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Chapter 16: Problem 15

Draw a structural formula for each compound. (a) 1-Chloro-2-propanone (b) 3-Hydroxybutanal (c) 4-Hydroxy-4-methyl-2-pentanone (d) 3-Methyl-3-phenylbutanal (e) 1,3 -Cyclohexanedione (f) 3-Methyl-3-buten-2-one (g) 5 -Oxohexanal (h) 2,2-Dimethylcyclohexanecarbaldehyde (i) 3-Oxobutanoic acid

Short Answer

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Question: Draw the structural formula for each of the following compounds. a) 1-Chloro-2-propanone b) 3-Hydroxybutanal c) 4-Hydroxy-4-methyl-2-pentanone d) 3-Methyl-3-phenylbutanal e) 1,3-Cyclohexanedione f) 3-Methyl-3-buten-2-one g) 5-Oxohexanal h) 2,2-Dimethylcyclohexanecarbaldehyde i) 3-Oxobutanoic acid

Step by step solution

01

(a) 1-Chloro-2-propanone Structural Formula

First, identify the parent chain with the ketone functional group (C=O) since propanone is a 3-carbon chain with a ketone group. Then, find the location of the chlorine atom, which is at the first carbon atom. The structural formula for 1-chloro-2-propanone is: Cl-CH2-CO-CH3.
02

(b) 3-Hydroxybutanal Structural Formula

Start by identifying a 4-carbon chain with an aldehyde functional group (CHO) for butanal. The hydroxyl group (OH) is located at the third carbon atom. The structural formula for 3-hydroxybutanal is: CH3-CH2-CH(OH)-CHO.
03

(c) 4-Hydroxy-4-methyl-2-pentanone Structural Formula

Begin by decorating a 5-carbon chain (pentanone) with a ketone functional group in position 2. Add a hydroxyl group (OH) and a methyl group (CH3) at the fourth carbon atom. The structural formula for 4-hydroxy-4-methyl-2-pentanone is: CH3-CO-CH2-CH(OH)(CH3)-CH3.
04

(d) 3-Methyl-3-phenylbutanal Structural Formula

The parent chain in this case is a 4-carbon chain with an aldehyde functional group (butanal). Attach a methyl group (CH3) and a phenyl group (C6H5) to the third carbon atom. The structural formula for 3-methyl-3-phenylbutanal is: CH3-CH2-CH(C6H5)(CH3)-CHO.
05

(e) 1,3-Cyclohexanedione Structural Formula

The parent chain is a cyclohexane ring with two ketone functional groups (C=O) at the 1 and 3 positions. The structural formula for 1,3-cyclohexanedione is: O=C-CH2-CH2-CO-CH2-CH2- (cyclic, O=C is position 1 and CO is position 3).
06

(f) 3-Methyl-3-buten-2-one Structural Formula

A 5-carbon chain with a ketone functional group in position 2 and a double bond (C=C) between the first and second carbon atoms is required for butenone. A methyl group (CH3) is attached to carbon atom 3. The structural formula for 3-methyl-3-buten-2-one is: CH3-C(=O)-CH(CH3)-CH=CH2.
07

(g) 5-Oxohexanal Structural Formula

The parent chain is hexanal, a 6-carbon chain with an aldehyde functional group. The ketone (C=O) is in the fifth position. The structural formula for 5-oxohexanal is: CH3-CH2-CH2-CH(C=O)-CHO.
08

(h) 2,2-Dimethylcyclohexanecarbaldehyde Structural Formula

A cyclohexane ring is the parent chain. The compound has an aldehyde functional group attached to the ring and two methyl groups (CH3) on the second carbon of the ring. The structural formula for 2,2-dimethylcyclohexanecarbaldehyde is: CHO-CH(CH3)-CH(CH3)-CH2-CH2-CH2- (cyclic, CHO is at position 1).
09

(i) 3-Oxobutanoic acid Structural Formula

The parent chain is butanoic acid, a 4-carbon chain with a carboxylic acid functional group (COOH). There is a ketone functional group (C=O) at the third carbon atom. The structural formula for 3-oxobutanoic acid is: CH3-CH(C=O)-COOH.

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Most popular questions from this chapter

When cis-2-decalone is dissolved in ether containing a trace of \(\mathrm{HCl}\), an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture.

Write structural formulas for all aldehydes with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}\), and give each its IUPAC name. Which of these aldehydes are chiral?

Using your roadmaps as a guide, show how to convert 1-butanol into racemic 4-octanol. You must use 1-butanol as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.

In Section \(11.5\) we saw that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?

Draw a structural formula for the product formed by treating butanal with each reagent. (a) \(\mathrm{LiAlH}_{4}\) followed by \(\mathrm{H}_{2} \mathrm{O}\) (b) \(\mathrm{NaBH}_{4}\) in \(\mathrm{CH}_{3} \mathrm{OH} / \mathrm{H}_{2} \mathrm{O}\) (c) \(\mathrm{H}_{2} / \mathrm{Pt}\) (d) \(\mathrm{Ag}\left(\mathrm{NH}_{3}\right)_{2}{ }^{+}\)in \(\mathrm{NH}_{3} / \mathrm{H}_{2} \mathrm{O}\) (e) \(\mathrm{H}_{2} \mathrm{CrO}_{4}\), heat (f) \(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{HCl}\) (g) \(\mathrm{Zn}(\mathrm{Hg}) / \mathrm{HCl}\) (h) \(\mathrm{N}_{2} \mathrm{H}_{4}, \mathrm{KOH}\) at \(250^{\circ} \mathrm{C}\) (i) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (j) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}\)
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