The normal boiling point for acetone is 56.5oC. At an elevation of 5300 ft, the atmospheric pressure is 630 torr. What would be the boiling point of acetone (Hvap = 32.0 kJ/mol) at this elevation?...
The 1H NMR spectra of three isomers with molecular formula C4H9Br are shown here. Which isomer produces which spectrum? a. b. c. (ppm) -frequency o (ppm) frequency 5 2 (ppm) frequency
The rotational constant for CO is 1.9314 cm-1 and 1.6116 cm-1 in the ground and first excited vibrational states, respectively. By how much does the intern clear distance change as a result of this...
Compound A, C 8 H 10 O 2 , has an intense JR absorption at 1750 cm ?1 and gives the 13 C NMR spectrum shown. Propose a structure for A. 219 8 TMS 200 180 160 140 120 40 O ppm 80 60 20 100 Chemical...
Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B...
Write structural formulas or make molecular models for all the compounds that are trichloro derivatives of cyclopropane. (Dont forget to include stereoisomers.) Which are chiral? Which are achiral?
The pH of human blood is steady at a value of approximately 7.4 owing to the following equilbrium reactions: CO2(aq) + H2O(l) H2CO3(aq) HCO3-(aq) + H+(aq) Acids formed during normal celluar...
An amine A has the molecular formula C7H9N. Compound A reacts with benzenesulfo-nyl chloride in aqueous potassium hydroxide to give a clear solution; acidification of the solution gives a...
For a first-order phase transition, to which the Clapeyron equation does apply, prove the relation C3 = CP - aVurH/urs V Where Cs = (q/T) s is the heat capacity along the coexistence curve of two...
Show how you would convert benzaldehyde into each of the following. You may use any other needed reagents, and more than one step may be required. (a) Benzyl alcohol (b) Benzoic acid (c) Benzoyl...
What is the principal organic product formed in the reaction of ethylene oxide with each of the following? (a) Sodium cyanide (NaCN) in aqueous ethanol (b) Sodium azide (NaN3) in aqueous ethanol (c)...
The FEMO theory (Problem 11.14) of conjugated molecules is rather crude and better results are obtained with simple Huckel theory. (a) For a linear conjugated polyene with each of N carbon atoms...
(a) Given H for the reaction H2 (g) + O2 (g) H2O (l) H = -286 kJ Along with the information that the heat of combustion of ethane is 1560 kJ/mol and that of ethylene is 1410 kJ/mol, calculate H for...
The addition of hydrogen halides to alkenes has played a fundamental role in the investigation of organic reaction mechanisms. In one study (M.J. Haugh and D.R. Dalton, J. Amer. Chem. Sac. 97, 5674...
Potassium superoxide, KO2, is employed in a selfcontained breathing apparatus used by emergency personnel as a source of oxygen. The reaction is 4KO2(s) + 2H2O(l) 4KOH(s) + 3O2(g) Say a...
Draw four reasonable resonance structures for the PO3F2- ion. The central P atom is bonded to the three O atoms and to the F atom. Show formal charges.
Calculate the molar volume of chlorine gas at 350 K and 2.30 atm using (a) The perfect gas law and (b) The van der Waals equation. Use the answer to (a) to calculate a first approximation to the...
Suppose that you are a colour chemist and had been asked to intensify the colour of a dye without changing the type of compound, and that the dye in question was a polyene. Would you choose to...
When o-phthalaldehyde is treated with base, o-(hydroxymethyl) benzoic acid is formed. Show the mechanism of this reaction. CO2H 1. "OH 2. * " "CH2 o-Phthalaldehyde o-(Hydroxymethyl)benzoic acid
A single epoxide was isolated in 7984% yield in the following reaction. Was this epoxide A or B? Explain your reasoning.
Strontianite (strontium carbonate) is an important mineral of strontium. Calculate the solubility of strontium carbonate, SrCO3, from the solubility product constant (see Table 17.1). TABLE 17.1...
A certain compound A, when treated with N-bromosuccinimide and benzoyl peroxide under photochemical conditions in refluxing carbon tetrachloride, gave 3, 4, 5-tribromobenzyl bromide in excellent...
Peroxyacetyl nitrate, or PAN, is present in photochemical smog. Draw Lewis structures (including resonance forms) for PAN. The skeletal arrangement is H O 8 0 O-O
Write the structure of the major organic product isolated from the reaction of 3-hexyne with (a) Hydrogen (2 mol), platinum (b) Hydrogen (1 mol), Lindlar palladium (c) Lithium in liquid ammonia (d)...
A glass tumbler containing 243 cm3 of air at 1.00 102 kPa (the barometric pressure) and 20oC is turned upside down and immersed in a body of water to a depth of 20.5 m. The air in the glass is...
Another alternative refrigerant (see preceding problem) is 1,1,1,2- tetrafluoroethane (refrigerant HFC-134a). Tillner-Roth and Baehr published a compendium of thermo physical properties of this...
The standard enthalpy of a certain reaction is approximately constant at + 125 k] mol-l from 800 K up to 1500 K. The standard reaction Gibbs energy is +22 kJ mol-1 at 1120 K. Estimate the temperature...
Cholesterol, when isolated from natural sources, is obtained as a single enantiomer. The observed rotation _ of a 0.3-g sample of cholesterol in 15 mL of chloroform solution contained in a 10-cm...
Each of the following compounds is characterized by a 1H NMR spectrum that consists of two peaks, both singlets, having the chemical shifts indicated. Identify each compound. (a) C6H8; 2.7 ppm (4H)...
How would you synthesize the following compounds from Cyclohexanone? (a) 1-Methylcyclohexane (b) 2-Phenylcyclohexanone (c) cis-1, 2-Cyclohcxanediol (d) 1-Cyclohexylcyclohcxanol
Starting with methyl propanoate, how could you prepare 4-methyl-3-heptanone? CH3CH3COCH3CH3CH CCHCH CH2CH3 methyl propanoate CH3 4-methyl-3-heptanone
Each of the following reactions has been reported in the chemical literature and gives a single organic product in high yield. Write the structure of the product for each reaction. (a)...
The molar heat capacity of lead varies with temperature as follows: TIK 10 15 20 25 30 50 Cp,m/O K-1 rnol-1) 2.8 7.0 10.8 14.1 16.5 21.4 TIK 70 100 150 200 250 298 Cp,m/OK-1 mol-1) 23.3 24.5 25.3...
Consider the substances in Table 9.3. Which substance requires the largest amount of energy to raise the temperature of 25.0 g of the substance from 15.0oC to 37.0oC? Calculate the energy. Which...
What carbonyl compounds would you reduce to prepare the following alcohols? List all possibilities. (b) CH |(a) (c) H CHCH2CH2H2H2 C CHCH-CH
Rank the following substances in order of increasing acidity: C CH3CH3 CHCCH2CCH Acetic acid (pKa = 4.76) Phenol Acetone (pKa = 19.3) 2,4-Pentanedione (pKa = 9) (pKa = 9.9) %3D %3D
The work function for metallic cesium is 2.14 eV. Calculate the kinetic energy and the speed of the electrons ejected by light of wavelength (a) 700 nm, (b) 300 nm.
Give the structure and name of each of the following aromatic hydrocarbons: a. C8H10; has two possible ring-substituted monobromo derivatives b. C9H12; can give only one mononitro product after...
When light of wavelength 400 nm passes through 3.5 mm of a solution of an absorbing substance at a concentration 0.667 mmol dm-3, the transmission is 65.5 per cent. Calculate the molar absorption...
Draw and name all possible stereoisomers of (CH3)2CHCHBrCHClCH3.
Write structural formulas for all the alkynes of molecular formula C8H14 that yield 3-ethylhexane on catalytic hydrogenation.
Suppose that S is regarded as a function of P and T. Show that TdS= CpdT- aTVdp. Hence, show that the energy transferred as heat when the pressure on an incompressible liquid or solid is increased by...
At 90C, the vapour pressure of I, 2-dimethylbenzene is 20 kPa and that of 1,3-dimethylbenzene is 18 kPa. What is the composition of a liquid mixture that boils at 90C when the pressure is 19 kPa?...
Aldol condensation of 3-methylcyclohexanone leads to a mixture of two enone products, not counting double-bond isomers draw them.
Compare 2, 3-pentanediol and 2, 4-pentanediol with respect to the number of stereoisomers possible for each constitution. Which stereoisomers are chiral? Which are achiral?
A. Akgerman and M. Zardkoohi (J. Chem. Eng. Data 41,185 (1996)) examined the adsorption of phenol from aqueous solution on to fly ash at 20e. They fitted their observations to a Freundlich isotherm...
C6H4NH2COOH, para-aminobenzoic acid (PABA), is used in some sunscreen agents. Calculate the concentrations of hydronium ion and para-aminobenzoate ion, C6H4NH2COO, in a 0.055 M solution of the acid....
Propose a structure for an alcohol with molecular formula C5H12 O that has the 1H NMR spectrum given in Fig. 9.46. Assign the chemical shifts and splitting patterns to specific aspects of the...
Take nitrogen to be a van der Waals gas with a = 1.352 dm6 atm mol-2 and b = 0.0387 dm3 mol-1, and calculate Hm when the pressure on the gas is decreased from 500 atm to 1.00 atm at 300 K. For a van...
Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, IICN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal...
Predict the shape of the nitronium ion, NO from its Lewis structure and the VSEPR model. It has one Raman active vibrational mode at 1400 cm-1, two strong IR active modes at 2360 and 540 cm-1, and...
Epoxides are reduced by treatment with lithium aluminum hydride to yield alcohols. Propose a mechanism for thisreaction. 1. LIAIH4, ether 2. H*
Sodium metal reacts vigorously with water. A piece of sodium weighing 19.70 g was added to a beaker containing 126.22 g of water. During reaction, hydrogen gas was produced and bubbled from the...
Even though the methyl group occupies an equatorial site, the conformation shown is not the most stable one for methylcyclohexane. Explain.
The molar mass of an enzyme was determined by dissolving it in water, measuring the osmotic pressure at 20C, and extrapolating the data to zero concentration. The following data were obtained: c/(mg...
In regions with dry climates, evaporative coolers are used to cool air. A typical electric air conditioner is rated at 1.00 104 Btu/ h (1 Btu, or British thermal unit, equals the amount of energy...
How would you use a Grignard reaction on an aldehyde or ketone to synthesize the following compounds? (a) 2-Pentanol (b) 1-Butanol (c) 1-Phenylcyclohexanol (d) Diphenyl methanol
Outline a synthesis of propene from each of the following: (a) Propyl chloride (b) Isopropyl chloride (c) Propyl alcohol (d) Isopropyl alcohol (e) 1, 2-Dibromopropane (f) Propyne
A standard method for the preparation of sodium cyclopentadienide (C5H5Na) is by reaction of cyclopentadiene with a solution of sodium amide in liquid ammonia. Write a balanced equation for this...
How would you synthesize the following substances starting from benzene or phenol? Assume that ortho- and Para-substitution products can be separated. (a) o-Bromobenzoic acid (b) p-Methoxytoluene (c)...
Sulfuryl chloride is used in organic chemistry as a chlorinating agent. At moderately high temperatures it decomposes as follows: with Kc = 0.045 at 650 K. a. A sample of 8.25 g of SO2Cl2 is placed...
The rate constant for the decomposition of a certain substance is 1.70 x 10-2 dm3 mol-1 S-1 at 24C and 2.01 X 10-2 dm3 mol-1 S-1 at 37"C. Evaluate the Arrhenius parameters of the reaction.
Spinel is a mineral that contains 37.9% Al, 17.1% Mg, and 45.0% O, by mass, and has a density of 3.57 g/cm3. The unit cell is cubic with an edge length of 8.09 . How many atoms of each type are in...
You have the mythical metal element X that can exist as X+, X2+, and X5+ ions. a. What would be the chemical formula for compounds formed from the combination of each of the X ions and SO42? b. If...
If 123 g of C10H16O are dissolved in 355 g of C6H6, what is the freezing point of this solution?
Predict the masses and the structures of the most abundant fragments observed in the mass spectra of the following compounds. (a) 2-methylpentane (b) 3-methylhex-2-ene (c) 4-methylpentan-2-ol (d)...
Divide the following compounds into groups that might be expected to exhibit similar chemical behavior: a. C4H10 b. CH3OCH3 c. C3H7OH d. C8H18 e. HOCH2CH2CH2OH f. CH3NH2 g. CH3CH2CH3 h. CH3OH i....
A first -order decomposition reaction is observed to have the following rate constants at the indicated temperatures. Estimate the activation energy. k/(10-3 s-1) 2.46 45.1 576 0/C 20.0 40.0
The observed rotation of 2.0 g of a compound in 50 mL of solution in a polarimeter tube 50-cm long is +13.4o What is the specific rotation of the compound?
Give IUPAC names for the following compounds: o (c) CHH2H2 CH2CH3 (a) (b) CH3CH2CHCHI NH2 (d) (e) (f) CH3CHCH,NHCH3 CH-CH-C H CH Br (h) (g) SCH(CH3)2
Calculate the magnitude of the diffusion-controlled rate constant at 298 K for the recombination of two atoms in benzene, for which 17 = 0.601 cP. Assuming the concentration of the reacting species...
Treatment of an ?, ? unsaturated ketone with basic aqueous hydrogen peroxide yields an epoxy ketone. The reaction is specific to unsaturated ketones; isolated alkene double bonds do not react....
A chemist in need of 2, 2-dimethylpentanoic acid decided to synthesize some by reaction of 2chloro-2-methylpen Lane with NaCN, followed by hydrolysis of the product. After the reaction sequence was...
Electrostatic potential maps of a typical amide (acetamide) and an acyl azide (acetyl azide) are shown. Which of the two do you think is more reactive in nucleophilic acyl substitution reactions?...
The compound MON-0585 is a nontoxic, biodegradable larvicide that is highly selective against mosquito larvae. Synthesize MON-0585 using either benzene or phenol as a source of the aromaticrings....
Iron(III) chloride is reduced by tin(II) chloride. 2FeCl3(aq) + SnCl2(aq) 2FeCl2(aq) + SnCl4(aq) The concentration of Fe3+ ion at the beginning of an experiment was 0.03586 M. After 4.00 min, it was...
Predict the product of the reaction of valine with the following reagents: (a) CH3CH2OH, acid (b) Di-tert-butyl dicarbonate (c) KOH, H2O (d) CH3COCl, pyridine then H2O
Calculate the change in chemical potential of a perfect gas when its pressure is increased isothermally from 92.0 kPa to 252.0 kPa at 50C.
How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (a) 1-Bromohexane (e)...
Normalize the following wave functions: (a) Sin (nx/L) in the range 0
Identify the most acidic hydrogens in each of the following molecules: (a) CH3CH2CHO (b) (CH3) CH3CCOCH3 (c) CH3CO2H (d) Benz amide (e) CH3CH2CH2CN (f) CH3CON (CH3)2
An alloy of iron (54.7%), nickel (45.0%), and manganese (0.3%) has a density of 8.17 g/cm3. How many iron atoms are there in a block of alloy measuring 10.0 cm 20.0 cm 15.0 cm?
Predict the products of reaction of pent-1-yne with the following reagents. (a) 1 equivalent of HCl (b) 2 equivalents of HCl (c) excess H2, Ni (d) H2, Pd/BaSO4. quinoline (e) I equivalent of Br2 (f)...
How would you prepare the following substances from 1-butanol? (a) Butyl amine (b) Dibutyl amine (c) Propyl amine (d) Pentylamine (e) N, N-Dimethyl butyl amine (f) Propene
What product would you expect from Hofmann elimination of a heterocyclic amine such as piperidine? Write all thesteps? Piperidine
How would you prepare the following substances from Cyclopentanol? More than one step may be required. (a) Cyclopentanone (b) Cyclopentane (c) 1-Methylcyclopentanol (d) Trans-2-Methylcyclopentanol I...
The dimerization of butadiene was studied at 500. K: 2C4H6(g) C8H12(g) The following data were obtained, where Determine the forms of the integrated rate law, the differential rate law, and the value...
Under acid catalysis, tetrahydrofurfuryl alcohol reacts to give surprisingly good yields of dihydropyran. Propose a mechanism to explain this useful synthesis. Ht tetrahydrofurfuryl alcohol...
A certain sample of coal contains 1.6 percent sulfur by mass. When the coal is burned, the sulfur is converted to sulfur dioxide. To prevent air pollution, this sulfur dioxide is treated with calcium...
Cyclopentyl methyl ketone has been prepared from 1, 4-dibromobutane and ethyl acetoacetate. Outline the steps in this synthesis by writing a series of equations showing starting materials, reagents,...
Calculate the change in entropy when 50 k] of energy is transferred reversibly and isothermally as heat to a large block of copper at (a) OC, (b) 70e
An electronically excited state of Hg can be quenched by N, according to Hg* (g) + Nz (g, V = 0) -7 Hg (g) + N, (g, v = 1) in which energy transfer from Hg* excites Nz vibrationally. Fluorescence...
The following alkyl bromide can be prepared by reaction of the alcohol (S)-2-pentanol with PBr3. Name the compound, assign (R) or (S) stereochemistry, and tell whether the reaction of the alcohol...
Two liquids, A and B, show partial miscibility below 52.4C. The critical concentration at the upper critical temperature is x = 0.459, where x is the mole fraction of A. At 40.0C the two solutions in...
Plasma is a state of matter consisting of positive gaseous ions and electrons. In the plasma state, a mercury atom could be stripped of its 80 electrons and therefore would exist as Hg80+. Use the...
Calculate Ka for each of the following acids, given its pKa. Rank the compounds in order of decreasing acidity. (a) Aspirin: pKa = 3.48 (b) Vitamin C (ascorbic acid): pKa = 4.17 (c) Formic acid...
At 300 K and 20 atm, the compression factor of a gas is 0.86. Calculate (a) The volume occupied by 8.2 mmol of the gas under these conditions and (b) An approximate value of the second virial...
Arrange the following compounds or anions in each group in order of decreasing basicity: (a) H3C-, H2N-, HO-, F- (b) H2O, NH3, HO-, H2N- (c) HO-, H2N-, C N, NO3
The dissociation vapour pressure ofNH4Cl at 427C is 608 kPa but at 459C it has risen to 1115 kPa. Calculate (a) The equilibrium constant, (b) The standard reaction Gibbs energy, (c) The standard...
Consider the hypothetical reaction B E + F which is assumed to occur by the mechanism Where B* represents a B molecule with enough energy to surmount the reaction energy bar70. Consider the following...