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Draw structures to correspond with the following common and systematic names:

(a)phenyl formate

(b)cyclohexyl benzoate

(c)cyclopentyl phenylacetate

(d)N-butylacetamide

(e)N,N-dimethylformamide

(f)benzoic propionic anhydride

(g)benzamide

(h)-hydroxyvaleronitrile

(i)-bromobutyryl chloride

(j)-butyrolactone

(k)phenyl isocyanate

(l)cyclobutyl ethyl carbonate

(m)-caprolactam

(n)trichloroacetic anhydride

(o)ethyl N-methyl carbamate

Short Answer

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Step by step solution

01

Step-by-Step SolutionStep 1: Common names

A nomenclature system is useful for naming simple organic molecules. It often fails for more complex molecules, in which case systematic or IUPAC nomenclature is preferable.

02

Systematic names

A name composed of words or symbols that precisely describe chemical structure, thus allowing the structure of a chemical to be derived from its name.

03

Structures of the given compounds

(a)The molecular formula of phenyl formate is C7H6O2

One phenyl ring and an ester functional group is present in phenyl formate, as the name indicates. So, the structure is:

Structure of phenyl formate



(b)The molecular formula of cyclohexyl benzoate is C13H16O2.

As the name indicates, it is having an ester group attached to benzene ring and to which a cyclohexane ring is also attached.

The structure is as follows:


Structure of cyclohexyl benzoate


(c)The molecular formula of cyclopentyl phenylacetate is C13H16O2

As the name indicates, it is having an acetate group attached to benzene ring and to which a cyclopentane ring is also attached.

The structure is as follows:

Structure of cyclopentyl phenylacetate

(d)The molecular formula of N-butylacetamide is C6H13NO. It has one amide group attached to a butane chain.

Structure of N-butylacetamide

(e)The molecular formula of N,N-dimethylformamide is C3H7NO.

Amide group is present, to which two methyl groups are attached.

Structure of N,N-dimethylformamide

(f)The molecular formula of benzoic propionic anhydride is C10H10O3.

It is having a benzene ring attached to an anhydride group.

Structure of benzoic propionic anhydride

(g) The molecular formula of benzamide isC7H7NOC7H7NO.

It has an linkage between amide group and benzene ring.

Structure of benzamide

(h)The molecular formula of-hydroxyvaleronitrile is C5H9NO.

An alcohol and a cyanide group is present. Alcohol is attached to gamma carbon. The structure is as follows:

Structure of gamma-hydroxyvaleronitrile

(i)The molecular formula ofis C4H6CIBrO

It is having a four carbon chain including aceyl carbon. Bromo group is attached to alpha carbon. The structure of given compound is as follows:

Structure of alpha-bromobutyrylchloride

(j)The molecular formula of beta-butyrolactone isC4H6O2 .

The compound is having a lactone functional group. It is a four carbon chain compound, to which 鈥淥-atom鈥 is attached on beta carbon. It鈥檚 structure is as follows:

Structure of beta-butyrolactone

(k) The molecular formula of phenyl isocynate is C7H5NO.

The compound is having an isocyanate group attached to a benzene ring. It鈥檚 structure is as follows:

Structure of phenyl isocyanate

(l) The molecular formula of cyclobutyl ethyl carbonate is C7H12O3.

It is having following structure.

Structure of cyclobutyl ethyl carbonate

(m) The molecular formula of caprolactamis C6H11NO.

Capro indicates six carbons. It鈥檚 structure is as follows:

Structure of delta-caprolactum

(n)The molecular formula of trichloroacetic anhydride is C4CI6O3.

The compound is having all the terminal hydrogens replaced with Cl. It is having following structure.

Structure of trichloroacetic anhydride

(o)The molecular formula of ethyl N-methyl carbamate C4H9NO2.

Structure of N-methylcarbamate

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Most popular questions from this chapter

(a)Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.

(b) Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.

(c)Propose a secondmechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the otheroxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.

(d)Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.

(e)Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an SN2 reaction?

One mole of acetyl chloride is added to a liter of triethylamine, resulting in a vigorous exothermic reaction. Once the reaction mixture has cooled, 1 mole of ethanol is added. Another vigorous exothermic reaction results. The mixture is analyzed and found to contain triethylamine, ethyl acetate, and triethylammonium chloride. Propose mechanisms for the two exothermic reactions.

When ethyl 4-hydroxybutyrate is heated in the presence of a trace of a basic catalyst (sodium acetate), one of the products is a lactone. Propose a mechanism for the formation of this lactone.

The IR spectra shown next may include a carboxylic acid, an ester, an amide, a nitrile, an acid chloride, or an acid anhydride.

Determine the functional group suggested by each spectrum, and list the specific frequencies you used to make your decision.


Show how you would convert the following starting materials to the indicated nitriles:

(a)phenylaceticacidphenylacetonitrile

(b)phenylaceticacid3-phenylpropionitrile

(c)p-chloronitrobenzenep-chlorobenzonitrile


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