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Chapter 22: Problem 56

Draw the structural formula for each of the following. a. formaldehyde (methanal) b. 4 -heptanone c. 3 -chlorobutanal d. 5,5 -dimethyl-2-hexanone

Short Answer

Expert verified
a. Formaldehyde (methanal): H-C=O b. 4-heptanone: CH3-CH2-CH2-CH2-CO-CH2-CH3 c. 3-chlorobutanal: H3C-CH(Cl)-CH2-CH=O d. 5,5-dimethyl-2-hexanone: CH3-CO-CH-CH2-CH(CH3)2

Step by step solution

01

Compound a: Formaldehyde (methanal)

Formaldehyde is the simplest aldehyde with one carbon atom, making it methanal according to IUPAC nomenclature. The aldehyde functional group is -CHO. Hence, the structural formula for formaldehyde is: H ' H - C = O ' H
02

Compound b: 4-heptanone

4-heptanone is a ketone with a seven-carbon atom chain (hept- prefix). The ketone functional group is -CO-, and the number "4" indicates that it is attached to the 4th carbon atom. The structural formula for 4-heptanone is: CH3-CH2-CH2-CH2-CO-CH2-CH3
03

Compound c: 3-chlorobutanal

3-chlorobutanal is an aldehyde with a four-carbon atom chain (but- prefix) and a chlorine atom (chloro) attached to the third carbon atom. The aldehyde group is -CHO, attached to the first carbon atom (terminal). The structural formula for 3-chlorobutanal is: Cl ' H3C-CH-CH2-CH=O ' H
04

Compound d: 5,5-dimethyl-2-hexanone

5,5-dimethyl-2-hexanone is a ketone with a six-carbon atom chain (hex- prefix). The ketone functional group is -CO-, and it is attached to the second carbon atom. There are two methyl groups (-CH3) attached to the fifth carbon atom, as indicated by the (5,5-dimethyl) prefix. The structural formula for 5,5-dimethyl-2-hexanone is: CH3 ' CH3-CO-CH-CH2-CH(CH3)2 ' H

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Most popular questions from this chapter

When toluene \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{3}\right)\) reacts with chlorine gas in the presence of iron(III) catalyst, the product is a mixture of the ortho and para isomers of \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{ClCH}_{3} .\) However, when the reaction is light-catalyzed with no \(\mathrm{Fe}^{3+}\) catalyst present, the product is \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}\). Explain.

Draw the five structural isomers of hexane \(\left(\mathrm{C}_{6} \mathrm{H}_{14}\right)\).

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?

Reagents such as \(\mathrm{HCl}, \mathrm{HBr}\), and \(\mathrm{HOH}\left(\mathrm{H}_{2} \mathrm{O}\right)\) can add across carbon- carbon double and triple bonds, with \(\mathrm{H}\) forming a bond to one of the carbon atoms in the multiple bond and \(\mathrm{Cl}, \mathrm{Br}\), or OH forming a bond to the other carbon atom in the multiple bond. In some cases, two products are possible. For the major organic product, the addition occurs so that the hydrogen atom in the reagent attaches to the carbon atom in the multiple bond that already has the greater number of hydrogen atoms bonded to it. With this rule in mind, draw the structure of the major product in each of the following reactions. a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{H}_{2} \mathrm{O} \stackrel{\mathrm{H}^{*}}{\longrightarrow}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{HBr} \longrightarrow\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}+2 \mathrm{HBr} \longrightarrow\) d. CC1=CCCC1 e. Cl CC=C(C)CC

Minoxidil \(\left(\mathrm{C}_{9} \mathrm{H}_{15} \mathrm{~N}_{5} \mathrm{O}\right)\) is a compound produced by Pharmacia Company that has been approved as a treatment of some types of male pattern baldness. a. Would minoxidil be more soluble in acidic or basic aqueous solution? Explain. b. Give the hybridization of the five nitrogen atoms in minoxidil. c. Give the hybridization of each of the nine carbon atoms in minoxidil. d. Give approximate values of the bond angles marked \(a, b, c\), \(d\), and \(e .\) e. Including all the hydrogen atoms, how many \(\sigma\) bonds exist in minoxidil? f. How many \(\pi\) bonds exist in minoxidil?
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