(a)
Interpretation:
The IUPAC name for the ester formed when acetic acid and ethanol react has to be assigned.
Concept Introduction:
Esters are prepared by condensation of
Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester. The general reaction scheme can be given as,
For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.
Rules to obtain IUPAC name and common name for an ester:
- Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
- Name of the alkyl part in the ester is just a name of R group. It can be alkyl, cycloalkyl, or aryl group.
- Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
- To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.
(a)
Answer to Problem 16.97EP
IUPAC name of the ester formed is ethyl ethanoate.
Explanation of Solution
Given carboxylic acid and alcohol structure is,
The reaction between two compounds that are shown above, result in the formation of ester. The structure of the ester formed and the complete reaction can be given as shown below,
The structure of ester is,
The alkyl and acyl group is identified as shown below,
Alkyl group contains only two carbon atoms. Hence alkyl group is named as ethyl. The acyl group contains two carbon atoms. The IUPAC name of carboxylic acid that contains three carbon atoms is ethanoic acid. For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”. This gives the name of acyl part as ethanoate. Therefore IUPAC name of the given ester is ethyl ethanoate.
IUPAC name of the formed ester is assigned.
(b)
Interpretation:
The IUPAC name for the ester formed when ethanoic acid and methanol react has to be assigned.
Concept Introduction:
Esters are prepared by condensation of carboxylic acid with an alcohol. A molecule of water is lost on this reaction. The reaction that takes place in producing esters is known as esterification reaction.
Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester. The general reaction scheme can be given as,
For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.
Rules to obtain IUPAC name and common name for an ester:
- Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
- Name of the alkyl part in the ester is just a name of R group. It can be alkyl, cycloalkyl, or aryl group.
- Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
- To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.
(b)
Answer to Problem 16.97EP
IUPAC name of the ester formed is methyl ethanoate.
Explanation of Solution
Given carboxylic acid and alcohol structure is,
The reaction between two compounds that are shown above, result in the formation of ester. The structure of the ester formed and the complete reaction can be given as shown below,
The structure of ester is,
The alkyl and acyl group is identified as shown below,
Alkyl group contains only one carbon atom. Hence alkyl group is named as methyl. The acyl group contains two carbon atoms. The IUPAC name of carboxylic acid that contains three carbon atoms is ethanoic acid. For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”. This gives the name of acyl part as ethanoate. Therefore IUPAC name of the given ester is methyl ethanoate.
IUPAC name of the formed ester is assigned.
(c)
Interpretation:
The IUPAC name for the ester formed when butyric acid and ethyl alcohol react has to be assigned.
Concept Introduction:
Esters are prepared by condensation of carboxylic acid with an alcohol. A molecule of water is lost on this reaction. The reaction that takes place in producing esters is known as esterification reaction.
Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester. The general reaction scheme can be given as,
For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.
Rules to obtain IUPAC name and common name for an ester:
- Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
- Name of the alkyl part in the ester is just a name of R group. It can be alkyl, cycloalkyl, or aryl group.
- Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
- To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.
(c)
Answer to Problem 16.97EP
IUPAC name of the ester formed is ethyl butanoate.
Explanation of Solution
Given carboxylic acid and alcohol structure is,
The reaction between two compounds that are shown above, result in the formation of ester. The structure of the ester formed and the complete reaction can be given as shown below,
The structure of ester is,
The alkyl and acyl group is identified as shown below,
Alkyl group contains only two carbon atoms. Hence alkyl group is named as ethyl. The acyl group contains four carbon atoms. The IUPAC name of carboxylic acid that contains three carbon atoms is butanoic acid. For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”. This gives the name of acyl part as butanoate. Therefore IUPAC name of the given ester is ethyl butanoate.
IUPAC name of the formed ester is assigned.
(d)
Interpretation:
The IUPAC name for the ester formed when 2-butanol and caproic acid react has to be assigned.
Concept Introduction:
Esters are prepared by condensation of carboxylic acid with an alcohol. A molecule of water is lost on this reaction. The reaction that takes place in producing esters is known as esterification reaction.
Esterification reaction is the one in which the carboxylic acid is condensed with an alcohol (or phenol) in presence of strong acid catalyst to produce ester. The general reaction scheme can be given as,
For naming an ester, it can be structurally viewed in a way that contains an acyl group and an alkyl group.
Rules to obtain IUPAC name and common name for an ester:
- Alkyl part appears first in the IUPAC name and it is followed by the acyl part of ester as a separate word.
- Name of the alkyl part in the ester is just a name of R group. It can be alkyl, cycloalkyl, or aryl group.
- Acyl part present in the ester is named by considering the acid name and replacing the suffix “-ic acid” with “-ate”.
- To obtain the common name the alkyl part name is the same while the acyl part name is derived from the common name of the acid by replacing the suffix “-ic acid” with “-ate”.
(d)
Answer to Problem 16.97EP
IUPAC name of the ester formed is 1-methylpropyl hexanoate.
Explanation of Solution
Given carboxylic acid and alcohol structure is,
The reaction between two compounds that are shown above, result in the formation of ester. The structure of the ester formed and the complete reaction can be given as shown below,
The structure of ester is,
The alkyl and acyl group is identified as shown below,
Alkyl group contains a total of four carbon atoms. In that alkyl group (propyl) a methyl group is substituted in the first carbon atom. Hence alkyl group is named as 1-methylpropyl. The acyl group contains six carbon atoms. The IUPAC name of carboxylic acid that contains three carbon atoms is hexanoic acid. For naming acyl group in ester the suffix “-ic acid” is converted into “-ate”. This gives the name of acyl part as hexanoate. Therefore IUPAC name of the given ester is 1-methylpropyl hexanoate.
IUPAC name of the formed ester is assigned.
Want to see more full solutions like this?
Chapter 16 Solutions
Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th
- Determine if the following salt is neutral, acidic or basic. If acidic or basic, write the appropriate equilibrium equation for the acid or base that exists when the salt is dissolved in aqueous solution. If neutral, simply write only NR. Be sure to include the proper phases for all species within the reaction LiNO3arrow_forwardAn unknown weak acid with a concentration of 0.410 M has a pH of 5.600. What is the Ka of the weak acid?arrow_forward(racemic) 19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. & + EtOH H 2-Oxepanone 1-Cyclopentenecarbaldehydearrow_forward
- R₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…arrow_forwardProvide the reasonable steps to achieve the following synthesis.arrow_forwardIdentify which compound is more acidic. Justify your choice.arrow_forward
- Provide the reasonable steps to achieve the following synthesis.arrow_forwardWhen anisole is treated with excess bromine, the reaction gives a product which shows two singlets in 1H NMR. Draw the product.arrow_forward(ii) Draw a reasonable mechanism for the following reaction: CI NaOH heat OH (hint: SNAr Reaction) :arrow_forward
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Introductory Chemistry: An Active Learning Approa...ChemistryISBN:9781305079250Author:Mark S. Cracolice, Ed PetersPublisher:Cengage Learning
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
World of Chemistry, 3rd editionChemistryISBN:9781133109655Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCostePublisher:Brooks / Cole / Cengage Learning
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning