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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
Two products, A and B, are obtained from the reaction of 1-bromobutane with NH3. Compound A reacts with acetyl chloride to form C, and B reacts with acetyl chloride to form D. The IR spectra of C and
Phosgene (COCL2) was used as a poison gas in World War I. Give the product that would be formed from the reaction of phosgene with each of the following reagents: 1. One equivalent of methanol 2.
When Ethyl Ester treated butanedioic acid with thionyl chloride, she was surprised to find that the product she obtained was an anhydride rather than an acyl chloride. Propose a mechanism to explain
Give the products of the following reactions:a.b. c. d. e. f. g. h. i. j.
When treated with an equivalent of methanol, compound A, with molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown below. Identify compound A.
a. Identify the two products obtained from the following reaction:b. Eddie Amine carried out the preceding reaction, but stopped it before it was half over, whereupon he isolated the major product.
An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product is
a. Ann Hydride did not obtain any ester when she added 2,4,6-trimethylbenzoic acid to an acidic solution of methanol. Why? b. Would Ann have encountered the same problem if she had tried to
Match the compound with the appropriate carbonyl IR absorption band: acyl chloride ........................ ~1800 and 1750 cm-1 acid anhydride ..................... ~1640 cm-1 ester
When a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following 1H NMR spectrum. Identify the compound.
List the following compounds in order of decreasing frequency of the carbon-oxygen double-bond stretch:
a. If the equilibrium constant for the reaction of acetic acid and ethanol to form ethyl acetate is 4.02, what will be the concentration of ethyl acetate at equilibrium if the reaction is carried out
The 1H NMR spectra for two esters with molecular formula C8H8O2 are shown below. If each of the esters is added to an aqueous solution with a pH of 10, which of the esters will be hydrolyzed more
Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.a.b. c. d. e. f.
Is the acid-catalyzed hydrolysis of acetamide a reversible or an irreversible reaction? Explain.
The reaction of a nitrile with an alcohol in the presence of a strong acid forms a secondary amide. This reaction is known as the Ritter reaction. The Ritter reaction does not work with primary
The intermediate shown here is formed during the hydroxide-ion-promoted hydrolysis of the ester group. Propose a mechanism for the reaction.
What product would you expect to obtain from each of the following reactions?a.b. c.
Sulfonamides, the first antibiotics, were introduced clinically in 1934 (Sections 25.8 and 30.4). Show how a sulfonamide can be prepared from benzene.
Using the pKa values in Table 17.1, predict the products of the following reactions:a.b. c. d.
a. How could aspirin be synthesized, starting with benzene?b. Ibuprofen is the active ingredient in pain relievers such as Advil®, Motrin®, and Nuprin®. How could ibuprofen be
The following compound has been found to be an inhibitor of penicillinase. The enzyme can be reactivated by hydroxylamine (NH2OH). Propose a mechanism to account for the inhibition and for the
For each of the following reactions, propose a mechanism that will account for the formation of the product:a.b.
Show how Novocain®, a painkiller used frequently by dentists (Section 30.3), can be prepared from benzene.
Catalytic antibodies catalyze a reaction by binding to the transition state, thereby stabilizing it. As a result, the energy of activation is lowered and the reaction goes faster. The synthesis of
Saccharin, an artificial sweetener, is about 300 times sweeter than sucrose. Describe how saccharin could be prepared, using benzene as the starting material.
Information about the mechanism of reaction of a series of substituted benzenes can be obtained by plotting the logarithm of the observed rate constant obtained at a particular pH against the Hammett
Is the following statement true or false? If the newly added group in the tetrahedral intermediate is a stronger base than the group attached to the acyl group in the reactant, formation of the
What will be the product of a nucleophilic acyl substitution reaction-a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction-if the new group in the
Show how the following compounds could be prepared, using ethyne as one of the starting materials. Explain why ethyne should be alkylated before, rather than after, nucleophilic addition. a.
Can a cyanohydrin be prepared by treating a ketone with sodium cyanide?
Explain why aldehydes and ketones react with a weak acid such as hydrogen cyanide in the presence of -C≡N, but do not react with strong acids such as HCl or H2SO4 in the presence Cl- or HSO4-.
What alcohols are obtained from the reduction of the following compounds with sodium borohydride? a. 2-methylpropanal b. Cyclohexanone c. Benzaldehyde d. Acetophenone
What amides would you treat with LiAlH4 in order to prepare the following amines? a. Benzylmethylamine b. Ethylamine c. Diethylamine d. Triethylamine
Starting with N-benzylbenzamide, how would you make the following compounds? a. Dibenzylamine b. Benzoic acid c. Benzaldehyde d. Benzyl alcohol
The pKa of protonated acetone is about -7.5 and the pKa of protonated hydroxylamine is 6.0.a. In its reaction with hydroxylamine at pH = 4.5 (Figure 18.2), what fraction of acetone will be present in
A ketone can be prepared from the reaction of a nitrile with a Grignard reagent. Describe the intermediate that is formed in this reaction, and explain how it can be converted to a ketone.
a. Write the mechanism for the following reactions: 1. The acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine 2. The acid-catalyzed hydrolysis of an enamine to a
Give two names for each of the following compounds:a.b. c. d. e. f.
Give the products of the following reactions. (A catalytic amount of acid is present in each reaction.) a. Cyclopentanone + ethylamine b. Cyclopentanone + diethylamine c. Acetophenone + hexylamine d.
Imines can exist as stereoisomers. The isomers are named by the E, Z system of nomenclature. (The lone pair has the lowest priority.)Draw the structure of each of the following compounds: a.
Semicarbazide has two NH2 groups. Explain why only one of them forms an imine.
Hydration of an aldehyde can also be catalyzed by hydroxide ion. Propose a mechanism for hydroxide-ion-catalyzed hydration.
Trichloroacetaldehyde has such a large equilibrium constant for its reaction with water that the reaction is essentially irreversible. Therefore, chloral hydrate, the product of the reaction, is one
Which of the following ketones has the largest equilibrium constant for the addition of water?
Show the mechanism for the acid-catalyzed hydrolysis of an acetal.
Explain mechanistically why an acetal or ketal can be isolated but most hydrates can't be isolated.
a. Would you expect hemiacetals to be stable in basic solutions? Explain your answer. b. Acetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-. c. Can the rate of
a. What would have been the product of the preceding reaction with LiAlH4 if the keto group had not been protected? b. What reagent could you use to reduce only the keto group?
Why don't acetals react with nucleophiles?
What products would be formed from the preceding reaction if aniline's amino group were not protected?
a. In a six-step synthesis, what will be the yield of the target compound if each of the reactions employed gives an 80% yield? (An 80% yield is a relatively high laboratory yield.) b. What would be
Show how each of the following compounds can be prepared from the given starting material. In each case, you will need to use a protecting group.a.b.
a. What carbonyl compound and what phosphonium ylide are required for the synthesis of the following alkenes?b. What alkyl halide is required to prepare each of the phosphonium ylides?
Which enantiomer is formed when a methyl Grignard reagent attacks the Re face of each of the following carbonyl compounds? a. Propiophenone b. Benzaldehyde c. 2-pentanone d. 3-hexanone
Using bromocyclohexane as a starting material, how could you synthesize the following compounds?
Give the major product of each of the following reactions:a.b. c. d.
Which would give a higher yield of an unsaturated alcohol when treated with sodium borohydride, a sterically hindered ketone or a nonsterically hindered ketone?
Give the major product of each of the following reactions:a.b. c. d.
Which ketone is more reactive? a. 2-heptanone or 4-heptanone b. p-nitroacetophenone or p-methoxyacetophenone
Draw the structure for each of the following compounds: a. Isobutyraldehyde b. 4-hexenal c. Diisopentyl ketone d. 3-methylcyclohexanone e. 2,4-pentanedione f. 4-bromo-3-heptanone g.
Give the products of each of the following reactions:a.b. c. d. e. f. g. h.
List the following compounds in order of decreasing reactivity toward nucleophilic attack:
a. Show the reagents required to form the primary alcohol.b. Which of the reactions cannot be used for the synthesis of isobutyl alcohol? c. Which of the reactions changes the carbon skeleton of the
Using cyclohexanone as the starting material, describe how each of the following compounds could be synthesized:
Propose a mechanism for the following reaction:
List the following compounds in order of decreasing Keq for hydrate formation:
Fill in the boxes:a.b.
Give the products of each of the following reactions:a.b. c. d. e. f. g. h. i. j.
Thiols can be prepared from the reaction of thiourea with an alkyl halide, followed by hydroxide-ion-promoted hydrolysis.a. Propose a mechanism for the reaction. b. What thiol would be formed if the
a. How many isomers are obtained from the reaction of 2-pentanone with ethylmagnesium bromide followed by treatment with aqueous acid? b. How many isomers are obtained from the reaction of
The only organic compound obtained when compound Z undergoes the following sequence of reactions gives the 1H NMR spectrum shown. Identify compound Z.
Propose a mechanism for each of the following reactions:a.b. c.
How many signals would the product of the following reaction show in these spectraa. Its 1H NMR spectrumb. Its 13C NMR spectrum
Give the products of the following reactions. Show all stereoisomers that are formed.a.b. c. d.
List three different sets of reagents (a carbonyl compound and a Grignard reagent) that could be used to prepare each of the following tertiary alcohols:a.b.
Give the product of the reaction of 3-methyl-2-cyclohexenone with each of the following reagents: a. CH3MgBr followed by H3O+ b. Excess NaCN, HCl c. H2, Pd d. HBr e. (CH3CH2)2CuLi followed by H3O+ f.
Norlutin® and Enovid® are ketones that suppress ovulation. Consequently, they have been used clinically as contraceptives. For which of these compounds would you expect the infrared carbonyl
A compound gives the following IR spectrum. Upon reaction with sodium borohydride followed by acidification, the product with the following 1HNMR spectrum is formed. Identify the compounds.
Unlike a phosphonium ylide, which reacts with an aldehyde or ketone to form an alkene, a sulfonium ylide reacts with an aldehyde or ketone to form an epoxide. Explain why one ylide forms an alkene,
Indicate how the following compounds could be prepared from the given starting materials:a.b. c. d. e.
We saw that 3-methyl-3-hexanol can be synthesized from the reaction of 2-pentanone with ethylmagnesium bromide. What two other combinations of ketone and Grignard reagent could be used to prepare the
Propose a reasonable mechanism for each of the following reactions:a.b.
a. In aqueous solution, D-glucose exists in equilibrium with two six-membered ring compounds. Draw the structures of these compounds.b. Which of the six-membered ring compounds will be present in
The 1HNMR spectrum of the alkyl bromide used to make the ylide to form a compound with molecular formula C11H14 is shown below. What product is obtained from the Wittig reaction?
In the presence of an acid catalyst, acetaldehyde forms a trimer known as paraldehyde. Because it induces sleep when it is administered to animals in large doses, paraldehyde is used as a sedative or
The addition of hydrogen cyanide to benzaldehyde forms a compound called mandelonitrile. (R)-Mandelonitrile is formed from the hydrolysis of amygdalin, a compound found in the pits of peaches and
What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?a.b. c. d.
Identify compounds A and B:
Propose a reasonable mechanism for each of the following reactions:a.b.
A compound reacts with methylmagnesium bromide followed by acidification to form the product with the following 1H NMR spectrum. Identify the compound.
Show how each of the following compounds can be prepared from the given starting material. In each case, you will need to use a protecting group.a.b. c.
What product would be obtained from the reaction of one equivalent of a carboxylic acid with one equivalent of a Grignard reagent?
When a cyclic ketone reacts with diazomethane, the next larger cyclic ketone is formed. This is called a ring expansion reaction. Provide a mechanism for this reaction.
The pKa values of oxaloacetic acid are 2.22 and 3.98.a. Which carboxyl group is more acidic? b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the
The Horner-Emmons modification is a variation of a Wittig reaction in which a phosphonate-stabilized carbanion in used instead of a phosphonium ylide.The phosphonate-stabilized carbanion is prepared
In order to solve this problem, you must read the description of the Hammett Ï, Ï treatment given in Chapter 17, Problem 76. When the rate constants for the hydrolysis of
Propose a mechanism for each of the following reactions:a.b. c. d.
a. Which of the following tertiary alcohols cannot be prepared from the reaction of an ester with excess Grignard reagent?b. For those alcohols that can be prepared by the reaction of an ester with
Which of the following secondary alcohols can be prepared from the reaction of methyl formate with excess Grignard reagent?
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