Organic Chemistry
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Determine the major product of the reaction below.
Draw the major product of the reaction shown below.
Edman's degradation of a peptide forms thiazoline which can undergo rearrangement in dilute acid to phenylthiohydantoin (PTH) amino acid. Propose a mechanism for the rearrangement of the thiazoline shown below. (Hint: Thioesters react readily with nucleophiles.)
Draw the expected product for the given reaction.
Give the final product of the reaction shown below.
Suggest a four-step synthesis involving an organocuprate reagent to produce the desired product.
Determine the structure of the compounds corresponding to i-iv for each of the following reactions:
Complete the given reactions.
Identify the reagent(s) that can be used in the following reaction.
Draw the substitution product(s) of the given reaction.
The reaction of an acyl chloride with an aqueous solution of primary or secondary amine forms an amide as the major product. Predict the product formed when acetyl chloride reacts with trimethylamine.
Acetic acid is dissolved in isotopically labeled water (H 2O18) with an acid catalyst. Draw the labeled product(s) formed.
Provide the major substitution product(s) of the reaction below.
Which among the following compounds is expected to be the strongest acid?
Which of the following is the weakest ortho-substituted benzoic acids?
What neutral nucleophile would you use to convert methyl propionate into N-ethylpropionamide?
Determine the identity of the major products obtained in the reaction between benzoyl chloride and each of the compounds shown below.(i) methanol(ii) potassium acetate(iii) 2-methylaniline
Suggest a mechanism for this nucleophilic acyl substitution.
Show how to make each of the compounds shown below using the appropriate acyl chlorides and amines as your starting materials.
Determine the identity of products obtained in each of the reactions shown below.
Suggest a plausible mechanism for the reaction shown below.
Under mild conditions, which of the proposed reactions below would take place quickly?
Show how to synthesize each of the compounds below using appropriate acyl chlorides and alcohols as the starting materials.(i) methyl propionate(ii) phenyl 2-methylhexanoate
Propose a plausible mechanism for the base catalyzed hydrolysis of the compound shown below.
Propose a plausible mechanism for the acid-catalyzed hydrolysis of the compound shown below.
For the following compounds, identify the products that would be obtained upon complete hydrolysis:
Show how to synthesize each of the compounds shown below using alanine as your starting material. Give the structure of each product in your answer.(i) alanine ethyl ester(ii) (cyclohexanecarbonyl) alanine
Give the structures of the products and suggest a plausible mechanism for the reaction shown below.
Using an acid chloride as an intermediate, provide a reaction scheme to synthesize N-cyclopentylcyclopentanecarboxamide from cyclopentanecarboxylic acid and cyclopentanamine.
Provide a reaction scheme for the conversion of the given starting material to the nitrile shown below:
2-cyclohexylacetic acid → 2-cyclohexylacetonitrile
Propose a plausible synthesis that would efficiently carry out the following conversion. Use any necessary additional reagents.
Provide a reaction scheme for synthesizing the compound below, using the suitable carboxylic acid and amine.
Propose a reaction scheme for the synthesis of the specified compound below, utilizing the suitable carboxylic acid and amine.
Provide a plausible synthetic scheme for the following compound, which can be synthesized from a suitable carboxylic acid and amine.
Demonstrate how to synthesize the esters below from suitable alcohols and acyl chlorides:
i)
ii)
Illustrate the use of suitable amines and acyl chlorides to synthesize the amides below:
Demonstrate the use of propionic anhydride and a suitable amine or alcohol to yield the following:
Provide a reaction scheme to synthesize the following compounds. Note: The reaction scheme may involve more than one step.
(i) cyclopentanamine → N-cyclopentylacetamide
(ii) bromocyclopentane → dicyclopentylmethanol
What is the product of the reaction below?
Draw the structures of the expected products for the reaction below.
Draw the structure of the product formed from the reaction below.
Give the structure of the product formed from the reaction below.
Provide a reaction scheme to accomplish the synthesis shown below in good yield.
Phosgene is the acid chloride of carbonic acid. It can react twice just like other acid chlorides.
What is the product of the reaction of phosgene with excess butan-1-ol?
(i) The addition of one mole of 3-methylbutanoyl chloride to a liter of triethylamine resulted in a vigorous exothermic reaction. What is the mechanism for this reaction?
(ii) Once the previous mixture has cooled, one mole of propan-1-ol is added. This resulted in another vigorous exothermic reaction that produced triethylamine, triethylammonium chloride, and propyl 3-methylbutanoate. What is the mechanism for this reaction?
Suggest a mechanism for the reaction between m-toluidine and methyl acetate to yield N-(m-tolyl)acetamide and methanol. In the proposed mechanism, identify the leaving group and determine whether it is suitable for an SN2 reaction.
Outline a mechanism when benzyl propionate and isopropylamine react. Include the structure of the transition state when the leaving group departs. Also, identify the nucleophile and the leaving group.
Describe how the following compounds can be synthesized using anhydride as a starting material. Why is an anhydride a more suitable starting material than an acid chloride?
(i) glutaric acid monamide
(ii) glutaric acid monoethyl ester
Determine the major products obtained from the reaction of cyclopentanecarbonyl chloride with each of the reagents listed below:
(i) toluene and aluminum chloride, followed by water
(ii) excess cyclopentylmagnesium bromide followed by treatment with a dilute acid
(iii) LiAlH(O-t-Bu)3
Arrange the carboxylic acid derivatives listed below in decreasing order of reactivity toward nucleophilic attack at C=O with a strong nucleophile like methoxide.
Propose the most appropriate reactants to use for the conversion below.
Diethyl carbonate is an easy-to-handle liquid reagent that is widely utilized in synthesis. Show how you would synthesize propoxur insecticide using diethyl carbonate as the starting material.
The reaction shown below converts the carboxylic acid into an N-hydroxysuccinimide (NHS) ester to activate it for coupling with an amine. Is a NHS ester more reactive than a simple alkyl ester? Why?
Propose the most appropriate reagent(s) to use for the following conversion.
Propose the multistep synthesis of the following transformation. Use any necessary reagents and solvents.