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Chapter 5: Problem 184

Alkenes and alkynes on reductive ozonolysis yield carbonyl compounds, whereas on oxidative ozonolysis they give carbonyl or carboxyl compounds, depending on the subtituents. Aldehydes, ketones and carboxylic acids can also be obtained by the oxidation of alcohols. Aldehydes and ketones undergo a variety of nucleophilic addition reactions Which of the following alcohol will not give a carbonyl compound when the vapours of alcohol are passed through red hot copper tube? (a) 3 -methyl-pentan-1-ol (b) 4 -methyl-hexan-2-ol (c) Butan-1-ol (d) 2 - methyl-propan-2-ol

Short Answer

Expert verified
a) 3-methyl-pentan-1-ol b) 4-methyl-hexan-2-ol c) butan-1-ol d) 2-methyl-propan-2-ol Answer: d) 2-methyl-propan-2-ol

Step by step solution

01

First Alcohol: 3-methyl-pentan-1-ol

The structure of 3-methyl-pentan-1-ol is CH3-CH2-CH(CH3)-CH2-CH2-OH. If this alcohol undergoes dehydrogenation, it will form an aldehyde, CH3-CH2-CH(CH3)-CH2-CHO, which is a carbonyl compound.
02

Second Alcohol: 4-methyl-hexan-2-ol

The structure of 4-methyl-hexan-2-ol is CH3-CH(OH)-CH2-CH(CH3)-CH2-CH3. If this alcohol undergoes dehydrogenation, it will form a ketone, CH3-CO-CH2-CH(CH3)-CH2-CH3, which is a carbonyl compound.
03

Third Alcohol: Butan-1-ol

The structure of butan-1-ol is CH3-CH2-CH2-CH2-OH. If this alcohol undergoes dehydrogenation, it will form an aldehyde, CH3-CH2-CH2-CHO, which is a carbonyl compound.
04

Fourth Alcohol: 2-methyl-propan-2-ol

The structure of 2-methyl-propan-2-ol is (CH3)3-COH. If this alcohol undergoes dehydrogenation, it will form a new compound by removing two hydrogen atoms, but it cannot form a carbonyl compound since the carbon connected to the OH group is already bonded to three other carbons, making it impossible to form a double bond with another oxygen atom.
05

Conclusion

Out of the four alcohol options, 2-methyl-propan-2-ol (option d) will not give a carbonyl compound when the vapors of alcohol are passed through a red hot copper tube.

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Most popular questions from this chapter

The reaction \(\left.\left.\right|_{\text {CHO }} ^{\text {CHO }} \stackrel{\mathrm{NaOH}}{\longrightarrow}\right|_{\text {COONa }}{\text { CH }_{2} \mathrm{OH}}\) is an example of (a) intramolecular aldol condensation (b) mixed Cannizzaro reaction (c) intramolecular Cannizzaro reaction (d) crossed Cannizzaro reaction \(\Omega\)

Eventhough a carboxylic acid contains \(-\mathrm{C}\) - group, it does not form oxime with hydroxyl amine because (a) hydroxyl amine is less reactive to carboxylic acids. (b) in this case hydroxyl amine acts as a reducing agent, oxidized to \(\mathrm{HNO}_{2}\). (c) the \(\sum \mathrm{C}=\mathrm{O}\) group enters into resonance with lone pairs of \(-\mathrm{OH}\) group. (d) the -OH group of carboxylic acid reacts with \(\mathrm{NH}_{2} \mathrm{OH}\).

CC1CCCC(=O)C1C=O 470 \(\stackrel{\mathrm{KOH}}{\longrightarrow}(\mathrm{X})\). The product \((\mathrm{X})\) is (a) CC1CCCC(=O)C1C (b) CC1CCCCC1C (c) CC1CCCC(O)C1C (d) CC1CCC=CC1C=O

The IUPAC name of is CCC(C=O)CC(C)C (a) 2 -ethyl-4-methylpentanal (b) 4 -methyl 2 -ethylpentanal (c) 2 -methylhexanal (d) 2 -ethylhexanal

The reaction of ethanoyl chloride with sodium ethanoate gives (a) Ethyl ethanoate (b) ethanoic anhydride (c) Butane-2,3-dione (d) sodium 3 -oxobutanoate
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