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Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.

(a)CH3CO(CH2)4CH3 (b)CH3(CH2)2CO(CH2)2CH3 (c)CH3(CH2)CO(CH2)2CH3

(d)PhCOPh (e)CH3CH2CH2CHO (f)CH3COCH3

(g)CH3CH2CHBrCH2CH(CH3)CHO (h)Ph-CH=CH-CHO

(i)CH3CH=CH-CH=CH-CHO

(j) (k) (l)

Short Answer

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(a) heptan-2-one

(b)heptan-4-one

(c) heptanal

(d) benzophenone

(e)butanal

(f) propan-2-one

(g) 4-bromo-2-methylhexanal3-phenylprop-2-enal

(h) 3-phenylprop-2-enal

(i) 2E,4E-hexa-2,4-dienal

(j) 2-hydroxycyclohexane-1,3-dione

(k)3-oxocyclopentane-1-carbaldehyde

(l)2S,4R-2,4-dimethylcyclopentan

Step by step solution

01

Systematic Naming of Organic Compounds

A systematic way of naming organic compounds based on their chemical composition and structure is given by the IUPAC nomenclature. IUPAC nomenclature consists of three main parts which are root name, suffix, and prefix. Suffix denote the functional group present whereas the number and name of the substituents are denoted by the prefix. In general, IUPAC name for an organic compound can be written in the form as shown below.

substitutenumber-nameofsubstituentrootnamesuffix

02

Naming of ketones and aldehydes from their structures

(a) The structure of the compound can be drawn as:

heptan-2-one

In this organic compound, ketone functional group is attached to the second carbon atom. Therefore, the IUPAC name of the compound is heptan-2-oneand the common name is methyl pentyl ketone.

(b) The structure of the compound can be drawn as:

heptan-4-one

(c) The structure of the compound can be drawn as:

Heptanal

In this organic compound, aldehyde functional group is attached to the first carbon atom. Therefore, the IUPAC name of the compound is heptanal and the common name is N-heptaldehyde.

(d) The structure of the compound can be drawn as:

benzophenone

The IUPAC name of the compound is benzophenone and the common name is diphenyl ketone.

(e) The structure of the compound can be drawn as:

butanal

In this organic compound, aldehyde functional group is attached to the first carbon atom. Therefore, the IUPAC name of the compound is butanal and the common name is butyraldehyde.

(f) The structure of the compound can be drawn as:

propan-2-one

In this organic compound, ketone functional group is attached to the second carbon atom. Therefore, the IUPAC name of the compound is and the common name is acetone or dimethyl ketone.

(g) The structure of the compound can be drawn as:

4-bromo-2-methylhexanal

In this organic compound, aldehyde functional group is attached to the first carbon atom and a bromine atom is attached to the fourth carbon atom. Therefore, the IUPAC name of the compound is 4-bromo-2-methylhexanal.

(h) The structure of the compound can be drawn as:

3-phenylprop-2-enal

In this organic compound, aldehyde functional group is attached to the first carbon atom and a phenyl group is attached to third carbon atom. Therefore, the IUPAC name of the compound is 3-phenylprop-2-enal and the common name is cinnamaldehyde.

(i) The structure of the compound can be drawn as:

(2E,4E)-hexa-2,4-dienal

The IUPAC name of the compound is (2E,4E)-hexa-2,4-dienal.

(j)The structure of the compound is given as:


2-hydroxyxyclohexane-1,3-dione

In this organic compound, one hydroxy group (-OH) is present at the second carbon atom and the ketone functional group is attached to the first and third carbon atom. Therefore, the IUPAC name of the compound is 2-hydroxyxyclohexane-1,3-dione.


(k)The structure of the compound is given as:

3-oxocyclopentane-1-carbaldehyde

The IUPAC name of the compound is 3-oxocyclopentane-1-carbaldehyde.

(l) The structure of the compound is given as:

(2S,4R)-2,4-dimethylcyclopentan-1-one

The IUPAC name of the compound is (2S,4R)-2,4-dimethylcyclopentan-1-one.

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Most popular questions from this chapter

Question. The mass spectrum of unknown compound A shows a molecular ion at m/z 116 and prominent peaks at m/z 87 and m/z 101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane , and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm-1in the IR spectrum and a weak maximum at 274nm(E =16) in the UV spectrum. The mass spectrum of B shows a molecular ion of m/z 72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z 87 and 101.

Propose a mechanism for the acid-catalyzed reaction of benzaldehyde with methanol to give benzaldehyde dimethyl acetal.

Show what alcohols and carbonyl compounds give the following derivatives.

(a)

(b)

(c)

(d)

(e)

(f)

Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.

(a) bromobenzene → propiophenone

(b) CH3CH2CN → heptan-3-one

(c) benzoic acid → phenyl cyclopentyl ketone

(d) 1-bromo-hept-2-ene → oct-3- enal

Sodium triacetoxyborohydride, NaBHOAc3, is a mild reducing agent that reduces aldehydes more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.

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