![Organic Chemistry - Standalone book](https://www.bartleby.com/isbn_cover_images/9780073511214/9780073511214_largeCoverImage.gif)
Interpretation:
The principal product of each of the given reactions is to be identified.
Concept introduction:
The nitro group can be reduced to primary amine by the catalytic hydrogenation or by the action of iron or tin in hydrochloric acid.
The amides are reduced to
The arenes undergo acylation when reacted with acyl chloride in the presence of aluminum chloride.
When primary amines react with an
The amide can be prepared by the nucleophilic substitution of acyl chloride by amine.
The secondary amine can be converted to tertiary amine when reacted with a primary
In an acidic condition, the amide gets hydrolyzed to corresponding
The aryl diazonium salt is a key intermediate in the synthesis of
Electron donating groups activate the arenes and give electrophilic substitution at ortho-para position.
The reaction of aryl diazonium salt with potassium iodide gives the iodobenzene derivatives.
The aryl cyanide is prepared by the reaction of an aryl diazonium salt with
Chlorobenzene or a bromobenzene can be synthesized from aryl diazonium salt by heating it with cuprous chloride or cuprous bromide in
The aryl amine diazonium salt on reaction with hypophosphorous acid or ethanol
The aromatic fluoride substitution occurs by heating aryl diazonium salt with
The diazonium salt, on hydrolysis, gets converted to phenol.
In the reaction of the phenol and a diazonium salt, the phenol molecule at its para position is coupled with diazonium salt.
The
![Check Mark](/static/check-mark.png)
Answer to Problem 39P
Solution:
a)
b)
c)
d)
e)
f)
g)
h)
i)
j)
k)
l)
m)
n)
o)
p)
q)
r)
s)
Explanation of Solution
a) The given reaction is shown below:
The given reactant has a nitro
b) The given reaction is shown below:
The given reactant has a nitro functional group that gets reduced in the presence of tinchloride in hydrochloric acid followed by hydroxide and converted to amine functional group, as shown in following equation.
c) The given reaction is shown below:
The primary amine, on reaction with acyl chloride, undergoes acylation and forms secondary amide by replacing the chlorine atom directly bonded to carbonyl carbon.
The complete reaction is shown below:
d) The given reaction is shown below:
In the above reaction, the reactants are primary alkyl chloride and secondary amine. The nitrogen atom in a secondary amine acts as a nucleophile and attacks the carbon bonded to the chlorine atom. This nucleophilic substitution converts the secondary amine to a tertiary amine. The complete reaction is shown below:
e) The given reaction is shown below:
The given reactant has amide functional group in an acidic condition that gets hydrolyzed and produces derivatives of carboxylic acid and amine.
Their structures are shown in the following equation:
f) The given reaction is shown below:
The reactant given in this reaction is a secondary amide, which is subjected to reduction by using the reagent lithium aluminum hydride and produces secondary amine, i.e.,
The complete reaction is shown below:
g) The given reaction is shown below:
The aniline, on reaction with heptanal, forms an imine which, on catalytic hydrogenation, forms
h) The given reaction is shown below:
Acetanilide is an aromatic compound; the nitrogen atom bonded to benzene activates the ring and gives acylation at para position when reacted with acyl chloride in presence of aluminum chloride. The structure of the product formed is shown in following equation:
i) The given reaction is shown below:
The given reactant has a nitro functional group that gets reduced to iron in hydrochloric acid followed by hydroxide and converted to amine functional group, as shown in following equation.
j) The given reaction is shown below:
The aryl amino group in the above reactant forms aryl diazonium salt, on reaction with sodium nitrite in acidic condition. This diazonium salt, on hydrolysis, forms a phenol derivative.
The complete equation is shown below:
k) The given reaction is shown below:
The aryl amino group in the above reactant forms aryl diazonium salt on reaction with sodium nitrite in acidic condition. The chloride substitution is done by treating this diazonium salt with cuprous chloride. The complete equation is shown below:
l) The given reaction is shown below:
The aryl amino group in the above reactant forms aryl diazonium salt on reaction with sodium nitrite in acidic condition. The bromide substitution is done by treating this diazonium salt with cuprous bromide. The complete equation is shown below:
m) The given reaction is shown below:
The aryl amino group in the above reactant forms aryl diazonium salt on reaction with sodium nitrite in acidic condition. This diazonium salt, on reaction with
The complete equation is shown below:
n) The given reaction is shown below:
The aryl amino group in the above reactant forms aryl diazonium salt on reaction with sodium nitrite in acidic condition. This aryl diazonium salt, on reaction with potassium iodide, introduces iodine to aryl by substitution reaction. The complete equation is shown below:
o) The given reaction is shown below:
The given reactant has two diazonium saltsand on heating with two molar equivalent of
p) The given reaction is shown below:
The aryl amino group in the above reactant forms aryl diazonium salt on reaction with sodium nitrite in acidic condition. The diazonium salt on treatment with hypophosphorous acid
q) The given reaction is shown below:
The aryl amino group in the above reactant forms aryl diazonium salt on reaction with sodium nitrite in acidic condition. The
r) The given reaction is shown below:
The aniline, when reacted with sodium nitrite in acidic condition, produces aryl diazonium salt and gets coupled at para position to the of hydroxide group of
s) The given reaction is shown below:
In the given aryl amine, the nitrogen is substituted with methyl groups; therefore, like primary aryl amines, the
Want to see more full solutions like this?
Chapter 22 Solutions
Organic Chemistry - Standalone book
- * How many milliliters of 97.5(±0.5) wt% H2SO4 with a density of 1.84(±0.01) g/mL will you need to prepare 2.000 L of 0.110 M H2SO4? * If the uncertainty in delivering H2SO4 is ±0.01 mL, calculate the absolute uncertainty in the molarity (0.110 M). Assume there is negligible uncertainty in the formula mass of NaOH and in the final volume (2.000 L) and assume random error.arrow_forwardYou are tasked with creating a calibration curve for the absorbance of cobalt solutions of various concentrations. You must prepare 5 standards with concentrations between 1.00 mg/L and 10.0 mg/L Co2+. You have a stock solution with a concentration of 40 mg/L Co2+ and all the standard lab glassware including transfer pipets and flasks. Explain how you would make your 5 standard solutions of various concentrations, including what glassware you would use to measure and prepare each solution.arrow_forwardPredict the product and write the mechanism. CH3-CH=CH-CH2-CH3 + NBS- hv CCl4arrow_forward
- How exactly is carbon disulfide used in industry? Specifically, where does it come in during rubber or textile production and what is the chemical processes?arrow_forwardA researcher has developed a new analytical method to determine the percent by mass iron in solids. To test the new method, the researcher purchases a standard reference material sample that is 2.85% iron by mass. Analysis of the iron standard with the new method returns values of 2.75%, 2.89%, 2.77%, 2.81%, and 2.87%. Does the new method produce a result that is significantly different from the standard value at the 95% confidence level?arrow_forwardCreate a drawing of an aceral with at least 2 isopropoxy groups, and a total of 11 carbon atomsarrow_forward
- 4. Predict the major product(s) for each of the following reactions. HBr (1 equiv.) peroxide, A a. b. NBS, peroxide, Aarrow_forwardIn addition to the separation techniques used in this lab (magnetism, evaporation, and filtering), there are other commonly used separation techniques. Some of these techniques are:Distillation – this process is used to separate components that have significantly different boiling points. The solution is heated and the lower boiling point substance is vaporized first. The vapor can be collected and condensed and the component recovered as a pure liquid. If the temperature of the mixture is then raised, the next higher boiling component will come off and be collected. Eventually only non-volatile components will be left in the original solution.Centrifugation – a centrifuge will separate mixtures based on their mass. The mixture is placed in a centrifuge tube which is then spun at a high speed. Heavier components will settle at the bottom of the tube while lighter components will be at the top. This is the technique used to separate red blood cells from blood plasma.Sieving – this is…arrow_forwardBriefly describe a eutectic system.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9780618974122/9780618974122_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305960060/9781305960060_smallCoverImage.gif)