Each of the following compounds is characterized by a 1H NMR spectrum that consists of only a single peak having the chemical shift indicated. Identify each compound. (a) CsHis; 80.9 ppm (b) C,H10, ...

Deduce the structure of each of the following compounds on the basis of their 1H NMR spectra and molecular formulas: (a) C8H10; 1.2 ppm (triplet, 3H) δ2.6 ppm (quartet, 2H)...

Write the structure of the Grignard reagent formed from each of the following compounds on reaction with magnesium in diethyl ether: (a) Allyl chloride (b) Iodocyclobutane (c) 1-Bromocyclohexene

A similar conclusion may be drawn by considering the reactions of the cis and trans isomers of 4-tert-butylcyclohexanol with acetic anhydride. On the basis of the information just presented, predict...

Each of the following ethers has been shown to be or is suspected to be a mutagen, which means it can induce mutations in test cells. Write the structure of each of these ethers. (a)...

Show how 2-butanone could be prepared by a procedure in which all of the carbons originate in acetic acid (CH3CO2H).

Prepare each of the following compounds from the starting materials given and any necessary organic or inorganic reagents: (a) (b) (c) CH3 CH3)2CHCHCCH2OH from (CH CHCH2OH , C&HCH-CCH,OH from benzyl...

-lodo acids are not normally prepared by direct iodination of carboxylic acids under conditions of the Hell-Volhard-Zelinsky reaction. Show how you could convert octadecanoic acid to its 2-iodo...

Show how butanoic acid may be converted to each of the following compounds: (a) 1-Butanol (b) Butanal (c) 1-Chlorobutane (d) Butanoyl chloride (e) Phenyl propyl ketone (f) 4-Octanone (g)...

Show by a series of equations, using any necessary organic or inorganic reagents, how acetic acid can be converted to each of the following compounds: (a) H2NCH2CO2H (b) C6H5OCH2CO2H (c) NCCH2CO2H...

On the basis of the general mechanism for amide hydrolysis in acidic solution shown in Figure 20.6, write an analogous sequence of steps for the hydrolysis of acetanilide,

Using ethanol as the ultimate source of all the carbon atoms, along with any necessary inorganic reagents, show how you could prepare each of the following: (a) Acetyl chloride (b) Acetic anhydride...

The preparation of cis-4-tert-butylcyclohexanol from its trans stereoisomer was carried out by the following sequence of steps. Write structural formulas, including stereochemistry, for compounds A...

Each of the following dihaloalkanes gives an N-(haloalkyl)phthalimide on reaction with one equivalent of the potassium salt of phthalimide. Write the structure of the phthalimide derivative formed in...

Identify the principal organic products of each of the following reactions: (a) (b) (c) (d) (e) (f) (g) Cyclohexanone +cyclohexylamine I LiAIH4 NCH,CHsHO. HO I. p-toluenesulfonyl chloride, pyridine...

As the extent of electron delocalization into the ring increases, the geometry at nitrogen flattens. p-Nitroaniline, for example, is planar. Write a resonance form for p-nitroaniline that shows how...

Each of the following compounds has been prepared from o-anisidine (o-methoxyaniline). Outline a series of steps leading to each one. (a) o-Bromoanisole (b) o-Fluoroanisole (c)...

ssEach of the following reactions has been reported in the chemical literature and proceeds in good yield. Identify the principal organic product of each reaction. (a) (b) (c) (d) (e) Product of part...

Design syntheses of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (a) p-Aminobenzoic acid from p-methylaniline (b) (c)...

Ammonia and amines undergo conjugate addition to ,-unsaturated carbonyl compounds (Section 18.12). On the basis of this information, predict the principal organic product of each of the following...

Predict the major organic product in each of the following reactions: (a) (b) (c) (d) (e) (f) Cl NO2 CH3 Cl H,NNH triethylene glycol NO2 Cl CI L. HNO, H SO. 120C 2. NH, ethylene glycol, 140C CF3 L...

Another hexose gives the same aldaric acid on oxidation as does D-glucose. Which one? CHO OH HO,C HO HO HO OH OH OH CO2H Fischer projection of D-glucuronic acid B-Pyranose form of D-glucuronic acid

Aspirin or acetyl salicylic acid is synthesized by reacting salicylic acid with acetic anhydride: (a) How much salicylic acid is required to produce 0.400 g of aspirin (about the content in a...

Which of the following metals can react with water? (a) Au, (b) Li, (c) Hg, (d) Ca, (e) Pt.

Determine how many grams of each of the following solutes would be needed to make 2.50 x 102 mL of a 0.100 M solution: (a) Cesium iodide (CsI), (b) Sulfuric acid (H2SO4), (c) Sodium carbonate...

A 35.2-mL, 1.66 M KMnO4 solution is mixed with 16.7mL of 0.892 M KMnO4 solution. Calculate the concentration of the final solution.

Which of the following diagrams best represents the hydration of NaCl when dissolved in water? The Cl2 ion is larger in size than the Na1 ion. (b) (c) (a)

Sodium bicarbonate (NaHCO3) is called baking soda because when heated, it releases carbon dioxide gas, which is responsible for the rising of cookies, doughnuts, and bread. (a) Calculate the volume...

An equimolar mixture of H2 and D2 effuses through an orifice (small hole) at a certain temperature. Calculate the composition (in mole fractions) of the gas that pass through the orifice. The molar...

A sample of ammonia (NH3) gas is completely decomposed to nitrogen and hydrogen gases over heated iron wool. If the total pressure is 866 mmHg, calculate the partial pressures of N2 and H2.

A sample of nitrogen gas expands in volume from 1.6 L to 5.4 L at constant temperature. Calculate the work done in joules if the gas expands (a) Against a vacuum, (b) Against a constant pressure of...

A sheet of gold weighing 10.0 g and at a temperature of 18.0C is placed fl at on a sheet of iron weighing 20.0 g and at a temperature of 55.6C. What is the final temperature of the combined metals?...

Pentaborane-9,B5H9, is a colorless, highly reactive liquid that will burst into flame when exposed to oxygen. The reaction is 2B5H9(l) + 12O2(g) - 5B2O3(s) + 9H2O(l) Calculate the kilojoules of heat...

A person ate 0.50 pound of cheese (an energy intake of 4000 kJ). Suppose that none of the energy was stored in his body. What mass (in grams) of water would he need to perspire in order to maintain...

An electron in a hydrogen atom is excited from the ground state to the n = 4 state. Comment on the correctness of the following statements (true or false). (a) n = 4 is the first excited state. (b)...

Alveoli are the tiny sacs of air in the lungs whose average diameter is 5.0 10-5 m. Consider an oxygen molecule (5.3 10-26 kg) trapped within a sac. Calculate the uncertainty in the velocity of the...

Arrange the following in order of increasing boiling point: RbF, CO2, CH3OH, CH3Br. Explain your reasoning?

A length of wire is placed on top of a block of ice. The ends of the wire extend over the edges of the ice, and a heavy weight is attached to each end. It is found that the ice under the wire...

A miner working 260 m below sea level opened a carbonated soft drink during a lunch break. To his surprise, the soft drink tasted rather "flat." Shortly afterward, the miner took an elevator to the...

The solubility of CO2 in water at 25C and 1 atm is 0.034 mol/L. What is its solubility under atmospheric conditions? (The partial pressure of CO2 in air is 0.0003 atm.) Assume that CO2 obeys Henry's...

The vapor pressure of benzene is 100.0 mmHg at 26.1C. Calculate the vapor pressure of a solution containing 24.6 g of camphor (C10H16O) dissolved in 98.5 g of benzene. (Camphor is a low-volatility...

A solution of 2.50 g of a compound having the empirical formula C6H5P in 25.0 g of benzene is observed to freeze at 4.3C. Calculate the molar mass of the solute and its molecular formula.

A solution of 6.85 g of a carbohydrate in 100.0 g of water has a density of 1.024 g/mL and an osmotic pressure of 4.61 atm at 20.0C. Calculate the molar mass of the carbohydrate.

"Time-release" drugs have the advantage of releasing the drug to the body at a constant rate so that the drug concentration at any time is not too high as to have harmful side effects or too low as...

The equilibrium constant (Kc) for the reaction is 4.17 10-34 at 25C. What is the equilibrium constant for the reaction at the same temperature? 2HC(g) H2(g) + Cl2(g) H2(g) CL2(g) 2HCI(g)

A reaction vessel contains NH3, N2, and H2 at equilibrium at a certain temperature. The equilibrium concentrations are [NH3] = 0.25 M, [N2] = 0.11 M, and [H2] = 1.91 M. Calculate the equilibrium...

Consider the heterogeneous equilibrium process: At 700°C, the total pressure of the system is found to be 4.50 atm. If the equilibrium constant KP is 1.52, calculate the equilibrium partial...

Consider the reaction Comment on the changes in the concentrations of SO2, O2, and SO3 at equilibrium if we were to (a) Increase the temperature; (b) Increase the pressure; (c) Increase SO2; (d) Add...

A 0.1276-g sample of an unknown monoprotic acid was dissolved in 25.0 mL of water and titrated with 0.0633 M NaOH solution. The volume of base required to bring the solution to the equivalence point...

A volume of 75 mL of 0.060 M NaF is mixed with 25 mL of 0.15 M Sr(NO3)2. Calculate the concentrations in the final solution of NO32, Na1, Sr21, and F2. (Ksp for SrF2 5 2.0 3 10210.)

A galvanic cell is constructed as follows. One half cell consists of a platinum wire immersed in a solution containing 1.0 M Sn2+ and 1.0 M Sn4+; the other half-cell has a thallium rod immersed in a...

How many geometric isomers are in the following species? (a) [Co(NH3)2Cl4]-, (b) [Co(NH3)3Cl3]

Aqueous copper(II) sulfate solution is blue in color. When aqueous potassium fluoride is added, a green precipitate is formed. When aqueous potassium chloride is added instead, a bright-green...

A radioactive substance undergoes decay as follows: Time (days) Mass (g) 0 ..................... 500 1 ..................... 389 2 ..................... 303 3 ..................... 236 4...

A compound having the molecular formula C4H10O does not react with sodium metal. In the presence of light, the compound reacts with Cl2 to form three compounds having the formula C4H9OCl. Draw a...

An alcohol was converted to a carboxylic acid with acidic potassium dichromate. A 4.46-g sample of the acid was added to 50.0 mL of 2.27 M NaOH and the excess NaOH required 28.7 mL of 1.86 M HCl for...

Tell whether the Ha and Hb hydrogens in each of the following compounds are enantiotopic, diastereotopic, or neither. a. b. c. d. CH3CH2CCH3 HV HI Br Hb H3C -

The observed relative reactivities of primary, secondary, and tertiary alcohols with a hydrogen halide are 3o> 2o> 1o.If secondary alcohols underwent an reaction rather than an reaction with a...

Starting with benzene, show how meta-aminoanisole could be prepared via a synthesis that a. Involves a benzyne intermediate b. Does not involve a benzyne intermediate

Name the following compounds: a. b. c. d. e. f. g. h. i. COOH Br Br Br Br CH3 ,. CHCH NO. OCH, CH2CH3 SOH CI CI CH3 CH2CH3 Cl

Propose a reasonable mechanism for each of the following reactions: a. b. HCI CH3O CH3O NH N. OH OH

Indicate how the following compounds could be synthesized from cyclohexanone and any other necessary reagents: a. b. c. d. e. f. CH2CH CH CH3 0 CCH-CH,CH, (two ways) CH2CH2 COCH,CH

A carboxylic acid is formed when an α haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for the following Favorskii reaction....

Name the following compounds: a. b. c. d. e. f. CH3 CH3 CH2CH3 CH3 HN CH3 CH3 CH3 CH-CH3

Name a ketose and another aldose that form the same osazone as a. D-ribose b. D-altrose c. L-idose d. D-galactose

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...

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...

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.

Natural epinephrine, [a]D25oC = -50, is used medicinally. Its enantiomer is medically worthless and is. in fact, toxic. You, a pharmacist, are given a solution said to contain 1 g of epinephrine in...

Sodium hydrogen (S)-glutamate [(S)-monosodium glutamate], [a] D 25oC = +24, is the active flavor enhancer known as MSG. The condensed formula of MSG is shown in the margin, (a) Draw the structure of...

Studies have shown that one stereoisomeric certain types of neurodegenerative disorders, system, as illustrated in structure B, and that form of compound A is an effective agent against Recognize...

Which reaction intermediate is involved in the following reaction? (a) A secondary radical (b) A tertiary radical (c) A secondary carbocation (d) A tertiary carbocation Br. hv...

Write an appropriate equation to show how each of the following alcohols acts as, first, a base, and, second, an acid in solution. How do the base and acid strengths of each compare with those of...

Give the major product(s) expected from each of the reactions shown below. Watch stereochemistry. (a) (b) H111 H-C CH 0 H11" H3C

Your team has been asked to devise a synthesis of the tertiary alcohol 2-cyclohexyl-2-butanol, A. Your laboratory is well stocked with the usual organic and inorganic reagents and solvents. An...

Ester hydrolysis is best illustrated by (a) (b) (c) (d) H, H,O CH OCCH CH,OCH CO 0 CH OCCH, H.HO CH3OCCH, CH3OH + HOCCH, H.O HO

For each of the following alcohols, write the structure of the alkyloxonium ion produced after pro-tonation by strong acid; if the alkyloxonium ion is capable of losing water readily, write the...

One of the following compounds will show a doublet as part of its 'H NMR spectrum. Which one? (a) CH4 (b) ClCH(CH3)2 (c) CH3CH2CH3 (d) HC-CH Br Br

Write the structures of as many simple alkenes as you can that, upon catalytic hydrogenation with H2 over Pt. will give as the product (a) 2-methylbutane: (b) 2.3-dimethylbutane; (c)...

What key structural feature distinguishes haloalkanes that give more than one stereoisomer on E2 elimination from those that give only a single isomer exclusively?

Write the most likely major product(s) of each of the following haloalkanes with sodium ethoxide in ethanol or potassium tert-butoxide in 2-methyl-2-propanol (tert-butyl alcohol), (a) Chloromethane;...

Below are shown three C4H8C12 isomers on the left and three sets of 1H NMR data that one would expect on application of the simple N + 1 rule on the right. Match the structures to the proper spectral...

The 1H NMR spectrum of 1-chloropentane is shown at 60 MHz (spectrum H) and 500 MHz (spectrum I), Explain the differences in appearance of the two spectra, and assign the signals to specific hydrogens...

Study of the solvolysis of derivatives of menthol [5-methyl 2 (I methylethyl) cyclohexanol] has greatly enhanced our understanding of these types of reactions. Heating the isomer of the...

An organic compound exhibits IR spectrum F. From the group of structures below, choose one that matches the spectrum best. 0CH3 100 IR 0 4000 3500 3000 2500 2000 1500 1000 600 cm-1 Wavenumber

Calculate the degree of un-saturation that corresponds to each of the following molecular formulas, (a) C7H12 (b) C8H7NO2; (c) C6C16; (d) C10H22O11 (e) C6H10S; (f) C18H28O2

Name each of the compounds below. Use cis / trans and/or E/Z designations, if appropriate, to designate stereochemistry a. b. c. Cl C=C H,C CH3 CH2CI H3C H3C H,C Cl

All the parts of this problem refer to the alkane having the carbon skeleton shown.

N-Butyl mercaptan is the common name of a foul-smelling substance obtained from skunk fluid. It is a thiol of the type RX, where R is an n-butyl group and X is the functional group that characterizes...

(a) Write Newman projections for the gauche and anti conformations of 1, 2-dichloroethane (ClCH2CH2Cl). (b) The measured dipole moment of ClCH2CH2Cl is 1.12 D. Which one of the following statements...

Which of the structures shown for the axial conformation of methylcyclohexane do you think is more stable, A or B? Why?

As noted in Problem 4.7, hydrogen cyanide (HCN) has a pKa of 9.1. Is cyanide ion (CN) a stronger base or a weaker base than hydroxide ion (HO)?

Assuming the relative rate of secondary to primary hydrogen atom abstraction to be the same in the chlorination of propane as it is in that of butane, calculate the relative amounts of propyl...

Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields (a) A single monochloride (c) Four isomeric monochlorides (b) Three isomeric...

Arrange the following alkenes in order of decreasing stability: 1-pentene; (E)-2-pentene; (Z)-2-pentene; 2-methyl-2-butene.

Give the IUPAC names for each of the following compounds: (a) (CH3CH2)2C = CHCH3 (b) (CH3CH2)2C = C (CH2CH3)2 (c) (CH3)3CCH = CCl2

(a) Suggest an explanation for the fact that 1-methylcyclopropene is some 42 kJ/mol (10 kcal/mol) less stable than methylenecyclopropane

(a) The sex attractant of the Mediterranean fruit fly is (E)-6-nonen-1-ol. Write a structural formula or build a molecular model for this compound, showing the stereochemistry of the double bond. (b)...

(a) Write the structures or build molecular models of all the isomeric alcohols having the molecular formula C5H12O. (b) Which one will undergo acid-catalyzed dehydration most readily? (c) Write the...