + CH3COOH (b)...
Classify each compound as an alkyl halide, a vinyl halide, or an aryl halide. (a) CH3CHCFCH3 (b) (CH3)3CBr (c) CH3CCl3 (d) (e) (f) Br bromocyclohexane Br l-bromocyclohexene CI CI CI Cl CI a PCB...
Propose a mechanism involving a hydride shift or an alkyl shift for each solvolysis reaction. Explain how each rearrangement forms a more stable intermediate. (a) (b) (c) (d) CH I CH OCH CH,O CH CH...
Predict the major product of the following reaction, and give a mechanism to support your prediction. NBS, h CH,CH ethylbenzene
The reaction of an amine with an alkyl halide gives an ammonium salt. The rate of this SN2 reaction is sensitive to the polarity of the solvent. Draw an energy diagram for this reaction in a nonpolar...
Show how you would synthesize the following compounds from acetylene and any other needed reagents: (a) 6-phenylhex-1-en-4-yne (b) cis-1-phenylpent-2-ene (c) trans-1-phenylpent-2-ene (d) CHPh ...
Show how you would synthesize the following alcohols from appropriate alkenes. (a) (b) (c) (d) ,
The spectrum of trans-hex-2-enoic acid follows. (a) Assign peaks to show which protons give rise to which peaks in the spectrum. (b) Draw a tree to show the complex splitting of the vinyl proton...
Determine the number of different kinds of protons in each compound. (a) 1-chloropropane (b) 2-chloropropane (c) 2, 2-dimethylbutane (d) 2, 3-dimethylbutane (e) 1-bromo-4-methylbenzene (f)...
Predict the mononitration products of the following compounds. (a) o-nitrotoluene (b) m-chlorotoluene (c) o-bromobenzoic acid (d) p-methoxybenzoic acid (e) m-cresol (m-methylphenol) (f)...
When bromine is added to two beakers, one containing phenyl isopropyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while...
Give appropriate names for the following compounds: (a) (b) (c) (d) (e) (f) (g) (h) (i) (j) (k) (l) CH2 Ph-CO-CH CH CH NH C-Ph Ph-OC CH Ph-C-O-CH CN CH30-C CH3 C-N(CH CH32 CH;CH2
Predict the products of the following aldol condensations. Show the products both before and after dehydration. (a) (b) (c) (d) (e) (f) CH3 TOH CH CH2-C-H CH TOH Ph-C-CH+ OH
The strongly hydrophilic polymer shown below is used in soft contact lenses. (a) Suggest how you might synthesize this polymer from methacrylic acid and any other reagents you need. (b) What is it...
Draw the important resonance contributors for the benzenonium intermediate in the bromination of aniline, and explain why ortho, para substitution predominates. NH2 aniline
What chemical test will distinguish between the compounds in each of the following pairs? Indicate what is visually observed with each test. a. Phenol and anisole b. 1-butanol and methyl propyl ether...
Write a mechanism for the reaction shown in eq. 10.35. room C-OCH, +HCl (10.35) temp benzoyl chloride methyl benzoate
Devise a synthesis of CH2CH2NH2 from CH2Br
Excluding compounds that contain methyl or ethyl groups, write structural formulas for all the bicyclic isomers of (a) C5H8 and (b) C6H10.
Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of...
Using 1-bromobutane and any necessary organic or inorganic reagents, suggest efficient syntheses of each of the following alcohols: (a) 1-Pentanol (b) 2-Hexanol (c) 1-Phenyl-1-pentanol (d)...
Give the structure of the product derived by intramolecular aldol condensation of the keto aldehyde shown: O CHI KOH. H-0 CH CCH CCHOCHIoO CH3
In each of the following pairs of compounds, choose the one that has the greater enol content, and write the structure of its enol form: (a) (b) (c) (d) (e) (f) (CH)3CCH or (CH2CHCH CH CC H or...
Propose methods for preparing butanoic acid from each of the following: (a) 1-Butanol (b) Butanal (f (c) 1-Butene (d) 1-Propanol (e) 2-Propanol (f) Acetaldehyde (g) CH3CH2CH(CO2H)2
On standing in dilute aqueous acid, compound A is smoothly converted to mevalonolactone. Suggest a reasonable mechanism for this reaction. What other organic product is also formed? CH3 CH3 CHj ...
Propane (C3H8) burns in oxygen to produce carbon dioxide gas and water vapor. (a) Write a balanced equation for this reaction. (b) Calculate the number of liters of carbon dioxide measured at STP...
Calculate the pH of 1.00 L of the buffer 1.00 M CH3COONa/1.00 M CH3COOH before and after the addition of (a) 0.080 mol NaOH, (b) 0.12 mol HCl.
Calculate the equilibrium pressure of CO2 due to the decomposition of barium carbonate (BaCO3) at 25C.
Determine whether each of the following compounds is a cis isomer or a trans isomer a. b. c. d. e. f. Cl Br CH3 CH3 Br Br CH3 Cl CH3 CH3 CH
Draw curved arrows to show the flow of electrons responsible for the conversion of the reactants into the products: Br
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) C7H16...
Which compound will not exhibit optical activity? (Note that these are all Fischer projections.) (a) (b) (c) (d) COOCH, Cl COCH CHs COOCH HO COOH COOH OH HOH HO HO COOH COOH OH CI OH COOH
Formulate the potential product of each of the following reactions. As you did in Problem 44, write "no reaction" where appropriate. (Identify the expected leaving group in each of the substrates and...
In an attempt to make 1-chloro-l-cyclobutylpentane, the following reaction sequence was employed. The actual product isolated, however, was not the desired molecule but an isomer of it. Suggest a...
Set up a thermodynamic cycle for determining the enthalpy of hydration of Ca2+ ions using the following data: enthalpy of sublimation of Ca (s), + 178.2 k] mol-1, first and second ionization...
The volume of a certain liquid varies with temperature as V= V'{0.77 + 3.7 x 10 -4 (T/K) + 1.52 X 10 -6 (T/K) 2 }
(a) Could 25 g of argon gas in a vessel of volume 1.5 dm3 exert a pressure of 2.0 bar at 30C if it behaved as a perfect gas? If not, what pressure would it exert? (b) What pressure would it exert if...
Use thevirial theorem to obtain an expression for the relation between the mean kinetic and potential energies of an electron in a hydrogen atom?
Name the following compounds: a) c) H C CH3 b) d)
How would you synthesize the following substances starting frombenzene? ( C-CH2 .CH- (a) (c) H
The following reaction involves two successive intra molecular Michael reactions. Write both steps, and show theirmechanisms. Nat "OEt Ethanol
The following reaction involves an intra molecular aldol reaction followed by a ret ro aldol-like reaction. Write both steps, and show theirmechanisms. O2Et CO2Et Na* "OEt Ethanol
Section 2.3 describes the postulates of Daltons atomic theory. With some modifications, these postulates hold up very well regarding how we view elements, compounds, and chemical reactions today....
Thompson Corporation is planning to issue $ 100,000, five-year, 6 percent bonds. Interest is payable semi-annually each June 30 and December 31. All of the bonds will be sold on July 1, 2014; they...
What is the volume of 100.0 g of lead if lead has a density of 11.34 g/cm3?
From the elements position on the periodic table, predict the electron configuration of each atom. a. Cl b. K
Predict the type of solid exhibited by each substance. a. Co b. CO c. CaCO3
What are the individual ion concentrations and the total ion concentration in 1.04 M Al2(SO4)3?
Using concentration as a conversion factor, how many moles of solute are in 3.44 L of 0.753 M CaCl2?
If 25.0 g of C6H12O6 are dissolved in 100.0 g of H2O, what is the boiling point of this solution?
What volume of pool water is needed to generate 1.000 L of Cl2(g) at standard temperature and pressure if the pool contains 4.0 ppm HOCl and the water is slightly acidic? The chemical reaction is as...
Name this molecule. Br Br Br FC-C-C
Rate laws are not restricted to chemical systems; they are used to help describe many everyday events. For example, a rate law for tree growth might look something like this: Rate of growth = (soil...
Ethanolamine, HOC2H4NH2, is a viscous liquid with an ammonialike odor; it is used to remove hydrogen sulfide from natural gas. A 0.15 Maqueous solution of ethanolamine has a pH of 11.34. What is Kb...
Using values from Appendix C, calculate the standard enthalpy change for each of the following reactions: (a) 2 SO2(g) + O2(g) 2 SO3(g) (b) Mg(OH)2 (s) MgO (s) + H2O(I) (c) N2O4(g) + 4 H2(g) N2(g)...
(a) Cyanic acid (H-O-CN) 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...
Identify all of the functional groups in each of the following compounds: (a) (b) (c) (d) (e) (f) (g) Vitamin D3 HO OMe Aspartame O NH2 NH2 Amphetamine Me Cholesterol HO OCH2CH3 Demerol CH A...
Write a conformational structure for 1-bromo-3-chloro-5-fluorocyclohexane in which all the substituents are equatorial. Then write its structure after a ring flip.
Sketch curves similar to the one given in Fig. 4.8 showing the energy changes that arise from rotation about the C2-C3 bond of (a) 2,3-dimethylbutane and (b) 2,2,3,3-etramethylbutane. You need not...
Some of the molecules listed here have a chirality center; some do not. Write three-dimensional formulas for both enantiomers of those molecules that do have a chirality center. (a) 2-Fluoropropane...
When cis-1-bromo-4-tert-butylcyclohexane is treated with sodium ethoxide in ethanol, it reacts rapidly; the product is 4-tert-butylcyclohexene. Under the same conditions, trans-...
When (S)-2-bromopropanoic acid [(S)-CH3CHBrCO2H] reacts with concentrated sodium hydroxide, the product formed (after acidification) is (R)-2-hydroxypropanoic acid [(R)-CH3CHOHCO2H, commonly known as...
Synthesize each of the following compounds by routes that involve allylic bromination by NBS. Use starting materials having four carbons or fewer. Begin by writing a retrosynthetic analysis. (a) (b)...
Draw all of the stereoisomers that are possible for 1,2,3-cyclopentanetriol. Label their chirality centers and say which are enantiomers and which are diastereomers. (Some of the isomers contain a...
Predict the products of the following reactions. (a) (b) (1) EtMgBr (excess) (1) EMgBr (excess) HOEt 2) NH.CI, H2O
Provide a mechanism for the following reaction and explain why it occurs faster than nitration of benzene. NO2
Predict the major product (or products) that would be obtained when each of the following compounds is nitrated: (a) (b) (c) OH CF CN SO3H OCH3 NO2
What monobromination product (or products) would you expect to obtain when the following compounds undergo ring Bromination with Br2 and FeBr3? (a) (b) (c) N.
Starting with styrene, outline a synthesis of each of the following: (a) (b) (c) (d) (e) (f) (g) (h) (i) (j) (k) (l) (m) (n) Cl Cl CHs OH OH C&Hs OH OH C6H5 Br C6H5 caHs CeHs C6H5
Propose structures for compounds G-I: concd HNO heat 60-65 OH
The compound phenylbenzene (C6H5 -C6H5) is called biphenyl, and the ring carbons are numbered in the following manner: Use models to answer the following questions about substituted biphenyls. (a)...
Predict the major products formed when: (a) Toluene is sulfonated. (b) Benzoic acid is nitrated. (c) Nitrobenzene is brominated. (d) Isopropylbenzene reacts with acetyl chloride and AlCl3. If the...
Phenol reacts with acetic anhydride in the presence of sodium acetate to produce the ester phenyl acetate: The CH3COOi- group of phenyl acetate, like the -OH group of phenol (Practice Problem 15.8),...
(a) Show how you might use a cyclic acetal in carrying out the following transformation: (b) Why would a direct addition of methylmagnesium bromide to A fail to give B? OH
(a) Show how you might prepare lactic acid from acetaldehyde through a cyanohydrin intermediate. (b) What stereoisomeric form of lactic acid would you expect to obtain? OH CO2H
(a) Synthesize phenyl propyl ketone from benzene and any other needed reagents. (b) Give two methods for transforming phenyl propyl ketone into butylbenzene.
Write detailed mechanisms for each of the following reactions. (a) (b) (c) (d) H2SO4 (cat.) OH CH OH, H2SO, (cat.) H20, H2SO, (cat.) NH O H20, H SO, (cat.)
Show how benzaldehyde could be synthesized from each of the following: (a) Benzyl alcohol (b) Benzoic acid (c) Phenylethyne (d) Phenylethene (styrene) (e) C6H5CO2CH3 (f) C6H5C(N
Compounds A and D do not give positive Tollens' tests; however, compound C does. Give structures for A-D. HOCH CH2OH, HA Mg, Et20 (1) CH CHO CH3OH D (C,H1402)
Starting with benzyl bromide, show how you would synthesize each of the following: (a) (b) (c) (d)
Provide the reagents and indicated intermediates in each of the following syntheses. (a) (b) (c) (d) (e) (f) OH CI OH Br CN
Write a detailed mechanism for the following reaction. OH OH H2SO4 (cat), H2O HO OH
The reaction of an aldehyde or ketone with a Grignard reagent is a nucleophilic addition to the carbon-oxygen double bond. (a) What is the nucleophile? (b) The magnesium portion of the Grignard...
Indicate the reagents needed for each of the following syntheses. More than one step may be needed. (a) (b) HO OH OH
Starting with benzene or toluene, outline a synthesis of each of the following compounds using diazonium salts as intermediates. (You need not repeat syntheses carried out in earlier parts of this...
Predict the product of the following reactions. (a) (b) (c) (d) (e) (f) (g) (h) (i) HBr (excess), OH (1) NaH OH Br2 (excess) H20 H3C OH excess QH (1) NaH,Br (2) heat HNO3, H2SO4 NaNH2, NHa (1) NaOH...
All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly. (a) 2-methylethylpentane (b) 2-ethyl-3-methylpentane (c)...
The preceding example shows meso-1,2-dibromo-1,2-diphenylethane reacting with iodide ion to give trans-stilbene. Show how the other diastereomer of the starting material gives a different...
(a) Draw a detailed mechanism for the FeBr3-catalyzed reaction of ethylbenzene with bromine, and show why the sigma complex (and the transition state leading to it) is lower in energy for...
Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the position. Predict the major products of the reactions of naphthalene with the following reagents....