Organic Chemistry
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Phenacetin is a medicine used to treat mild to moderate pain. Complete the following synthetic scheme used to synthesize phenacetin:
Note: Hints are provided as needed.
Propose a synthetic scheme to produce the indicated C−O bond of the given compound. (Note: –CCl3, which is an electron-withdrawing group, is para to the position where the new bond will form.)
Propose a synthesis for the following compound using benzene as the starting material.
Identify the required reagents for the given reaction sequence.
The compound below is involved in the synthesis of proxymetacaine. Show how to synthesize the compound from phenol.
Benzene undergoes Friedel-Crafts alkylation with an unknown alkyl chloride. The 1H NMR spectrum of the product is shown below. Identify the alkyl chloride used.
Provide the correct reaction sequence for the synthesis of the the aromatic derivative m-nitroacetophenone starting from benzene.
Write the correct synthetic sequence for the conversion of ethylbenzene to the given trisubstituted benzene.
Provide the correct synthetic sequence for the conversion of ethylbenzene to the given trisubstituted benzene.
Propose the synthesis of the given compound starting from toluene. Consider that the para product is the major product and is separable from other products:
1-(bromomethyl)-4-propylbenzene
1-(ethoxymethyl)-4-propylbenzene
Provide the correct reaction sequence for the synthesis of the aromatic derivative p-isopropylbenzenesulfonic acid starting from benzene.
Provide the correct reaction sequence for the synthesis of the aromatic derivative m-bromoacetophenone starting from benzene.
2-methyl-4-chlorophenoxyacetic acid (MCPA) is a herbicide widely used for killing broadleaf weeds. Write the correct reaction sequence for the synthesis of MCPA, starting with phenol and other required reagents and solvents.
Starting with benzene, how is 1-bromo-2-(1-bromobutyl)benzene synthesized?
Starting with benzene, provide a scheme for synthesizing the following derivative using three steps:
Bromothymol blue is a pH indicator that changes color from yellow at an acidic pH less than 6.0 to blue at a basic or alkaline pH greater than 7.6.
i) Propose a mechanism for its conversion into blue dianion under basic conditions.
ii) Use resonance structures to show equivalence between the two phenolic oxygens (each with half a negative charge) in the blue bromothymol blue dianion.
Show how you would synthesize the following compound using Friedel–Crafts acylation and Clemmensen reduction:
Show how you would synthesize the following compound using Friedel–Crafts acylation and other reactions.
Describe how 4-methylstyrene can be synthesized using toluene as the starting material.
tert-Butylhydroquinone (TBHQ) is a synthetic antioxidant commonly used as a preservative in edible oils. Devise an approach for its synthesis from hydroquinone.
Determine the final major product formed in the reaction sequence given below:
Show how this compound can be synthesized using benzene or any other required reagents.
The synthesis of the following compound may require the use of a Pd-catalyzed coupling reaction as the final step.
What major product is expected from the coupling reaction shown below?
Show how the following conversion can be achieved with good yield. Use any necessary reagents.
The electrophilic aromatic substitution reaction rate for thiophene is greater than that of benzene. It often reacts under mild reaction conditions. Substitution in thiophene occurs preferably at position 2.
Draw a mechanism for the acetylation of thiophene. You do not have to show steps for generating the CH3C≡O+ ion. You may begin with thiophene and CH3C≡O+ ion.
Suggest a synthesis of the given compound using benzene as the starting material.
The reaction scheme for the synthesis of 1,2,3,4-tetrahydroisoquinoline-5,8-dione is shown below:
What are the missing reagents?
What are the products of the multistep reaction shown below?
Illustrate three different strategies by which the reaction given below can be carried out.
Write down two possible ways by which the reaction given below can be carried out.
How would you accomplish the synthesis of 1-butyl-4-methylbenzene from toluene?
Predict the final product(s) formed from the sequence of the reactions shown below.
Show how the following compound can be prepared using the given starting material and any necessary reagents.
Provide two synthetic approaches to convert benzene to phenol.
Show how the following compound can be synthesized using the given starting material and any necessary reagents.
Propose a synthetic scheme to produce p-ethoxyaniline from benzene.
Outline the steps showing how phenanthrene can be synthesized from the starting material shown below.
Describe how the compound below can be prepared from benzene as the starting material.
Propose a synthesis route for 1-bromo-2-isobutylbenzene starting from benzene.
Show the steps on how o-bromoaniline can be formed from benzene.
Provide the steps on how the compound shown below can be formed from benzene. Ignore stereochemistry.
Illustrate how m-chlorobutylbenzene can be synthesized from benzene.
Demonstrate how m-ethylnitrobenzene can be produced from benzene.
Show how p-chloroethoxybenzene can be produced from benzene.
Demonstrate how to synthesize p-nitro-N-ethylaniline from benzene.
Illustrate how the compound below can be formed from benzene:
p-ditritiobenzene
How can ibuprofen, the active ingredient in pain relievers, be synthesized from styrene?
4-hydroxybenzylamine is a potential neurotransmitter due to its structural similarity to natural catecholamines. How can 4-hydroxybenzylamine be prepared from phenylmethanamine?