Give the IUPAC name and (if possible) a common name for each compound.

(a)(b)

(c)(d)

Short Answer

Expert verified

(a) The IUPAC name of the compound is 5-hydroxyhexan-3-oneand the common name isethylβ-hydroxypropylketone

(b) The IUPAC name of the compound is 3-phenylbutanaland the common name is β-phenylbutyraldehyde.

(c) The IUPAC name of the compound is (1R,2R)-2-methoxycyclohexane-1-carbaldehyde.

(d) The IUPAC name of the compound is6,6-dimethylcyclohexa-2,4-dienone

Step by step solution

01

IUPAC 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 denotes the functional group present whereas the number and name of the substituents are denoted by the prefix. In general, the IUPAC name for an organic compound can be written in the form as shown below.

substituentnumber-(nameofsubstituent)(root name)(suffix)

02

Naming of the Given Organic Compounds

(a)

The structure of the compound can be drawn as:

Structure of Compound

In this organic compound, one hydroxy group (-OH)is present at the fifth carbon atom and the ketone functional group is attached to the third carbon atom.Therefore, the IUPAC name of the compound is 5-hydroxyhexan-3-oneand the common name is ethylβ-hydroxypropylketone.

(b)

The structure of the compound can be drawn as:

Structure of Compound

In this organic compound, one phenyl group (Ph)is present at the third carbon atom and the aldehyde functional group is attached to the first carbon atom. Therefore, the IUPAC name of the compound is 3-phenylbutanaland the common name is β-phenylbutyraldehyde.

(c)

The structure of the compound is given as:

Structure of Compound

The IUPAC name of the compound is(1R,2R)-2-methoxycyclohexane-1-carbaldehyde

(d)

The structure of the compound is given as:

Structure of Compound

In this organic compound, two methyl groups are present at the sixth carbon atom and the ketone functional group is attached to the first carbon atom. Also, two double bonds are present at the second and fourth carbon atoms respectively. Therefore, the IUPAC name of the compound is 6,6-dimethylcyclohexa-2,4-dienone.

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Most popular questions from this chapter

Propose a mechanism for both parts of the Wolff-Kishner reduction of cyclohexanone: the formation of the hydrazone, and then the base catalyzed reduction with evolution of nitrogen gas.

Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or asymmetrical alkynes. Show what products would be from hydration fo each compound.

(a) hex-3-yne

(b) hex-2-yne

(c) hex-1-yne

(d) cyclodecyne

(e) 3-methylcyclodecyne

Predict the products formed when cyclopentanone reacts with the following reagents.

(a) CH3NH2 , H+

(b) excess CH3OH , H+

(c) hydroxylamine and weak acid

(d) ethylene glycol and p-toluenesulfuric acid

(e) phenylhydrazine and weak acid

(f) PhMgBr and then mild H3O+

(g) Tollens reagent

(h) sodium acetlylide, then H3O+

(i) hydrazine, then hot. fused KOH

(j) Ph3P=CH2

(k) sodium cyanide

(l) acidic hydrolysis of the product from (k)

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.

Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.

(a)acetaldehydelacticacid,CH3CH(OH)COOH

(b)

(c)

(d)

(e)

(f)

(g)

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