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Chapter 22: Problem 9

Give an example reaction that would yield the following products as major organic products. See Exercises \(22.62\) and \(22.65\) for some hints. For oxidation reactions, just write oxidation over the arrow and don't worry about the actual reagent. a. primary alcohol b. secondary alcohol c. tertiary alcohol d. aldehyde e. ketone f. carboxylic acid g. ester

Short Answer

Expert verified
a. \( CH_{3} - C\equiv CH + BH_{3} \xrightarrow{H_{2}O_{2} / NaOH} CH_{3} - CH_{2} - CH_{2} -OH \) b. \( CH_{3} - CH_{2} -Br + Mg \rightarrow CH_{3}-CH_{2}- MgBr \) \( CH_{3}-CH_{2}-MgBr + CH_{3}C=O \rightarrow CH_{3}-CH(OH)-CH_{3} + MgBrO \) c. \( CH_{3} - C(CH_{3})_{2} + H_{3}C - OH \xrightarrow{AlCl_{3}} (CH_{3})_{3}C - OH \) d. \( CH_{3} - COOEt + DIBAL-H \xrightarrow{-78^{\circ}C} CH_{3} - CHO + H_{3}C - OH + EtAl \) e. \( CH_{3} - C \equiv N + EtMgBr + H_{2}O \rightarrow CH_{3} - COEt + MgBrOH \) f. \( CH_{3} - CHO \xrightarrow{oxidation} CH_{3} - COOH \) g. \( CH_{3} - COOH + CH_{3} - OH \xrightarrow{H_{2}SO_{4}} CH_{3} - COOCH_{3} + H_{2}O \)

Step by step solution

01

a. Primary Alcohol

One method to synthesize a primary alcohol is through the hydroboration-oxidation of terminal alkynes. The reaction generally involves the following steps: 1. Terminal alkyne + BH₃: This forms an organoborane intermediate through regioselective addition of borane to the alkyne. 2. Organoborane + H₂O₂/NaOH: The oxidation reaction transforms organoborane to alcohol. Example Reaction: \( CH_{3} - C\equiv CH + BH_{3} \xrightarrow{H_{2}O_{2} / NaOH} CH_{3} - CH_{2} - CH_{2} -OH \)
02

b. Secondary Alcohol

Secondary alcohols can be synthesized by a Grignard reaction. The stepwise process is as follows: 1. React an alkyl halide with Mg to form Grignard reagent. 2. Mix the Grignard reagent with a ketone, which results in an addition reaction that forms a secondary alcohol. Example Reaction: \( CH_{3} - CH_{2} -Br + Mg \rightarrow CH_{3}-CH_{2}- MgBr \) \( CH_{3}-CH_{2}-MgBr + CH_{3}C=O \rightarrow CH_{3}-CH(OH)-CH_{3} + MgBrO \)
03

c. Tertiary Alcohol

Tertiary alcohols can be synthesized using Friedel-Crafts alkylation. A Lewis acid catalyst is used to form a carbocation. The carbocation reacts with an aromatic ring to form the desired tertiary alcohol. Example Reaction: \( CH_{3} - C(CH_{3})_{2} + H_{3}C - OH \xrightarrow{AlCl_{3}} (CH_{3})_{3}C - OH \)
04

d. Aldehyde

An aldehyde can be formed through the partial reduction of an ester using diisobutylaluminium hydride (DIBAL-H). Example Reaction: \( CH_{3} - COOEt + DIBAL-H \xrightarrow{-78^{\circ}C} CH_{3} - CHO + H_{3}C - OH + EtAl \)
05

e. Ketone

A ketone can be synthesized by reacting a nitrile with a Grignard reagent and water. Example Reaction: \( CH_{3} - C \equiv N + EtMgBr + H_{2}O \rightarrow CH_{3} - COEt + MgBrOH \)
06

f. Carboxylic Acid

Carboxylic acids can be formed through the oxidation of an aldehyde. In this case, we can write "oxidation" over the arrow without specifying the reagent, as mentioned in the exercise. Example Reaction: \( CH_{3} - CHO \xrightarrow{oxidation} CH_{3} - COOH \)
07

g. Ester

Esters can be synthesized through the Fischer esterification reaction, which involves the reaction of a carboxylic acid with an alcohol in the presence of an acid catalyst. Example Reaction: \( CH_{3} - COOH + CH_{3} - OH \xrightarrow{H_{2}SO_{4}} CH_{3} - COOCH_{3} + H_{2}O \)

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Most popular questions from this chapter

Draw structural formulas for each of the following alcohols. Indicate whether the alcohol is primary, secondary, or tertiary. a. 1 -butanol c. 2 -methyl-l-butanol b. 2 -butanol d. 2 -methyl-2-butanol

Name all the alcohols that have the formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\). How many ethers have the formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) ?

Draw a structural formula for each of the following. a. 3-methylpentanoic acid b. ethyl methanoate c. methyl benzoate d. 3 -chloro- 2,4 -dimethylhexanoic acid

Polychlorinated dibenzo- \(p\) -dioxins (PCDDs) are highly toxic substances that are present in trace amounts as by-products of some chemical manufacturing processes. They have been implicated in a number of environmental incidents- for example, the chemical contamination at Love Canal and the herbicide spraying The most toxic \(\mathrm{PCDD}\) is \(2,3,7,8\) -tetrachloro-dibenzo- \(p\) -dioxin. Draw the structure of this compound. Also draw the structures of two other isomers containing four chlorine atoms.

Consider the following reactions. For parts \(\mathrm{b}-\mathrm{d}\), see Exercise \(62 .\) a. When \(\mathrm{C}_{5} \mathrm{H}_{12}\) is reacted with \(\mathrm{Cl}_{2}(g)\) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of \(\mathrm{C}_{5} \mathrm{H}_{12}\) in this reaction? b. When \(\mathrm{C}_{4} \mathrm{H}_{8}\) is reacted with \(\mathrm{H}_{2} \mathrm{O}\), a tertiary alcohol is produced as the major product. What is the structure of \(\mathrm{C}_{4} \mathrm{H}_{8}\) in this reaction? c. When \(\mathrm{C}_{7} \mathrm{H}_{12}\) is reacted with \(\mathrm{HCl}\), 1 -chloro-1-methylcyclohexane is produced as the major product. What are the two possible structures for \(\mathrm{C}_{7} \mathrm{H}_{12}\) in this reaction? d. When a hydrocarbon is reacted with \(\mathrm{H}_{2} \mathrm{O}\) and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? e. When \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) is oxidized, a carboxylic acid is produced. What are the possible structures for \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) in this reaction?
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