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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

In the resolution of 1-phenylethylamine using (+)-malic acid, the compound obtained by recrystallization of the mixture of diastereomeric salts is (R)-1-phenylethylammonium (S)-malate. The other
Write structural formulas or make molecular models for all the compounds that are trichloro derivatives of cyclopropane. (Don’t forget to include stereoisomers.) Which are chiral? Which are achiral?
Which of the isomeric alcohols having the molecular formula C5H12O are chiral? Which are achiral?
In each of the following pairs of compounds one is chiral and the other is achiral. Identify each compound as chiral or achiral, as appropriate.
Compare 2, 3-pentanediol and 2, 4-pentanediol with respect to the number of stereoisomers possible for each constitution. Which stereoisomers are chiral? Which are achiral?
In 1996, it was determined that the absolute configuration of (+)-bromochlorofluoromethane is R. Which of the following is (are) (+)-BrClFCH?
Specify the configuration at R or S in each of the following.
A subrule of the Cahn–Ingold–Prelog system specifies that higher mass number takes precedence over lower when distinguishing between isotopes. (a) Determine the absolute configurations of the
Identify the relationship in each of the following pairs. Do the drawings represent constitutional isomers or stereoisomers, or are they just different ways of drawing the same compound? If they are
Chemical degradation of chlorophyll gives a number of substances including phytol. The constitution of phytol is given by the name 3, 7, 11, 15-tetramethyl-2-hexadecen-1-ol. How many stereoisomers
Muscarine is a poisonous substance present in the mushroom Amanita muscaria. Its structure is represented by the constitution shown.
Ectocarpene is a volatile, sperm cell-attracting material released by the eggs of the seaweed Ectocarpus siliculosus. Its constitution is
Multifidene is a sperm cell-attracting substance released by the female of a species of brown algae (Cutleria multifida). The constitution of multifidene is
Streptimidone is an antibiotic and has the structure shown. How many diastereomers of Streptimidone are possible? How many enantiomers? Using the E, Z and R, S descriptors, specify all essential
In Problem 4.26 you were asked to draw the preferred conformation of menthol on the basis of the information that menthol is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. We can
A certain natural product having [a] D+ 40.3° was isolated. Two structures have been independently proposed for this compound. Which one do you think is more likely to be correct? Why?
One of the principal substances obtained from archaea (one of the oldest forms of life on earth) is derived from a 40-carbon diol. Given the fact that this diol is optically active, is it compound A
(a) An aqueous solution containing 10 g of optically pure fructose was diluted to 500 mL with water and placed in a polarimeter tube 20 cm long. The measured rotation was _5.20°. Calculate the
Write the organic products of each of the following reactions. If two stereoisomers are formed, show both. Label all stereogenic centers R or S as appropriate. (a) 1-Butene and hydrogen iodide (b)
The enzyme aconitase catalyzes the hydration of aconitic acid to two products: citric acid and isocitric acid. Isocitric acid is optically active; citric acid is not. What are the respective
Consider the ozonolysis of trans-4, 5-dimethylcyclohexene having the configuration shown.
(a) On being heated with potassium ethoxide in ethanol (70°C), the deuterium-labeled alkyl bromide shown gave a mixture of 1-butene, cis-2-butene, and trans-2-butene. On the basis of your knowledge
A compound (C6H10) contains a five-membered ring. When Br2 adds to it, two diastereomeric dibromides are formed. Suggest reasonable structures for the compound and the two dibromides.
When optically pure 2, 3-dimethyl-2-pentanol was subjected to dehydration, a mixture of two alkenes was obtained. Hydrogenation of this alkene mixture gave 2, 3-dimethylpentane, which was 50%
When (R)-3-buten-2-ol is treated with a peroxy acid, two stereoisomeric epoxides are formed in a 60:40 ratio. The minor stereoisomer has the structure shown.
Use curved arrows to show how calcium carbide reacts with water to give acetylene.
Write structural formulas and give the IUPAC names for all the alkynes of molecular formula C5H8.
How do bond distances and bond strengths change with electronegativity in the series NH3, H2O, and HF?
Complete each of the following equations to show the conjugate acid and the conjugate base formed by proton transfer between the indicated species. Use curved arrows to show the flow of electrons,
Outline efficient syntheses of each of the following alkynes from acetylene and any necessary organic or inorganic reagents: (a) 1-Heptyne (b) 2-Heptyne (c) 3-Heptyne
Which of the alkynes of molecular formula C5H8 can be prepared in good yield by alkylation or, dialkylation of acetylene? Explain why the preparation of the other C5H8 isomers would not be practical.
Give the structures of three isomeric dibromides that could be used as starting materials for the preparation of 3,3-dimethyl-1-butyne.
Show, by writing an appropriate series of equations, how you could prepare propyne from each of the following compounds as starting materials, You may use any necessary organic or inorganic reagents.
Write a series of equations showing how you could prepare octane from acetylene and any necessary organic and inorganic reagents.
Oleic acid and stearic acid are naturally occurring compounds, which can be isolated from various fats and oils. In the laboratory, each can be prepared by hydrogenation of a compound known as
Sodium–ammonia reduction of stearolic acid (see Problem 9.10) yields a compound known as elaidic acid. What is the structure of elaidic acid?
Suggest efficient syntheses of (E) - and (Z)-2-heptene from propyne and any necessary organic or inorganic reagents.
Write a series of equations showing how you could prepare 1, 1-dichloroethane from (a) Ethylene (b) Vinyl chloride (CH2 = CHCl) (c) 1, 1-Dibromoethan
Give the structure of the enol formed by hydration of 2-butyne, and write a series of equations showing its conversion to its corresponding ketone isomer.
Show by a series of equations how you could prepare 2-octanone from acetylene and any necessary organic or inorganic reagents. How could you prepare 4-octanone?
A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis gave CH3 (CH2)4CO2H and HO2CCH2CH2CO2H as the only products. Suggest a reasonable structure for this
Write structural formulas and give the IUPAC names for all the alkynes of molecular formula C6H10.
Provide the IUPAC name for each of the following alkynes: (a) CH3CH2CH2CP ≡ CH (b) CH3CH2CP ≡ CCH3 (c) CH3C ≡ CHCH (CH3)2 CH3
Write a structural formula or build a molecular model of each of the following: (a) 1-Octyne (b) 2-Octyne (c) 3-Octyne (d) 4-Octyne (e) 2, 5-Dimethyl-3-hexyne (f) 4-Ethyl-1-hexyne (g)
All the compounds in Problem 9.19 are isomers except one. Which one?
Write structural formulas for all the alkynes of molecular formula C8H14 that yield 3-ethylhexane on catalytic hydrogenation.
An unknown acetylenic amino acid obtained from the seed of a tropical fruit has the molecular formula C7H11NO2- On catalytic hydrogenation over platinum this amino acid yielded homoleucine (an amino
Show by writing appropriate chemical equations how each of the following compounds could be converted to 1-hexyne: (a) 1, 1-Dichlorohexane (c) Acetylene (b) 1-Hexene (d) 1-Iodohexane
Show by writing appropriate chemical equations how each of the following compounds could be converted to 3-hexyne: (a) 1-Butene (b) 1, 1-Dichlorobutane (c) Acetylene
When 1, 2-dibromodecane was treated with potassium hydroxide in aqueous ethanol, it yielded a mixture of three isomeric compounds of molecular formula C10H19Br. Each of these compounds was converted
Write the structure of the major organic product isolated from the reaction of 1-hexyne with (a) Hydrogen (2 mol), platinum (b) Hydrogen (1 mol), Lindlar palladium (c) Lithium in liquid
Write the structure of the major organic product isolated from the reaction of 3-hexyne with (a) Hydrogen (2 mol), platinum (b) Hydrogen (1 mol), Lindlar palladium (c) Lithium in liquid
When 2-heptyne was treated with aqueous sulfuric acid containing mercury (II) sulfate, two products, each having the molecular formula C7H14O, were obtained in approximately equal amounts. What are
The alkane formed by hydrogenation of (S)-4-methyl-1-hexyne is optically active, but the one formed by hydrogenation of (S)-3-methyl-1-pentyne is not. Explain. Would you expect the products of
All the following reactions have been described in the chemical literature and proceed in good yield. In some cases the reactants are more complicated than those we have so far encountered.
The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe a synthesis of 2-heptanone from acetylene
(Z)-9-Tricosene [(Z)-CH3 (CH2)7CH=CH (CH2)12CH3] is the sex pheromone of the female housefly. Synthetic (Z)-9-tricosene is used as bait to lure male flies to traps that contain insecticide. Using
Show by writing a suitable series of equations how you could prepare each of the following compounds from the designated starting materials and any necessary organic or inorganic reagents: (a) 2,
Assume that you need to prepare 4-methyl-2-pentyne and discover that the only alkynes on hand are acetylene and propyne. You also have available methyl iodide, isopropyl bromide, and 1,
Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B
Write a structural formula for the principal organic product formed in the reaction of methyl bromide with each of the following compounds: (a) NaOH (sodium hydroxide) (b) KOCH2CH3 (potassium
A single organic product was obtained when 1-bromo-3-chloropropane was allowed to react with one molar equivalent of sodium cyanide in aqueous ethanol. What was this product?
Is the two-step sequence depicted in the following equations consistent with the second-order kinetic behavior observed for the hydrolysis of methyl bromide?
The Fischer projection formula for (+)-2-bromooctane is shown. Write the Fischer projection of the (+)-2-octanol formed from it by nucleophilic substitution with inversion of configuration.
Would you expect the 2-octanol formed by SN2 hydrolysis of (+) - 2-bromooctane to be optically active? If so, what will be its absolute configuration and sign of rotation? What about the 2-octanol
Sodium nitrite (NaNO2) reacted with 2-iodooctane to give a mixture of two constitutionally isomeric compounds of molecular formula C8H17NO2 in a combined yield of 88%. Suggest reasonable structures
Suggest a structure for the product of nucleophilic substitution obtained on Solvolysis of tert-butyl bromide in methanol, and outline a reasonable mechanism for its formation.
Identify the compound in each of the following pairs that reacts at the faster rate in an SN1 reaction: (a) Isopropyl bromide or isobutyl bromide (b) Cyclopentyl iodide or 1-methylcyclopentyl
Identify the compound in each of the following pairs that reacts with sodium iodide in acetone at the faster rate: (a) 1-Chlorohexane or cyclohexyl chloride (b) 1-Bromopentane or
What two stereoisomeric substitution products would you expect to isolate from the hydrolysis of cis-1, 4-dimethylcyclohexyl bromide? From hydrolysis of trans-1, 4-dimethylcyclohexyl bromide
Why does the carbocation intermediate in the hydrolysis of 2-bromo-3-methylbutane rearrange by way of a hydride shift rather than a methyl shift?
Predict the major organic product of each of the following reactions: (a) Cyclohexyl bromide and potassium ethoxide (b) Ethyl bromide and potassium cyclohexanolate (c) sec-Butyl bromide solvolysis
Write a chemical equation showing the preparation of octadecyl p-toluenesulfonate.
Write equations showing the reaction of octadecyl p-toluenesulfonate with each of the following reagents: (a) Potassium acetate (KOCCH3) (b) Potassium iodide (KI) (c) Potassium cyanide (KCN) (d)
The hydrolysis of sulfonate esters of 2-octanol is a stereospecific reaction and proceeds with complete inversion of configuration. Write a structural formula that shows the stereochemistry of the
Treatment of 3-methyl-2-butanol with hydrogen chloride yielded only a trace of 2-chloro-3-methylbutane. An isomeric chloride was isolated in 97% yield. Suggest a reasonable structure for this product.
Write the structure of the principal organic product to be expected from the reaction of 1-bromopropane with each of the following: (a) Sodium iodide in acetone (CH3CONa) (b) Sodium acetate in
All the reactions of 1-bromopropane in the preceding problem give the product of nucleophilic substitution in high yield. High yields of substitution products are also obtained in all but one of the
Each of the following nucleophilic substitution reactions has been reported in the chemical literature. Many of them involve reactants that are somewhat more complex than those we have dealt with to
Each of the reactions shown involves nucleophilic substitution. The product of reaction (a) s an isomer of the product of reaction (b) What kind of isomer? By what mechanism does nucleophilic
Arrange the isomers of molecular formula C4H9Cl in order of decreasing rate of reaction with sodium iodide in acetone.
There is an overall 29-fold difference in reactivity of 1-chlorohexane, 2-chlorohexane, and 3-chlorohexane toward potassium iodide in acetone. (a) Which one is the most reactive? Why? (b) Two of
In each of the following indicate which reaction will occur faster. Explain your reasoning. (a) CH3CH2CH2CH2Br or CH3CH2CH2CH2I with sodium cyanide in dimethyl sulfoxide (b) 1-Chloro-2-methylbutane
Under conditions of photochemical chlorination, (CH3)3CCH2C (CH3)3 gave a mixture of two monochlorides in a 4:1 ratio. The structures of these two products were assigned on the basis of their SN1
The compound KSCN is a source of thiocyanate ion. (a) Write the two most stable Lewis structures for thiocyanate ion and identify the atom in each that bears a formal charge of _1. (b) Two
Reaction of ethyl iodide with triethylamine yields a crystalline compound C8H20NI in high yield. This compound is soluble in polar solvents such as water but insoluble in nonpolar ones such as
Write an equation, clearly showing the stereochemistry of the starting material and the product, for the reaction of (S)-1-bromo-2-methylbutane with sodium iodide in acetone. What is the
Identify the product in each of the following reactions:
Give the mechanistic symbols (SN1, SN2, E1, E2) that are most consistent with each of the following statements: (a) Methyl halides react with sodium ethoxide in ethanol only by this mechanism. (b)
Outline an efficient synthesis of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (a) Cyclopentyl cyanide from cyclopentane (b)
Select the combination of alkyl bromide and potassium alkoxide that would be the most effective in the syntheses of the following ethers:
Alkynes of the type RCPCH may be prepared by nucleophilic substitution reactions in which one of the starting materials is sodium acetylide (a) Devise a method for the preparation of CH3CH2C
Give the structures, including stereochemistry, of compounds A and B in the following sequence of reactions:
(a) Suggest a reasonable series of synthetic transformations for converting trans-2-methylcyclopentanol to cis-2-methylcyclopentyl acetate.
Optically pure (S)-(+)-2-butanol was converted to its methanesulfonate ester according to the reaction shown.
In a classic experiment, Edward Hughes (a colleague of in gold’s at University College, London) studied the rate of racemization of 2-iodooctane by sodium iodide in acetone and compared it with the
The ratio of elimination to substitution is exactly the same (26% elimination) for 2-bromo-2-methylbutane and 2-iodo-2-methylbutane in 80% ethanol/20% water at 25°C. (a) By what mechanism does
The reaction of 2, 2-dimethyl-1-propanol with HBr is very slow and gives 2-bromo-2 methyl propane as the major product.
Solvolysis of 2-bromo-2-methylbutane in acetic acid containing potassium acetate gave three products. Identify them.
Solvolysis of 1, 2-dimethylpropyl p-toluenesulfonate in acetic acid (75°C) yields five different products: three are alkenes and two are substitution products. Suggest reasonable structures for

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