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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

Following is the final step in the synthesis of the antiviral drug Rimantidine (Problem 7.19). (a) Describe experimental conditions to bring about this conversion. (b) Is Rimantidine chiral? How many stereoisomers are possible for it?

Draw a structural formula for the product of each acid-catalyzed reaction. (a) Phenylacetaldehyde \(+\) hydrazine \(\longrightarrow\) (b) Cyclopentanone + semicarbazide \(\longrightarrow\) (c) Acetophenone \(+2,4\)-dinitrophenylhydrazine \(\longrightarrow\) (d) Benzaldehyde \(+\) hydroxylamine \(\longrightarrow\)

In dilute aqueous base, \((R)\)-glyceraldehyde is converted into an equilibrium mixture of \((R, S)\)-glyceraldehyde and dihydroxyacetone. Propose a mechanism for this isomerization.

All rearrangements we have discussed so far have involved generation of an electrondeficient carbon followed by a 1,2 -shift of an atom or group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1 ,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone.

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.
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