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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Give IUPAC names for the following compounds:
Draw structures corresponding to the following IUPAC names:(a) 2-Methyl-1, 5-hexadiene(b) 3-Ethyl-2, 2-dimethyl-3-heptene(c) 2, 3, 3-Trimethyl-1, 4, 6-octatriene(d) 3, 4-Diisopropyl-2,
Name the following cycloalkenes:
Which of the following compounds can exist as pairs of cis—Trans isomers? Draw each cis—Trans pair, and indicate the geometry of each isomer.(a) CH3CH = CH2(b) (CH3)2C = CHCH3(c) CH3CH2CH =
Name the following alkenes, including the cis or Tran?s designation:
Which member in each of the following sets has higher priority?(a) —H or —Br(b) —C1 or —Br(c) —CH3 or —CH2CH3(d) —NH2 or —OH(e) —CH2OH or —CH3(f) —CH2OH or ─CH = O
Rank the following sets of substituents in order of Cahn-In-gold Prelog priorities:(a) —CH3, —0H, —H, —C1(b) —CH3, —CH2CH3, —CH = CH2, —CH2OH(c) —CO2H, —CH2OH, —C = N,
Assign F or Z configuration to the following alkenes:
Assign stereochemistry (E or Z) to the double bond in the following compound, and convert the drawing into a skeletal structure (red0):
Name the following alkenes, and tell which compound in each pair is more stable
Predict the products of the following reactions:
What alkenes would you start with to prepare the following alkylhalides?
Show the structures of the carbocation intermediates you would expect in the following reactions:
Draw a skeletal structure of the following carbocation. Identify it as primary, secondary, or tertiary, and identify the hydrogen atoms that have the proper orientation for hyper conjugation in the
What about the second step in the electrophilic addition of IIC1 to an alkene—the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the
On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to yield 1-bromo-1-ethylcyclohcxane. Using curved arrows, propose a mechanism to account for this result.
Name the following alkenes, and convert each drawing into a skeletal structure:
Assign stereochemistry (E or Z) to the double bonds in each of the following compounds, and convert each drawing into a skeletal structure (red ? 0, yellow-green = C1):
The following carbocation is an intermediate in the electrophilic addition reaction of 1-ICI with two different alkenes. Identify both, and tell which C?IT bonds in the carbocation are aligned for
Calculate the degree of unsaturation in the following formulas, and draw five possible structures for each:(a) C10H16(b) C8H8O(c) C7H10C12(d) C10H16O2(e) C5H9NO2(f) C8H10C1NO
How many types of hydrogen does each of the following compounds have?(a) C8H? O2, has two rings and one double bond(b) C7H? N, has two double bonds(c) C911? NO, have one ring and three double bonds
Loratadine, marketed as an antiallergy medication under the name Claritin, has four rings, eight double bonds, and the formula C22H? C1N2O2. How many types of hydrogen does loratadine have?
Name the following alkenes:
Ocimene is a triene found in the essential oils or many plants. What is its IUPAC name, including stereo chemistry?
? - Farnesene is a constituent of the natural wax found on apples. What is its IUPAC name, including stereo chemistry?
Draw structures corresponding to the following systematic names:(a) (4E)-2, 4-Dimethyl- 1, 4-hexadiene(b) cis-3, 3-Dimethyl-4-propyl-1, 5-octadicne(c) 4-Methyl-1, 2-pentadiene(d) (3E, 5Z)-2,
Menthene, a hydrocarbon found in mint plants, has the systematic name 1-isopropyl-4-methylcyclohexene. Draw its structure.
Draw and name the 6 pentene isomers, C5H10, including E, Z isomers.
Draw and name the 17 hexene isomers, C6H2, including E, Z isomers.
Trans-2-Buterw is more stable than cic-2-hutene by only 4kJ/mol, but trans-2, 2, 5; 5-tetramethyl-3-hexene is more stable than its cis isomer by 3kJ/mol. Explain.
Cyclodecene can exist in both cis and Tran’s forms, but cyclohexene cannot. Explain. (Making molecular models is helpful.)
Normally, a Tran’s alkene is more stable than its cis isomer Trans-Cyclooctene, however, is less stable than cis-Cyclooctene by 38.5kJ/mol. Explain.
Trans-Cyclooctene is less stable than cis-Cyclooctene by 38.5kJ/mol, but Tran’s cyclononene is less stable than cis-cyclononene by only 12.2kJ/mol. Explain.
Allene (1, 2-propadiene), H2C = C = CH2, has two adjacent double bonds. What kind of hybridization must the central carbon have? Sketch the bonding π orbital’s in allene. What shape do you predict
The heat of hydrogenation for allene (Problem 6.37) to yield propane is —295kJ/mol, and the heat of hydrogenation for a typical monosubstituted alkene such as propene is —126kJ/mol. Is allene
Predict the major product in each of the following reactions:
Predict the major product from addition of HBr to each of the following alkenes:
Rank the following sets of substituents in order of priority according to the Cahn-lngold?Prelog sequence rules:
An Assign E or Z configuration to each of the following alkenes:
Name the following cycloalkenes:
Fucoserraten, ectocarpen, and multifidene are sex pheromones produced by marine brown algae. What are their systematic names? (The latter two are a bit difficult; make your best guess.)
Which of the following E, Z designations are correct, and which are in correct?
A tert-l3utyI esters [RCO2C (CH3)3] are converted into carboxylic acids (RCO2H) by reaction with trifluoroacetic acid, a reaction useful in protein synthesis (Section 26.7). Assign E, Z designation
Each of the following carbocations can rearrange to a more stable ion. Propose structures for the likely rearrangement products.
Addition of HCI to 1-isopropylcyclohexene yields a rearranged product. Propose a mechanism, showing the structures of the intermediates and using curved arrows to indicate electron flow in each step.
Addition of HCI to 1-isopropcnyl-1-methylcyclopcntane yields 1-chloro-1, 2, 2- trimethylcyclohexane. Propose a mechanism, showing the structures of the intermediates and using curved arrows to
Vinylcyclopropane reacts with HBr to yield a rearranged alkyl bromide. Follow the flow of electrons as represented by the curved arrows, show the structure of the carbocation intermediate in
Calculate the degree of unsaturation in each of the following formulas:(a) Cholesterol, C27H46O(b) DDT, C14H9C15(c) Prostaglandin E1, C20H34O5(d) Caffeine, C8H10N4O2(e) Cortisone, C21H28O5(f)
The isobutyl cation spontaneously rearranges to the tert-butyl cation by a hydride shift, is the rearrangement exergonic or endergonic? Draw what you think the transition state for the hydride shift
Draw an energy diagram for the addition of HBr to 1-pentene. Let one curve on your diagram show the formation of 1-brornopentane product and another curve on the same diagram show the formation of
Make sketches of the transition-state structures involved in the reaction of HBr with 1-pentenc (Problem 6.53). Tell whether each structure resembles reactant or product.
Limonene, a fragrant hydrocarbon found in lemons and oranges, is biosynthesized from geranyl diphosphate by the following pathway. Add curved arrows to show the mechanism of each step. Which step
Epi-Aristolochene, a hydrocarbon found in both pepper and tobacco, is biosynthesized by the following pathway. Add curved arrows to show the mechanism of each step. Which steps involve alkene
Aromatic compounds such as benzene react with alkyl chlorides in the presence of A1C13 catalyst to yield alkylbenzenes. The reaction occurs through a carbocation intermediate, formed by reaction of
Alkenes can be converted into alcohols by acid-catalyzed addition of water. Assuming that Markovnikov?s rule is valid, predict the major alcohol product from each of the following alkenes.
Reaction of 2, 3-dimcthyl-1-butenc with HBr leads to an alkyl bromide, C6H13Br. On treatment of this alkyl bromide with KOH in methanol, elimination of HBr to give an alkene occurs and a hydrocarbon
One problem with elimination reactions is that mixtures of products are often formed. For example, treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two alkene products.
How many alkene products, including E, Z isomers, might be obtained by dehydration of 3-methyl-3-hexanol with aqueous sulfuricacid?
What product would you expect to obtain from addition of Cl2 to 1, 2-dimcthyl- cyclohexane? Show the stereochemistry of the product.
Addition of HC1 to 1, 2-dimethylcyclohexene yields a mixture of two products. Show the stereochemistry of each, and explain why a mixture is formed.
What product would you expect from the reaction of cyclopentane with NBS and water? Show the stereo chemistry.
When an unsymmetrical alkene such as propene is treated with N-Bromosuccinimide in aqueous dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon
What products would you expect from oxymercuration of the following alkenes?
What alkenes might the following alcohols have been prepared from?
Show the structures of the products you would obtain by hydroboration/oxidation of the following alkenes:
What alkenes might be used to prepare the following alcohols by hydroboration/oxidation?
The following cycloalkene gives a mixture of two alcohols on hydroboration followed by oxidation. Draw the structures of both, and explain the result.
What products would you expect from the following reactions?
What product would you obtain from catalytic hydrogenation of the following alkenes?
What product would you expect from reaction of cis-2-butene with meta-chloro-peroxybenzoic acid? Show the stereo chemistry.
How would you prepare each of the following compounds starting with analkene?
What products would you expect from reaction of 1-methylcyclohexene with the following reagents?(a) Aqueous acidic KMnO4(b) O3, followed by Zn, CH3CO2H
Propose structures for alkenes that yield the following products on reaction with ozone followed by treatment with Zn:(a) (CH3)2C = O + H2C = O(b) 2 equiv CH3CH2CH = O
Problem 7.18 Show the monomer units you would use to prepare the following polymers:
One of the chain-termination steps that sometimes occurs to interrupt polymerization is the following reaction between two radicals. Propose a mechanism for the reaction, using fishhook arrows to
Name the following alkenes, and predict the products of their reaction with (1) meta-chloroperoxybenzoic acid, (ii) KMnO4 in aqueous acid, and (iii) O3, followed by Zn in aceticacid:
Draw the structures of alkenes that would yield the following alcohols on hydration (red = O). Tell in each case whether you would use hydroboration/oxidation oroxymercuration.
The following alkene undergoes hydroboration/oxidation to yield a single product rather than a mixture. Explain the result, and draw the product showing its stereo chemistry.
From what alkene was the following 1, 2-diol made, and what method was used, epoxide hydrolysis or OsO4?
Predict the products of the following reactions (the aromatic ring is un-reactive in all cases). Indicate region-chemistry when relevant.
Suggest structures for alkenes that give the following reaction products. There may be more than one answer for some cases.
Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:
How would you carry out the following transformations? Tell the reagents you would use in each case.
Which reaction would you expect to be faster, addition of HBr to cyclohexene or to 1-methylcyclohexane? Explain.
What Product will result from hydroboration/oxidation of 1-methylcyclo-pentene with deuterated borane, BD3? Show both the stereochemistry (spatial arrangement) and the regiochemistry (orientation) of
Draw the structure of an alkene that yields only acetone, (CH3)2C = O, on ozonolysis followed by treatment with Zn.
Show the structures of alkenes that give the following products on oxidative cleavage with KMnO4 in acidic solution:
Compound A has the formula C10H16. On catalytic hydrogenation over palladium, it reacts with only I molar equivalent of H2. Compound A also undergoes reaction with ozone, followed by zinc treatment,
An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic
Using an oxidative cleavage reaction, explain how you would distinguish between the following two isomericdienes:
Compound A, C10H18O, undergoes reaction with dilute H2SO4 at 50 °C to yield a mixture of two alkenes, C10H16.The major alkene product, B, gives only Cyclopentanone after ozone treatment followed by
The cis and trans isomers of 2-butene give different Cyclopropane products in the Simmons?Smith reaction. Show the structure of each, and explain the difference.
Iodine azide, IN3, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a mono-substituted alkene such as 1-butene is used, only one product results: (a) Add lone-pair
10-Bromo-α-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from γ-bisabolene by the following route: Draw the structures of the intermediate bromonium and cyclic
Draw the structure of a hydrocarbon that absorbs 2 molar equivalents of H2 on catalytic hydrogenation and gives only butane dial onozonolysis.
Simmons—Smith reaction of cyclohexane with di iodomethane gives a single Cyclopropane product, but the analogous reaction of cyclohexane with 1, 1-diiodoethane gives (in low yield) a mixture of two
In planning the synthesis of one compound from another, it?s just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the
Which of the following alcohols could not be made selectively by hydroboration oxidation of an alkene? Explain.
Predict the products of the following reactions. Don?t worry about the size of the molecule; concentrate on the functional groups.
The sex attractant of the common housefly is a hydrocarbon with the formula C23H46. On treatment with aqueous acidic KMnO4, two products are obtained, CH3 (CH2) 12CO2H and CH3 (CH2) 7CO2H. Propose a

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