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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

(Use models to solve this problem.) (a) Write a conformational structure for the most stable conformation of trans-1, 2-iethylcyclohexane and write its mirror image. (b) Are these two molecules
Which atom is the chirality center of (a) limonene and (b) of thalidomide?
(Use models to solve this problem.) (a) Write a conformational structure for the most stable conformation of trans- 1, 4-diethylcyclohexane and for its mirror image. (b) Are these structures
Write conformational structures for all of the stereoisomers of 1,3-diethylcyclohexane. Label pairs of enantiomers and meso compounds if they exist.
Tartaric acid [HO2CCH(OH)CH(OH)CO2H] was an important compound in the history of stereochemistry. Two naturally occurring forms of tartaric acid are optically inactive. One optically inactive form
(a) An aqueous solution of pure stereoisomer X of concentration 0.10 g mL-1 had an observed rotation of -300 in a 1.0-dm tube at 589.6 nm (the sodium D line) and 25oC. What do you calculate its [a]D
Unknown Y has a molecular formula of C3H6O2. It contains one functional group that absorbs infrared radiation in the 3200-3550-cm-1 region (when studied as a pure liquid; i.e., "neat"), and it has no
Which atoms in each of the following molecules are chirality centers?(a)(b) (c) (d)
Write three-dimensional formulas and designate a plane of symmetry for all of the achiral molecules in Practice Problem 5.4. (In order to be able to designate a plane of symmetry you may need to
Write the enantiomeric forms of bromochlorofluoromethane and assign each enantiomer its correct (R) or (S) designation.
The relative rates of ethanolysis of four primary alkyl halides are as follows: CH3CH2Br, 1.0; CH3CH2CH2Br, 0.28; (CH3)2CHCH2Br, 0.030; (CH3)3CCH2Br, 0.00000042. (a) Is each of these reactions likely
Classify the following solvents as being protic or aprotic: formic acid, HCO2H; acetone, CH3COCH3; acetonitrile, CH3C≡N; formamide, HCONH2; sulfur dioxide, SO2; ammonia, NH3; trimethylamine,
Would you expect the reaction of propyl bromide with sodium cyanide (NaCN), that is, CH3CH2CH2Br + NaCN → CH3CH2CH2CN + NaBr to occur faster in DMF or in ethanol? Explain your answer.
When tert-butyl bromide undergoes solvolysis in a mixture of methanol and water, the rate of solvolysis (measured by the rate at which bromide ions form in the mixture) increases when the percentage
List the following compounds in order of decreasing reactivity toward CH3O- in an SN2 reaction carried out in CH3OH: CH3F, CH3Cl, CH3Br, CH3I, CH3OSO2CF3, 14CH3OH.
Starting with (S)-2-bromobutane, outline syntheses of each of the following compounds:(a)(b) (c) (d)
Which alkyl halide would you expect to react more rapidly by an SN2 mechanism? Explain your answer.(a)(b) (c) (d) (e)
Which SN2 reaction of each pair would you expect to take place more rapidly in a protic solvent?(a) (1)Or (2) (b) (1) Or (2) (c) (1) Or (2) (d) (1) Or (2)
Which SN1 reaction of each pair would you expect to take place more rapidly? Explain your answer.(a) (1)Or (2) (b) (1) Or (2) (c) (1) Or (2) (d) (1) Or (2) (e) (1) Or (2)
Show how you might use a nucleophilic substitution reaction of 1-bromopropane to synthesize each of the following compounds. (You may use any other compounds that are necessary.)(a)(b)
With methyl, ethyl, or cyclopentyl halides as your organic starting materials and using any needed solvents or inorganic reagents, outline syntheses of each of the following. More than one step may
Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an
Your task is to prepare styrene by one of the following reactions. Which reaction would you choose to give the better yield of styrene? Explain your answer.(1)Styrene Or (2) Styrene
Your task is to prepare isopropyl methyl ether by one of the following reactions. Which reaction would give the better yield? Explain your answer.(1)Isopropyl methyl ether Or (2) Isopropyl methyl
Starting with an appropriate alkyl halide and using any other needed reagents, outline syntheses of each of the following. When alternative possibilities exist for a synthesis, you should be careful
Which product (or products) would you expect to obtain from each of the following reactions? In each part give the mechanism (SN1, SN2, E1, or E2) by which each product is formed and predict the
Write the following as net ionic equations and designate the nucleophile, substrate, and leaving group in each reaction:(a) CH3I + CH3CH2ONa †’ CH3OCH2CH3 + NaI(b) NaI + CH3CH2Br
Write conformational structures for the substitution products of the following deuterium-labeled compounds:(a)(b) (c) (d)
Although ethyl bromide and isobutyl bromide are both primary halides, ethyl bromide undergoes SN2 reactions more than 10 times faster than isobutyl bromide does. When each compound is treated with a
Consider the reaction of I- with CH3CH2Cl. (a) Would you expect the reaction to be SN1 or SN2? The rate constant for the reaction at 60oC is 5 × 10-5 L mol-1 s-1. (b) What is the reaction rate if
Which reagent in each pair listed here would be the more reactive nucleophile in a polar aprotic solvent? (a) CH3H or CH3NH2 (b) CH3O- or CH3CO2- (-OAc) (c) CH3SH or CH3OH (d) (C6H5)3N or
Write mechanisms that account for the products of the following reactions:(a)(b)
Draw a three-dimensional representation for the transition state structure in the SN2 reaction of N≡C:- (cyanide anion) with bromoethane, showing all nonbonding electron pairs and full or partial
Many SN2 reactions of alkyl chlorides and alkyl bromides are catalyzed by the addition of sodium or potassium iodide. For example, the hydrolysis of methyl bromide takes place much faster in the
Explain the following observations: When tert-butyl bromide is treated with sodium methoxide in a mixture of methanol and water, the rate of formation of tert-butyl alcohol and tert-butyl methyl
(a) Consider the general problem of converting a tertiary alkyl halide to an alkene, for example, the conversion of tert-butyl chloride to 2-methylpropene. What experimental conditions would you
1-Bromobicyclo [2.2.1] heptane is extremely unreactive in either SN2 or SN1 reactions. Provide explanations for this behavior.
Draw a hypothetical free-energy diagram for the SN2 reaction of iodide anion with 1-chlorobutane. Label the diagram as in Fig. 6.4, and assume it is exergonic but without specific values for
When ethyl bromide reacts with potassium cyanide in methanol, the major product is CH3CH2CN. Some CH3CH2NC is formed as well, however. Write Lewis structures for the cyanide ion and for both products
Give structures for the products of each of the following reactions:(a)(b) (c) (d) (e)
When tert-butyl bromide undergoes SN1 hydrolysis, adding a "common ion" (e.g., NaBr) to the aqueous solution has no effect on the rate. On the other hand, when (C6H5)2CHBr undergoes SN1 hydrolysis,
When the alkyl bromides (listed here) were subjected to hydrolysis in a mixture of ethanol and water (80% EtOH/20% H2O) at 55oC, the rates of the reaction showed the following order: (CH3)3CBr >
The reaction of 1o alkyl halides with nitrite salts produces both RNO2 and RONO. Account for this behavior.
What would be the effect of increasing solvent polarity on the rate of each of the following nucleophilic substitution reactions? (a) Nu: + R-L → R-Nu+ + :L (b) R-L+ → R+ + :L
Competition experiments are those in which two reactants at the same concentration (or one reactant with two reactive sites) compete for a reagent. Predict the major product resulting from each of
In contrast to SN2 reactions, SN1 reactions show relatively little nucleophile selectivity. That is, when more than one nucleophile is present in the reaction medium, SN1 reactions show only a slight
The reaction of chloroethane with water in the gas phase to produce ethanol and hydrogen chloride has ∆Ho = +26.6 kJ mol-1 and ∆So = +4.81 J K-1 mol-1 at 25oC. (a) Which of these terms, if
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
Using chair conformational structures (Section 4.11), show the nucleophilic substitution reaction that would take place when trans-1-bromo-4-tert-butylcyclohexane reacts with iodide ion. (Show the
The phenomenon of configuration inversion in a chemical reaction was discovered in 1896 by Paul Walden (Section 6.6). Walden's proof of configuration inversion was based on the following cycle:(a)
(R)-(3-Chloro-2-methylpropyl) methyl ether (A) on reaction with azide ion (N3-) in aqueous ethanol gives (S)-(3-azido-2-methylpropyl) methyl ether (B). Compound A has the structure
Predict the structure of the product of this reaction:The product has no infrared absorption in the 1620-1680-cm-1 region.
Cis-4-Bromocyclohexanol racemic C6H10O (compound C) Compound C has infrared absorption in the 1620-1680-cm-1 and in the 3590-3650-cm-1 regions. Draw and label the (R) and (S) enantiomers
1-Bromo [2.2.1] bicycloheptane is unreactive toward both SN2 and SN1 reactions. Open the computer molecular model at the book's website titled "1-Bromo [2.2.1] bicycloheptane" and examine the
Open the computer molecular model titled "1-Bromo [2.2.1] bicycloheptane LUMO" at the book's website for the lowest unoccupied molecular orbital (LUMO) of this compound. Where is the lobe of the LUMO
In the previous problem and the associated molecular model at the book's website, you considered the role of HOMOs and LUMOs in an SN2 reaction. (a) What is the LUMO in an SN1 reaction and in what
SN2 reactions that involve breaking a bond to a chirality center can be used to relate configurations of molecules because the stereochemistry of the reaction is known.(a) Illustrate how this is true
Keeping in mind that carbocations have a trigonal planar structure,(a) Write a structure for the carbocation intermediate(b) Write structures for the alcohol (or alcohols) that you would expect from
What product(s) would you expect from the methanolysis of the iodocyclohexane derivative given as the reactant in Practice Problem 6.8?In Problem 6.8
Using the (E)-(Z) designation [and in parts (e) and (f) the (R)-(S) designation as well] give IUPAC names for each of the following:(a)(b) (c) (d) (e) (f)
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-
(a) When cis-1-bromo-2-methylcyclohexane undergoes an E2 reaction, two products (cycloalkenes) are formed. What are these two cycloalkenes, and which would you expect to be the major product? Write
Dehydration of 2-propanol occurs in 14 M H2SO4 at 100oC. (a) Using curved arrows, write all steps in a mechanism for the dehydration. (b) Explain the essential role performed in alcohol dehydrations
Rank the following alcohols in order of increasing ease of acid-catalyzed dehydration.
Acid-catalyzed dehydration of neopentyl alcohol, (CH3)3CCH2OH, yields 2-methyl-2- butene as the major product. Outline a mechanism showing all steps in its formation.
Acid-catalyzed dehydration of either 2-methyl-1-butanol or 3-methyl-1-butanol gives 2-methyl-2-butene as the major product. Write plausible mechanisms that explain these results.
When the compound called isoborneol is heated with 9 M sulfuric acid, the product of the reaction is the compound called camphene and not bornylene, as one might expect. Using models to assist you,
Predict the products of the following acid-base reactions. If the equilibrium would not result in the formation of appreciable amounts of products, you should so indicate. In each case label the
Show how you might synthesize ethynylbenzene from methyl phenyl ketone.
Outline all steps in a synthesis of propyne from each of the following: (a) CH3COCH3 (b) CH3CH2CHBr2 (c) CH3CHBrCH2Br (d) CH3CH==CH2
Rank the following cycloalkenes in order of increasing stability.
Your goal is to synthesize 4, 4-dimethyl-2-pentyne. You have a choice of beginning withany of the following reagents:Assume that you also have available sodium amide and liquid ammonia. Outline the
Write the structure of compound A, used in this synthesis of the perfume ingredient (Z)-jasmone.
How would you convert 2-nonyne into (E)-2-nonene?
Referring to the retrosynthetic analysis for 2-methylhexane in this section, write reactions for those synthesis routes that are feasible
(a) Devise retrosynthetic schemes for all conceivable alkynide anion alkylation syntheses insect pheromones undecane and 2-methylheptadecane.(b) Write reactions for two feasible syntheses of each
Each of the following names is incorrect. Give the correct name and explain your reasoning. (a) trans-3-Pentene (b) 1, 1-Dimethylethene (c) 2-Methylcyclohexene (d) 4-Methylcyclobutene (e)
Write a structural formula for each of the following: (a) 3-Methylcyclobutene (b) 1-Methylcyclopentene (c) 2, 3-Dimethyl-2-pentene (d) (Z)-3-Hexene (e) (E)-2-Pentene (f) 3, 3, 3-Tribromopropene (g)
Write three-dimensional formulas for and give names using (R)-(S) and (E)-(Z) designations for the isomers of: (a) 4-Bromo-2-hexene (b) 3-Chloro-1, 4-hexadiene (c) 2, 4-Dichloro-2-pentene (d)
Give the IUPAC names for each of the following:(a)(b) (c) (d) (e) (f)
Heats of hydrogenation of three alkenes are as follows: 2-methyl-1-butene (-119 kJ mol-1) 3-methyl-1-butene (-127 kJ mol-1) 2-methyl-2-butene (-113 kJ mol-1) (a) Write the structure of each alkene
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
Outline a synthesis of cyclopentene from each of the following: (a) Bromocyclopentane (b) Cyclopentanol
Starting with ethyne, outline syntheses of each of the following. You may use any other needed reagents, and you need not show the synthesis of compounds prepared in earlier parts of this problem.(a)
Starting with 1-methylcyclohexene and using any other needed reagents, outline a synthesis of the following deuterium- labeled compound:
Outline a synthesis of phenylethyne from each of the following:(a)(b) (c) (d)
Write a three-dimensional representation for the transition state structure leading to formation of 2-methyl-2-butene from reaction of 2-bromo-2-methylbutane with sodium ethoxide.
When trans-2-methylcyclohexanol (see the following reaction) is subjected to acid-catalyzed dehydration, the major product is 1-methylcyclohexene:However, when trans-1-bromo-2-methylcyclohexane is
Write structural formulas for all the products that would be obtained when each of the following alkyl halides is heated with sodium ethoxide in ethanol. When more than one product results, you
Write structural formulas for all the products that would be obtained when each of the following alkyl halides is heated with potassium tert-butoxide in tert-butyl alcohol. When more than one product
Starting with an appropriate alkyl halide and base, outline syntheses that would yield each of the following alkenes as the major (or only) product:(a)(b) (c) (d) (e)
Predict the more stable alkene of each pair: (a) 2-methyl-2-pentene or 2,3-dimethyl- 2-butene; (b) Cis-3-hexene or trans-3-hexene; (c) 1-hexene or cis-3-hexene; (d) Trans-2- hexene or
Arrange the following alcohols in order of their reactivity toward acid-catalyzed dehydration (with the most reactive first): 1-Pentanol 2-Methyl-2-butanol 3-Methyl-2-butanol
Give the products that would be formed when each of the following alcohols is subjected to acid-catalyzed dehydration. If more than one product would be formed, designate the alkene that would be the
1-Bromobicyclo [2.2.1] heptane does not undergo elimination (below) when heated with a base. Explain this failure to react. (Construction of molecular models may help.)
When the deuterium-labeled compound shown at right is subjected to dehydrohalogenation using sodium ethoxide in ethanol, the only alkene product is 3-methylcyclohexene. (The product contains no
Provide a mechanistic explanation for each of the following reactions:(a)(b) (c) (d)
Caryophyllene, a compound found in oil of cloves, has the molecular formula C15H24 and has no triple bonds. Reaction of caryophyllene with an excess of hydrogen in the presence of a platinum catalyst
Squalene, an important intermediate in the biosynthesis of steroids, has the molecular formula C30H50 and has no triple bonds.(a) What is the index of hydrogen deficiency of squalene?(b) Squalene
Compounds I and J both have the molecular formula C7H14. Compounds I and J are both optically active and both rotate plane-polarized light in the same direction. On catalytic hydrogenation I and J

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