Give the structures of the likely products from reaction of 1 equivalent of HCl with 2-methyl-1,3-cyclohexadiene. Show both 1,2 and 1,4 adducts.
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Textbook Solutions for Organic Chemistry
Question
A solution was prepared by mixing 50.00 mL of 0.100 M HNO3 and 100.00 mL of 0.200 M HNO3. Calculate the molarity of the final solution of nitric acid.
Solution
The first step in solving 14 problem number 142 trying to solve the problem we have to refer to the textbook question: A solution was prepared by mixing 50.00 mL of 0.100 M HNO3 and 100.00 mL of 0.200 M HNO3. Calculate the molarity of the final solution of nitric acid.
From the textbook chapter The proton NMR spectrum of a compound with the formula C7H12O2 is shown. The infrared spectrum displays a strong band at 1738 cm21 and a weak band at 1689 cm21. The normal carbon-13 and the DEPT experimental results are tabulated. Draw the structure of th you will find a few key concepts needed to solve this.
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Solution: A solution was prepared by mixing 50.00 mL of
Chapter 14 textbook questions
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Chapter 14: Problem 14 Organic Chemistry 9
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Chapter 14: Problem 14 Organic Chemistry 9
Give the structures of both 1,2 and 1,4 adducts resulting from reaction of 1 equivalent of HCl with 1,3-pentadiene.
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Chapter 14: Problem 14 Organic Chemistry 9
Look at the possible carbocation intermediates produced during addition of HCl to 1,3-pentadiene (Problem 14-2), and predict which 1,2 adduct predominates. Which 1,4 adduct predominates?
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Chapter 14: Problem 14 Organic Chemistry 9
Give the structures of both 1,2 and 1,4 adducts resulting from reaction of 1 equivalent of HBr with the following compound:
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Chapter 14: Problem 14 Organic Chemistry 9
The 1,2 adduct and the 1,4 adduct formed by reaction of HBr with 1,3-butadiene are in equilibrium at \(\mathrm{40~^\circ C}\). Propose a mechanism by which the interconversion of products takes place. Equation Transcription: Text Transcription: 40^oC
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Chapter 14: Problem 14 Organic Chemistry 9
Why do you suppose 1,4 adducts of 1,3-butadiene are generally more stable than 1,2 adducts?
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Chapter 14: Problem 14 Organic Chemistry 9
Predict the product of the following Diels–Alder reaction:
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Chapter 14: Problem 14 Organic Chemistry 9
Predict the product of the following Diels–Alder reaction: Equation Transcription: Text Transcription: C=C H_3C C-OCH_3
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following alkenes would you expect to be good Diels–Alder dienophiles? ________________ Equation Transcription: Text Transcription: H_2C=CHCCl H_2C=CHCH_2CH_2COCH_3
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following dienes have an s-cis conformation, and which have an s-trans conformation? Of the s-trans dienes, which can readily rotate to s-cis?
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Chapter 14: Problem 14 Organic Chemistry 9
Predict the product of the following Diels–Alder reaction:
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Chapter 14: Problem 14 Organic Chemistry 9
Draw a segment of the polymer that might be prepared from 2-phenyl-1,3- butadiene.
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Chapter 14: Problem 14 Organic Chemistry 9
Show the mechanism of the acid-catalyzed polymerization of 1,3-butadiene.
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the energy range of electromagnetic radiation in the UV region of the spectrum from 200 to 400 nm (see Section 12-5). How does this value compare with the values calculated previously for IR and NMR spectroscopy?
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Chapter 14: Problem 14 Organic Chemistry 9
If pure vitamin A has \(\lambda_\mathrm{max}=325(\varepsilon=50,100)\), what is the vitamin A concentration in a sample whose absorbance at 325 nm is \(A=0.735\) in a cell with a pathlength of 1.00 cm? Equation Transcription: Text Transcription: lambda_max=325(epsilon=50,100) A=0.735
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following compounds would you expect to show ultraviolet absorptions in the 200 to 400 nm range? Equation Transcription: Text Transcription: CH_3
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Chapter 14: Problem 14 Organic Chemistry 9
Show the structures of all possible adducts of the following diene with 1 equivalent of HCl:
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Chapter 14: Problem 14 Organic Chemistry 9
Show the product of the Diels–Alder reaction of the following diene with 3-buten-2-one, \(\mathrm{H_2C=CHCOCH_3}\). Make sure you show the full stereochemistry of the reaction product. ________________ Equation Transcription: Text Transcription: H_2C=CHCOCH_3
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Chapter 14: Problem 14 Organic Chemistry 9
The following diene does not undergo Diels–Alder reactions. Explain.
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Chapter 14: Problem 14 Organic Chemistry 9
The following model is that of an allylic carbocation intermediate formed by protonation of a conjugated diene with HBr. Show the structure of the diene and the structures of the inal reaction products.
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Chapter 14: Problem 14 Organic Chemistry 9
Predict the major product(s) from the addition of 1 equivalent of HX and show the mechanism for each reaction below. ________________ Equation Transcription: Text Transcription: 40 ^oC CH_2 0 ^oC CH_2 CH_2
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Chapter 14: Problem 14 Organic Chemistry 9
We’ve seen that the Diels–Alder cycloaddition reaction is a one-step, peri cyclic process that occurs through a cyclic transition state. Propose a mechanism for the following reaction: Equation Transcription: Text Transcription: H_2C=CH_2
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Chapter 14: Problem 14 Organic Chemistry 9
In light of your answer to Problem 14-21 propose mechanisms for the reactions below. ________________ Equation Transcription: Text Transcription: CO_2CH_3 CO_2CH_3 CO_2CH_3 CO_2CH_3 CO_2 CH_3 CH_3 C{equiv}CH CH_3 CH_3 N_2
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Chapter 14: Problem 14 Organic Chemistry 9
Luminol, which is used by forensic scientists to find blood, fluoresces as a result of Diels–Alder-like process. The dianion of luminol reacts with \(\mathrm{O_2}\) to form an unstable peroxide intermediate that then loses nitrogen to form a dicarboxylate and emit light. The process is similar to that in 14-21 and 14-22. Propose a mechanism for this process. ________________ Equation Transcription: Text Transcription: O_2 NH_2 O^- O^- NH_2 O^- O^- N_2
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Chapter 14: Problem 14 Organic Chemistry 9
An extremely useful diene in the synthesis of many natural products is known as Danishefsky’s diene. This compound is useful because after the Diels–Alder reaction it can be converted into a product that could not be accessed by a typical Diels–Alder reaction. Show the Diels–Alder adduct and propose a mechanism that accounts for the final products. ________________ Equation Transcription: Text Transcription: OCH_3 (CH_3)_3SiO CH_2 CH_2 CH_3OH+(CH_3)_3SiCl
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Chapter 14: Problem 14 Organic Chemistry 9
Give IUPAC names for the following compounds: ________________ Equation Transcription: Text Transcription: CH_3 CH_3CH=CCH=CHCH_3 H_2C=CHCH=CHCH=CHCH_3 CH_3CH=C=CHCH=CHCH_3 CH_2CH_2CH_3 CH_3CH=CCH=CH_2
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Chapter 14: Problem 14 Organic Chemistry 9
Draw and name the six possible diene isomers of formula \(\mathrm{C_5H_8}\). Which of the six are conjugated dienes? Equation Transcription: Text Transcription: C_5H_8
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Chapter 14: Problem 14 Organic Chemistry 9
What product(s) would you expect to obtain from reaction of 1,3-cyclohexadiene with each of the following? (a) 1 mol \(\mathrm{Br_2}\) in \(\mathrm{CH_2Cl_2}\) (b) \(\mathrm{O_3}\) followed by Zn (c) 1 mol HCl in ether (d) 1 mol DCl in ether (e) 3-Buten-2-one \(\mathrm{(H_2C=CHCOCH_3)}\) (f) Excess \(\mathrm{OsO_4}\), followed by \(\mathrm{NaHSO_3}\) ________________ Equation Transcription: Text Transcription: Br_2 CH_2Cl_2 O_3 (H_2C=CHCOCH_3) OsO_4 NaHSO_3
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Chapter 14: Problem 14 Organic Chemistry 9
Electrophilic addition of \(\mathrm{Br_2}\) to isoprene (2-methyl-1,3-butadiene) yields the following product mixture: Of the 1,2-addition products, explain why 3,4-dibromo-3-methyl-1- butene (21%) predominates over 3,4-dibromo-2-methyl-1-butene (3%). Equation Transcription: Text Transcription: Br_2 Br_2 CH_3
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Chapter 14: Problem 14 Organic Chemistry 9
Propose a structure for a conjugated diene that gives the same product from both 1,2 and 1,4-addition of HBr.
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Chapter 14: Problem 14 Organic Chemistry 9
Draw the possible products resulting from addition of 1 equivalent of HCl to 1-phenyl-1,3-butadiene. Which would you expect to predominate, and why?
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Chapter 14: Problem 14 Organic Chemistry 9
Predict the products of the following Diels–Alder reactions:
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Chapter 14: Problem 14 Organic Chemistry 9
2,3-Di-tert-butyl-1,3-butadiene does not undergo Diels–Alder reactions. Explain.
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Chapter 14: Problem 14 Organic Chemistry 9
Show the structure, including stereochemistry, of the product from the following Diels–Alder reaction: Equation Transcription: Text Transcription: CH_3OC COCH_3
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Chapter 14: Problem 14 Organic Chemistry 9
How can you account for the fact that cis-1,3-pentadiene is much less reactive than trans-1,3-pentadiene in the Diels–Alder reaction?
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Chapter 14: Problem 14 Organic Chemistry 9
Would you expect a conjugated diyne such as 1,3-butadiyne to undergo Diels–Alder reaction with a dienophile? Explain.
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Chapter 14: Problem 14 Organic Chemistry 9
Reaction of isoprene (2-methyl-1,3-butadiene) with ethyl propenoate gives a mixture of two Diels–Alder adducts. Show the structure of each, and explain why a mixture is formed. Equation Transcription: Text Transcription: CO_2CH_2CH_3
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Chapter 14: Problem 14 Organic Chemistry 9
Rank the following dienophiles in order of their expected reactivity in the Diels–Alder reaction. Equation Transcription: Text Transcription: CH_3 C=C C=C C=C H_3C H_3C CH_3 CH_3
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Chapter 14: Problem 14 Organic Chemistry 9
1,3-Cyclopentadiene is very reactive in Diels–Alder cycloaddition reactions, but 1,3-cyclohexadiene is less reactive and 1,3-cycloheptadiene is nearly inert. Explain. (Molecular models are helpful.)
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Chapter 14: Problem 14 Organic Chemistry 9
1,3-Pentadiene is much more reactive in Diels–Alder reactions than 2,4-pentadienal. Why might this be? Equation Transcription: Text Transcription: CH_3
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Chapter 14: Problem 14 Organic Chemistry 9
How could you use Diels–Alder reactions to prepare the following products? Show the starting diene and dienophile in each case. ________________ Equation Transcription: Text Transcription: CO_2CH_3
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Chapter 14: Problem 14 Organic Chemistry 9
Although the Diels–Alder reaction generally occurs between an electron rich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Diels–Alder reactions between suitable electrondeicient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels–Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both. Equation Transcription: Text Transcription: CH_2 H_2C H_2C CO_2CH_3 H_2C OCH_3
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Chapter 14: Problem 14 Organic Chemistry 9
Diene polymers contain occasional vinyl branches along the chain. How do you think these branches might arise?
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Chapter 14: Problem 14 Organic Chemistry 9
Tires whose sidewalls are made of natural rubber tend to crack and weather rapidly in areas around cities where high levels of ozone and other industrial pollutants are found. Explain.
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Chapter 14: Problem 14 Organic Chemistry 9
1,3-Cyclopentadiene polymerizes slowly at room temperature to yield a polymer that has no double bonds except on the ends. On heating, the polymer breaks down to regenerate 1,3-cyclopentadiene. Propose a structure for the product.
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Chapter 14: Problem 14 Organic Chemistry 9
Arrange the molecules according to where you would expect to find their wavelength of maximum absorption in UV spectroscopy, from shortest to longest wavelength. (b) (a) (c) CH2 CH2 CH3 CH3 CH2 CH3 CH2 CH2
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following compounds would you expect to have a p n p* UV absorption in the 200 to 400 nm range? CH2 (a) (b) (c) (CH3)2C C O Pyridine A ketene
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Chapter 14: Problem 14 Organic Chemistry 9
Would you expect allene, H2CPCPCH2, to show a UV absorption in the 200 to 400 nm range? Explain.
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Chapter 14: Problem 14 Organic Chemistry 9
The following ultraviolet absorption maxima have been measured: 1,3-Butadiene 217 nm 2-Methyl-1,3-butadiene 220 nm 1,3-Pentadiene 223 nm 2,3-Dimethyl-1,3-butadiene 226 nm 2,4-Hexadiene 227 nm 2,4-Dimethyl-1,3-pentadiene 232 nm 2,5-Dimethyl-2,4-hexadiene 240 nm What conclusion can you draw about the effect of alkyl substitution on UV absorption maxima? Approximately what effect does each added alkyl group have?
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Chapter 14: Problem 14 Organic Chemistry 9
1,3,5-Hexatriene has lmax 5 258 nm. In light of your answer to Problem 14-48, approximately where would you expect 2,3-dimethyl-1,3,5- hexatriene to absorb?
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Chapter 14: Problem 14 Organic Chemistry 9
b-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of b-ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: Acetone CH3C O O CH3CCH3 CH O Malonaldehyde O O HCCH2CH Formaldehyde Pyruvaldehyde O HCH (a) How many double bonds does b-ocimene have? (b) Is b-ocimene conjugated or nonconjugated? (c) Propose a structure for b-ocimene. (d) Write the reactions, showing starting material and products
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Chapter 14: Problem 14 Organic Chemistry 9
Draw the resonance forms that result when the dienes below are protonated. If the resonance forms differ in energy, identify the most stable one. (b) (a) (c)
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Chapter 14: Problem 14 Organic Chemistry 9
Answer the questions below for 1,3,5-cycloheptatriene. (a) How many p atomic orbitals are in the conjugated system? (b) How many molecular orbitals describe the conjugated system? (c) How many molecular orbitals are bonding molecular orbitals? (d) How many molecular orbitals are anti-bonding molecular orbitals? (e) Which molecular orbitals are filled with electrons? (f) If this molecule were to absorb a photon of UV light an electron would move between which two molecular orbitals (be specif
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Chapter 14: Problem 14 Organic Chemistry 9
Treatment of 3,4-dibromohexane with strong base leads to loss of 2 equivalents of HBr and formation of a product with formula C6H10. Three products are possible. Name each of the three, and tell how you would use 1H and 13C NMR spectroscopy to help identify them. How would you use UV spectroscopy?
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Chapter 14: Problem 14 Organic Chemistry 9
Addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product. Use resonance structures to explain why none of the other regioisomer is formed. OCH3 OCH3 C
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Chapter 14: Problem 14 Organic Chemistry 9
Aldrin, a chlorinated insecticide now banned from use in the United States, can be made by DielsAlder reaction of hexachloro-1,3-cyclopentadiene with norbornadiene. What is the structure of aldrin? Norbornadiene
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Chapter 14: Problem 14 Organic Chemistry 9
Norbornadiene (Problem 14-55) can be prepared by reaction of chloroethylene with 1,3-cyclopentadiene, followed by treatment of the product with sodium ethoxide. Write the overall scheme, and identify the two kinds of reactions.
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Chapter 14: Problem 14 Organic Chemistry 9
The triene shown here reacts with 2 equivalents of maleic anhydride to yield a product with the formula C17H16O6. Predict a structure for the product. O O + 2 O C17H16O6 C CH2 H CH2
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Chapter 14: Problem 14 Organic Chemistry 9
Myrcene, C10H16, is found in oil of bay leaves and is isomeric with b-ocimene (Problem 14-50). It has an ultraviolet absorption at 226 nm and can be catalytically hydrogenated to yield 2,6-dimethyloctane. On ozonolysis followed by zinc/acetic acid treatment, myrcene yields formaldehyde, acetone, and 2-oxopentanedial: HCCH2CH2C O O O CH 2-Oxopentanedial Propose a structure for myrcene, and write the reactions, showing starting material and products.
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Chapter 14: Problem 14 Organic Chemistry 9
Hydrocarbon A, C10H14, has a UV absorption at lmax 5 236 nm and gives hydrocarbon B, C10H18, on catalytic hydrogenation. Ozonolysis of A, followed by zinc/acetic acid treatment, yields the following diketo dialdehyde: HCCH2CH2CH2C O O O CCH2CH2CH2CH O (a) Propose two possible structures for A. (b) Hydrocarbon A reacts with maleic anhydride to yield a DielsAlder adduct. Which of your structures for A is correct? (c) Write the reactions, showing the starting material and products.
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Chapter 14: Problem 14 Organic Chemistry 9
Adiponitrile, a starting material used in the manufacture of nylon, can be prepared in three steps from 1,3-butadiene. How would you carry out this synthesis? Adiponitrile H2C CHCH CH2 N CCH2CH2CH2CH2C 3 steps N
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Chapter 14: Problem 14 Organic Chemistry 9
Ergosterol, a precursor of vitamin D, has lmax 5 282 nm and molar absorptivity e 5 11,900. What is the concentration of ergosterol in a solution whose absorbance A 5 0.065 with a sample pathlength l 5 1.00 cm? Ergosterol (C28H44O) HO CH3 CH3 H H H H
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Chapter 14: Problem 14 Organic Chemistry 9
Dimethyl butynedioate undergoes a DielsAlder reaction with (2E,4E)- 2,4-hexadiene. Show the structure and stereochemistry of the product. CH3OC O C C O COCH3 Dimethyl butynedioate
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Chapter 14: Problem 14 Organic Chemistry 9
Dimethyl butynedioate also undergoes a DielsAlder reaction with (2E,4Z)-2,4-hexadiene, but the stereochemistry of the product is different from that of the (2E,4E) isomer (Problem 14-62). Explain.
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Chapter 14: Problem 14 Organic Chemistry 9
How would you carry out the following synthesis (more than one step is required)? What stereochemical relationship between the ]CO2CH3 group attached to the cyclohexane ring and the ]CHO groups would your synthesis produce? CO2CH3 + ? H CO2CH3 CHOH CHOH
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Chapter 14: Problem 14 Organic Chemistry 9
The double bond of an enamine (alkene 1 amine) is much more nucleophilic than a typical alkene double bond. Assuming that the nitrogen atom in an enamine is sp2-hybridized, draw an orbital picture of an enamine, and explain why the double bond is electron-rich. An enamine C C N R R
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Chapter 14: Problem 14 Organic Chemistry 9
Benzene has an ultraviolet absorption at lmax 5 204 nm, and paratoluidine has lmax 5 235 nm. How do you account for this difference? Benzene (max = 204 nm) p-Toluidine (max = 235 nm) H3C NH2
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Chapter 14: Problem 14 Organic Chemistry 9
Why would medicinal chemists now find it more promising to use PDT photosensitizers based on the phthalocyanine core instead of the porphyrin core? (a) Phthalocyanine is more conjugated and therefore lmax is red-shifted. (b) Phthalocyanine is more conjugated and therefore lmax is blue-shifted (c) Phthalocyanine is aromatic and porphyrins are not. (d) Porphyrins are aromatic and phthalocyanine is not.
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Chapter 14: Problem 14 Organic Chemistry 9
Phthalocyanine in solution absorbs light at wavelengths above 650 nm. What color would you expect it to have? (a) Red (b) Orange (c) Yellow (d) Green-blue
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Chapter 14: Problem 14 Organic Chemistry 9
How many p molecular orbitals are present in the phthalocyanine ring? (a) 19 (b) 38 (c) 18 (d) 36
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Chapter 14: Problem 14 Organic Chemistry 9
An increase in conjugation is correlated with _______ in the energy of the LUMO, _______ in the energy of the HOMO, and _______ in lmax, which results in a _______ . (a) a decrease, an increase, a decrease, red shift (b) a decrease, an increase, an increase, red shift (c) an increase, a decrease, a decrease, red shift (d) an increase, a decrease, an increase, blue shift
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Chapter 14: Problem 14 Organic Chemistry 9
What if no ionic solids were soluble in water? How would this affect the way reactions occur in aqueous solutions?
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the molarity of a solution prepared by dissolving 11.5 g of solid NaOH in enough water to make 1.50 L of solution.
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the molarity of a solution prepared by dissolving 1.56 g of gaseous HCl in enough water to make 26.8 mL of solution.
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Chapter 14: Problem 14 Organic Chemistry 9
Give the concentration of each type of ion in the following solutions: a. 0.50 M Co(NO3)2 b. 1 M Fe(ClO4)3
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the number of moles of Cl2 ions in 1.75 L of 1.0 3 1023 M ZnCl2.
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Chapter 14: Problem 14 Organic Chemistry 9
Typical blood serum is about 0.14 M NaCl. What volume of blood contains 1.0 mg of NaCl?
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Chapter 14: Problem 14 Organic Chemistry 9
To analyze the alcohol content of a certain wine, a chemist needs 1.00 L of an aqueous 0.200-M K2Cr2O7 (potassium dichromate) solution. How much solid K2Cr2O7 must be weighed out to make this solution?
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Chapter 14: Problem 14 Organic Chemistry 9
What volume of 16 M sulfuric acid must be used to prepare 1.5 L of a 0.10-M H2SO4 solution?
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Chapter 14: Problem 14 Organic Chemistry 9
Using the solubility rules in Table 4.1, predict what will happen when the following pairs of solutions are mixed. a. KNO3(aq) and BaCl2(aq) b. Na2SO4(aq) and Pb(NO3)2(aq) c. KOH(aq) and Fe(NO3)3(aq)
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Chapter 14: Problem 14 Organic Chemistry 9
For each of the following reactions, write the formula equation, the complete ionic equation, and the net ionic equation. a. Aqueous potassium chloride is added to aqueous silver nitrate to form a silver chloride precipitate plus aqueous potassium nitrate. b. Aqueous potassium hydroxide is mixed with aqueous iron(III) nitrate to form a precipitate of iron(III) hydroxide and aqueous potassium nitrate.
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Chapter 14: Problem 14 Organic Chemistry 9
What if all ionic solids were soluble in water? How would this affect stoichiometry calculations for reactions in aqueous solution?
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the mass of solid NaCl that must be added to 1.50 L of a 0.100-M AgNO3 solution to precipitate all the Ag1 ions in the form of AgCl.
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Chapter 14: Problem 14 Organic Chemistry 9
When aqueous solutions of Na2SO4 and Pb(NO3)2 are mixed, PbSO4 precipitates. Calculate the mass of PbSO4 formed when 1.25 L of 0.0500 M Pb(NO3)2 and 2.00 L of 0.0250 M Na2SO4 are mixed.
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Chapter 14: Problem 14 Organic Chemistry 9
What volume of a 0.100-M HCl solution is needed to neutralize 25.0 mL of 0.350 M NaOH?
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Chapter 14: Problem 14 Organic Chemistry 9
In a certain experiment, 28.0 mL of 0.250 M HNO3 and 53.0 mL of 0.320 M KOH are mixed. What is the concentration of H1 or OH2 ions in excess after the reaction goes to completion?
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Chapter 14: Problem 14 Organic Chemistry 9
A student carries out an experiment to standardize (determine the exact concentration of) a sodium hydroxide solution. To do this, the student weighs out a 1.3009-g sample of potassium hydrogen phthalate (KHC8H4O4, often abbreviated KHP). KHP (molar mass 204.22 g/mol) has one acidic hydrogen. The student dissolves the KHP in distilled water, adds phenolphthalein as an indicator, and titrates the resulting solution with the sodium hydroxide solution to the phenolphthalein endpoint. The difference between the final and initial buret readings indicates that 41.20 mL of the sodium hydroxide solution is required to react exactly with the 1.3009 g KHP. Calculate the concentration of the sodium hydroxide solution.
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Chapter 14: Problem 14 Organic Chemistry 9
In Example 4.14 you determined the concentration of an aqueous solution of NaOH using phenolphthalein as an indicator. What if you used an indicator for which the endpoint of the titration occurs after the equivalence point? How would this affect your calculated concentration of NaOH?
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Chapter 14: Problem 14 Organic Chemistry 9
If pure vitamin A has \(\lambda_{\max }=325(\varepsilon=50,100)\), what is the vitamin A concentration in a sample whose absorbance at \(325 \mathrm{~nm}\) is \(A=0.735\) in a cell with a pathlength of \(1.00 \mathrm{~cm}\) ?
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Chapter 14: Problem 14 Organic Chemistry 9
What if the oxidation state for oxygen was defined as 21 instead of 22? What effect, if any, would it have on the oxidation state of hydrogen?
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Chapter 14: Problem 14 Organic Chemistry 9
Assign oxidation states to all atoms in the following. a. CO2 b. SF6 c. NO3
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Chapter 14: Problem 14 Organic Chemistry 9
Metallurgy, the process of producing a metal from its ore, always involves oxidation reduction reactions. In the metallurgy of galena (PbS), the principal lead-containing ore, the first step is the conversion of lead sulfide to its oxide (a process called roasting): 2PbS1s2 1 3O2 1g2 h 2PbO1s2 1 2SO2 1g2 The oxide is then treated with carbon monoxide to produce the free metal: PbO1s2 1 CO1g2 h Pb1s2 1 CO2 1g2 For each reaction, identify the atoms that are oxidized and reduced, and specify the oxidizing and reducing agents.
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Chapter 14: Problem 14 Organic Chemistry 9
Dalton believed that atoms were indivisible. Thomson and Rutherford helped to show that this was not true. What if atoms were indivisible? How would this affect the types of reactions you have learned about in this chapter?
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Chapter 14: Problem 14 Organic Chemistry 9
Balance the reaction between solid lead(II) oxide and ammonia gas to produce nitrogen gas, liquid water, and solid lead.
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Chapter 14: Problem 14 Organic Chemistry 9
The (aq) designation listed after a solute indicates the process of hydration. Using KBr(aq) and C2H5OH(aq) as your examples, explain the process of hydration for soluble ionic compounds and for soluble covalent compounds
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Chapter 14: Problem 14 Organic Chemistry 9
Characterize strong electrolytes versus weak electrolytes versus nonelectrolytes. Give examples of each. How do you experimentally determine whether a soluble substance is a strong electrolyte, weak electrolyte, or nonelectrolyte?
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Chapter 14: Problem 14 Organic Chemistry 9
Distinguish between the terms slightly soluble and weak electrolyte.
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Chapter 14: Problem 14 Organic Chemistry 9
Molarity is a conversion factor relating moles of solute in solution to the volume of the solution. How does one use molarity as a conversion factor to convert from moles of solute to volume of solution, and from volume of solution to moles of solute present?
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Chapter 14: Problem 14 Organic Chemistry 9
What is a dilution? What stays constant in a dilution? Explain why the equation M1V1 5 M2V2 works for dilution problems.
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Chapter 14: Problem 14 Organic Chemistry 9
When the following beakers are mixed, draw a molecular-level representation of the product mixture (see Fig. 4.17).
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Chapter 14: Problem 14 Organic Chemistry 9
Differentiate between the formula equation, the complete ionic equation, and the net ionic equation. For each reaction in Question 6, write all three balanced equations.
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Chapter 14: Problem 14 Organic Chemistry 9
What is an acidbase reaction? Strong bases are soluble ionic compounds that contain the hydroxide ion. List the strong bases. When a strong base reacts with an acid, what is always produced? Explain the terms titration, stoichiometric point, neutralization, and standardization.
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Chapter 14: Problem 14 Organic Chemistry 9
Define the terms oxidation, reduction, oxidizing agent, and reducing agent. Given a chemical reaction, how can you tell if it is a redox reaction?
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Chapter 14: Problem 14 Organic Chemistry 9
Consider the steps involved in balancing oxidation reduction reactions by using oxidation states. The key to the oxidation states method is to equalize the electrons lost by the species oxidized with the electrons gained by the species reduced. First of all, how do you recognize what is oxidized and what is reduced? Second, how do you balance the electrons lost with the electrons gained? Once the electrons are balanced, what else is needed to balance the oxidationreduction reaction?
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Chapter 14: Problem 14 Organic Chemistry 9
Assume you have a highly magnified view of a solution of HCl that allows you to see the HCl. Draw this magnified view. If you dropped in a piece of magnesium, the magnesium would disappear and hydrogen gas would be released. Represent this change using symbols for the elements, and write out the balanced equation
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Chapter 14: Problem 14 Organic Chemistry 9
You have a solution of table salt in water. What happens to the salt concentration (increases, decreases, or stays the same) as the solution boils? Draw pictures to explain your answer.
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Chapter 14: Problem 14 Organic Chemistry 9
You have a sugar solution (solution A) with concentration x. You pour one-fourth of this solution into a beaker, and add an equivalent volume of water (solution B). a. What is the ratio of sugar in solutions A and B? b. Compare the volumes of solutions A and B. c. What is the ratio of the concentrations of sugar in solutions A and B?
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Chapter 14: Problem 14 Organic Chemistry 9
You add an aqueous solution of lead nitrate to an aqueous solution of potassium iodide. Draw highly magnified views of each solution individually, and the mixed solution, including any product that forms. Write the balanced equation for the reaction
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Chapter 14: Problem 14 Organic Chemistry 9
Order the following molecules from lowest to highest oxidation state of the nitrogen atom: HNO3, NH4Cl, N2O, NO2, NaNO2.
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Chapter 14: Problem 14 Organic Chemistry 9
Why is it that when something gains electrons, it is said to be reduced? What is being reduced?
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Chapter 14: Problem 14 Organic Chemistry 9
Consider separate aqueous solutions of HCl and H2SO4 with the same molar concentrations. You wish to neutralize an aqueous solution of NaOH. For which acid solution would you need to add more volume (in milliliters) to neutralize the base? a. the HCl solution b. the H2SO4 solution c. You need to know the acid concentrations to answer this question. d. You need to know the volume and concentration of the NaOH solution to answer this question. e. c and d Explain
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Chapter 14: Problem 14 Organic Chemistry 9
Draw molecular-level pictures to differentiate between concentrated and dilute solutions.
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Chapter 14: Problem 14 Organic Chemistry 9
You need to make 150.0 mL of a 0.10-M NaCl solution. You have solid NaCl, and your lab partner has a 2.5-M NaCl solution. Explain how you each make the 0.10-M NaCl solution.
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Chapter 14: Problem 14 Organic Chemistry 9
The exposed electrodes of a light bulb are placed in a solution of H2SO4 in an electrical circuit such that the light bulb is glowing. You add a dilute salt solution, and the bulb dims. Which of the following could be the salt in the solution? a. Ba(NO3)2 c. K2SO4 b. NaNO3 d. Ca(NO3)2 Justify your choices. For those you did not choose, explain why they are incorrect.
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Chapter 14: Problem 14 Organic Chemistry 9
You have two solutions of chemical A. To determine which has the highest concentration of A (molarity), which of the following must you know (there may be more than one answer)? a. the mass in grams of A in each solution b. the molar mass of A c. the volume of water added to each solution d. the total volume of the solution Explain
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following must be known to calculate the molarity of a salt solution (there may be more than one answer)? a. the mass of salt added b. the molar mass of the salt c. the volume of water added d. the total volume of the solution Explain
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Chapter 14: Problem 14 Organic Chemistry 9
Differentiate between what happens when the following are added to water. a. polar solute versus nonpolar solute b. KF versus C6H12O6 c. RbCl versus AgCl d. HNO3 versus CO
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Chapter 14: Problem 14 Organic Chemistry 9
A typical solution used in general chemistry laboratories is 3.0 M HCl. Describe, in detail, the composition of 2.0 L of a 3.0-M HCl solution. How would 2.0 L of a 3.0-M HC2H3O2 solution differ from the same quantity of the HCl solution?
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following statements is(are) true? For the false statements, correct them. a. A concentrated solution in water will always contain a strong or weak electrolyte. b. A strong electrolyte will break up into ions when dissolved in water. c. An acid is a strong electrolyte. d. All ionic compounds are strong electrolytes in water
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Chapter 14: Problem 14 Organic Chemistry 9
A student wants to prepare 1.00 L of a 1.00-M solution of NaOH (molar mass 5 40.00 g/mol). If solid NaOH is available, how would the student prepare this solution? If 2.00 M NaOH is available, how would the student prepare the solution? To help ensure three significant figures in the NaOH molarity, to how many significant figures should the volumes and mass be determined?
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Chapter 14: Problem 14 Organic Chemistry 9
List the formulas of three soluble bromide salts and three insoluble bromide salts. Do the same exercise for sulfate salts, hydroxide salts, and phosphate salts (list three soluble salts and three insoluble salts). List the formulas for six insoluble Pb21 salts and one soluble Pb21 salt
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Chapter 14: Problem 14 Organic Chemistry 9
When 1.0 mole of solid lead nitrate is added to 2.0 moles of aqueous potassium iodide, a yellow precipitate forms. After the precipitate settles to the bottom, does the solution above the precipitate conduct electricity? Explain. Write the complete ionic equation to help you answer this question.
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Chapter 14: Problem 14 Organic Chemistry 9
What is an acid and what is a base? An acidbase reaction is sometimes called a proton-transfer reaction. Explain.
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Chapter 14: Problem 14 Organic Chemistry 9
A student had 1.00 L of a 1.00-M acid solution. Much to the surprise of the student, it took 2.00 L of 1.00 M NaOH solution to react completely with the acid. Explain why it took twice as much NaOH to react with all of the acid. In a different experiment, a student had 10.0 mL of 0.020 M HCl. Again, much to the surprise of the student, it took only 5.00 mL of 0.020 M strong base to react completely with the HCl. Explain why it took only half as much strong base to react with all of the HCl.
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Chapter 14: Problem 14 Organic Chemistry 9
Differentiate between the following terms. a. species reduced versus the reducing agent b. species oxidized versus the oxidizing agent c. oxidation state versus actual charge
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Chapter 14: Problem 14 Organic Chemistry 9
How does one balance redox reactions by the oxidation states method?
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Chapter 14: Problem 14 Organic Chemistry 9
Show how each of the following strong electrolytes breaks up into its component ions upon dissolving in water by drawing molecular-level pictures. a. NaBr f. FeSO4 b. MgCl2 g. KMnO4 c. Al(NO3)3 h. HClO4 d. (NH4)2SO4 i. NH4C2H3O2 (ammonium acetate) e. NaOH
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Chapter 14: Problem 14 Organic Chemistry 9
Match each name below with the following microscopic pictures of that compound in aqueous solution. + + + + + + + 2+ 2+ 2+ 2+ 2 2 2 2 i. ii. iii. iv. a. barium nitrate c. potassium carbonate b. sodium chloride d. magnesium sulfate Which picture best represents HNO3(aq)? Why arent any of the pictures a good representation of HC2H3O2(aq)?
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Chapter 14: Problem 14 Organic Chemistry 9
Calcium chloride is a strong electrolyte and is used to salt streets in the winter to melt ice and snow. Write a reaction to show how this substance breaks apart when it dissolves in water.
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Chapter 14: Problem 14 Organic Chemistry 9
Commercial cold packs and hot packs are available for treating athletic injuries. Both types contain a pouch of water and a dry chemical. When the pack is struck, the pouch of water breaks, dissolving the chemical, and the solution becomes either hot or cold. Many hot packs use magnesium sulfate, and many cold packs use ammonium nitrate. Write reactions to show how these strong electrolytes break apart when they dissolve in water.
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the molarity of each of these solutions. a. A 5.623-g sample of NaHCO3 is dissolved in enough water to make 250.0 mL of solution. b. A 184.6-mg sample of K2Cr2O7 is dissolved in enough water to make 500.0 mL of solution. c. A 0.1025-g sample of copper metal is dissolved in 35 mL of concentrated HNO3 to form Cu21 ions and then water is added to make a total volume of 200.0 mL. (Calculate the molarity of Cu21.)
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Chapter 14: Problem 14 Organic Chemistry 9
A solution of ethanol (C2H5OH) in water is prepared by dissolving 75.0 mL of ethanol (density 5 0.79 g/cm3 ) in enough water to make 250.0 mL of solution. What is the molarity of the ethanol in this solution?
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the concentration of all ions present in each of the following solutions of strong electrolytes. a. 0.100 mole of Ca(NO3)2 in 100.0 mL of solution b. 2.5 moles of Na2SO4 in 1.25 L of solution c. 5.00 g of NH4Cl in 500.0 mL of solution d. 1.00 g K3PO4 in 250.0 mL of solution
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the concentration of all ions present in each of the following solutions of strong electrolytes. a. 0.0200 mole of sodium phosphate in 10.0 mL of solution b. 0.300 mole of barium nitrate in 600.0 mL of solution c. 1.00 g of potassium chloride in 0.500 L of solution d. 132 g of ammonium sulfate in 1.50 L of solution
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following solutions of strong electrolytes contains the largest number of moles of chloride ions: 100.0 mL of 0.30 M AlCl3, 50.0 mL of 0.60 M MgCl2, or 200.0 mL of 0.40 M NaCl?
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Chapter 14: Problem 14 Organic Chemistry 9
Which of the following solutions of strong electrolytes contains the largest number of ions: 100.0 mL of 0.100 M NaOH, 50.0 mL of 0.200 M BaCl2, or 75.0 mL of 0.150 M Na3PO4?
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Chapter 14: Problem 14 Organic Chemistry 9
What mass of NaOH is contained in 250.0 mL of a 0.400 M sodium hydroxide solution?
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Chapter 14: Problem 14 Organic Chemistry 9
If 10. g of AgNO3 is available, what volume of 0.25 M AgNO3 solution can be prepared?
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Chapter 14: Problem 14 Organic Chemistry 9
Describe how you would prepare 2.00 L of each of the following solutions. a. 0.250 M NaOH from solid NaOH b. 0.250 M NaOH from 1.00 M NaOH stock solution c. 0.100 M K2CrO4 from solid K2CrO4 d. 0.100 M K2CrO4 from 1.75 M K2CrO4 stock solution
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Chapter 14: Problem 14 Organic Chemistry 9
How would you prepare 1.00 L of a 0.50-M solution of each of the following? a. H2SO4 from concentrated (18 M) sulfuric acid b. HCl from concentrated (12 M) reagent c. NiCl2 from the salt NiCl2 ? 6H2O d. HNO3 from concentrated (16 M) reagent e. Sodium carbonate from the pure solid
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Chapter 14: Problem 14 Organic Chemistry 9
A solution is prepared by dissolving 10.8 g ammonium sulfate in enough water to make 100.0 mL of stock solution. A 10.00-mL sample of this stock solution is added to 50.00 mL of water. Calculate the concentration of ammonium ions and sulfate ions in the final solution.
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Chapter 14: Problem 14 Organic Chemistry 9
A solution was prepared by mixing 50.00 mL of 0.100 M HNO3 and 100.00 mL of 0.200 M HNO3. Calculate the molarity of the final solution of nitric acid.
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Chapter 14: Problem 14 Organic Chemistry 9
Calculate the sodium ion concentration when 70.0 mL of 3.0 M sodium carbonate is added to 30.0 mL of 1.0 M sodium bicarbonate.
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Chapter 14: Problem 14 Organic Chemistry 9
Suppose 50.0 mL of 0.250 M CoCl2 solution is added to 25.0 mL of 0.350 M NiCl2 solution. Calculate the concentration, in moles per liter, of each of the ions present after mixing. Assume that the volumes are additive.
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Chapter 14: Problem 14 Organic Chemistry 9
A standard solution is prepared for the analysis of fluoxymesterone (C20H29FO3), an anabolic steroid. A stock solution is first prepared by dissolving 10.0 mg of fluoxymesterone in enough water to give a total volume of 500.0 mL. A 100.0-mL aliquot (portion) of this solution is diluted to a final volume of 100.0 mL. Calculate the concentration of the final solution in terms of molarity
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Chapter 14: Problem 14 Organic Chemistry 9
A stock solution containing Mn21 ions was prepared by dissolving 1.584 g pure manganese metal in nitric acid and diluting to a final volume of 1.000 L. The following solutions were then prepared by dilution: For solution A, 50.00 mL of stock solution was diluted to 1000.0 mL. For solution B, 10.00 mL of solution A was diluted to 250.0 mL. For solution C, 10.00 mL of solution B was diluted to 500.0 mL. Calculate the concentrations of the stock solution and solutions A, B, and C.
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Chapter 14: Problem 14 Organic Chemistry 9
On the basis of the general solubility rules given in Table 4.1, predict which of the following substances are likely to be soluble in water. a. aluminum nitrate b. magnesium chloride c. rubidium sulfate d. nickel(II) hydroxide e. lead(II) sulfide f. magnesium hydroxide g. iron(III) phosphate
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Chapter 14: Problem 14 Organic Chemistry 9
On the basis of the general solubility rules given in Table 4.1, predict which of the following substances are likely to be soluble in water. a. zinc chloride b. lead(II) nitrate c. lead(II) sulfate d. sodium iodide e. cobalt(III) sulfide f. chromium(III) hydroxide g. magnesium carbonate h. ammonium carbonate
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Chapter 14: Problem 14 Organic Chemistry 9
When the following solutions are mixed together, what precipitate (if any) will form? a. FeSO4(aq) 1 KCl(aq) b. Al(NO3)3(aq) 1 Ba(OH)2(aq) c. CaCl2(aq) 1 Na2SO4(aq) d. K2S(aq) 1 Ni(NO3)2(aq)
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Chapter 14: Problem 14 Organic Chemistry 9
When the following solutions are mixed together, what precipitate (if any) will form? a. Hg2(NO3)2(aq) 1 CuSO4(aq) b. Ni(NO3)2(aq) 1 CaCl2(aq) c. K2CO3(aq) 1 MgI2(aq) d. Na2CrO4(aq) 1 AlBr3(aq)
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Chapter 14: Problem 14 Organic Chemistry 9
For the reactions in Exercise 45, write the balanced formula equation, complete ionic equation, and net ionic equation. If no precipitate forms, write No reaction.
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Chapter 14: Problem 14 Organic Chemistry 9
For the reactions in Exercise 46, write the balanced formula equation, complete ionic equation, and net ionic equation. If no precipitate forms, write No reaction.
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Chapter 14: Problem 14 Organic Chemistry 9
Write the balanced formula and net ionic equation for the reaction that occurs when the contents of the two beakers are added together. What colors represent the spectator ions in each reaction? + Cu2+ SO4 2 Na+ S2 a. + Co2+ Cl Na+ OH b. + Ag+ NO3 K+ I
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Chapter 14: Problem 14 Organic Chemistry 9
Give an example how each of the following insoluble ionic compounds could be produced using a precipitation reaction. Write the balanced formula equation for each reaction. a. Fe(OH)3(s) c. PbSO4(s) b. Hg2Cl2(s) d. BaCrO4(s)
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Chapter 14: Problem 14 Organic Chemistry 9
Write net ionic equations for the reaction, if any, that occurs when aqueous solutions of the following are mixed. a. ammonium sulfate and barium nitrate b. lead(II) nitrate and sodium chloride c. sodium phosphate and potassium nitrate d. sodium bromide and rubidium chloride e. copper(II) chloride and sodium hydroxide
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Chapter 14: Problem 14 Organic Chemistry 9
Write net ionic equations for the reaction, if any, that occurs when aqueous solutions of the following are mixed. a. chromium(III) chloride and sodium hydroxide b. silver nitrate and ammonium carbonate c. copper(II) sulfate and mercury(I) nitrate d. strontium nitrate and potassium iodide
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Chapter 14: Problem 14 Organic Chemistry 9
Separate samples of a solution of an unknown soluble ionic compound are treated with KCl, Na2SO4, and NaOH. A precipitate forms only when Na2SO4 is added. Which cations could be present in the unknown soluble ionic compound?
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Chapter 14: Problem 14 Organic Chemistry 9
A sample may contain any or all of the following ions: Hg2 21, Ba21, and Mn21. a. No precipitate formed when an aqueous solution of NaCl was added to the sample solution. b. No precipitate formed when an aqueous solution of Na2SO4 was added to the sample solution. c. A precipitate formed when the sample solution was made basic with NaOH. Which ion or ions are present in the sample solution?
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Chapter 14: Problem 14 Organic Chemistry 9
What mass of Na2CrO4 is required to precipitate all of the silver ions from 75.0 mL of a 0.100-M solution of AgNO3?
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Chapter 14: Problem 14 Organic Chemistry 9
What volume of 0.100 M Na3PO4 is required to precipitate all the lead(II) ions from 150.0 mL of 0.250 M Pb(NO3)2?
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Chapter 14: Problem 14 Organic Chemistry 9
What mass of solid aluminum hydroxide can be produced when 50.0 mL of 0.200 M Al(NO3)3 is added to 200.0 mL of 0.100 M KOH
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