Draw a structural formulas for each compound. (a) Dimethyl carbonate (b) Benzonitrile (c) Isopropyl s-methylhexanoate (d) Diethyl oxalate (e) Ethyl (Z)-2-pentenoate (f) Butanoic anhydride (g) Dodecanamide (h) Ethyl S-hydroxybutanoate (i) Octanoyl chloride (j) Diethyl cis 1 , 2-cyclohexanedicarboxylate (k) Methanesulfonyl chloride (1) \(p\)-Toluenesulfonyl chloride

Short Answer

Expert verified
Based on the given compounds' names, identify and draw the structural formulas. a) Dimethyl carbonate: O=C(OC)OC b) Benzonitrile: C1=CC=CC=C1C#N c) Isopropyl s-methylhexanoate: CC(C)OC(=O)CCC(C)CCC d) Diethyl oxalate: CCOC(=O)C(=O)OCC e) Ethyl (Z)-2-pentenoate: CCOC(=O)CCC/C=C\ f) Butanoic anhydride: CCCC(=O)OC(=O)CCC g) Dodecanamide: CCCCCCCCCCCC(=O)N h) Ethyl S-hydroxybutanoate: CCOC(=O)C(O)CC i) Octanoyl chloride: CCCCCCCC(=O)Cl j) Diethyl cis 1,2-cyclohexanedicarboxylate: CCOC(=O)C1C=CC(=O)OCC=CC1 k) Methanesulfonyl chloride: CS(=O)(=O)Cl l) p-Toluenesulfonyl chloride: CC1=CC=CC=C1S(=O)(=O)Cl

Step by step solution

01

Identify the functional group and carbon chain

In dimethyl carbonate, "di-" prefix indicates two methyl groups, and "carbonate" indicates a functional group with one carbon atom double-bonded to an oxygen atom and single-bonded to two other oxygen atoms.
02

Draw the structure

Based on the given information, we can draw the structure as following: O=C(OC)OC #b) Benzonitrile#
03

Identify the functional group and carbon chain

"Benzonitrile" is a compound composed of a benzene ring and a nitrile functional group (C≡N).
04

Draw the structure

The structure of benzonitrile can be drawn as: C1=CC=CC=C1C#N #c) Isopropyl s-methylhexanoate#
05

Identify the functional group and carbon chain

"Isopropyl" means a carbon chain with two carbons and a branching functional group, "s-methylhexanoate" indicates the ester functional group with a "methyl" group on the second carbon, and a total of six carbons attached to the ester.
06

Draw the structure

The structure of isopropyl s-methylhexanoate can be drawn as: CC(C)OC(=O)CCC(C)CCC #d) Diethyl oxalate#
07

Identify the functional group and carbon chain

"Diethyl" indicates two ethyl groups, and "oxalate" indicates a functional group with two carboxylate groups (O=C-O-).
08

Draw the structure

The structure of diethyl oxalate can be drawn as: CCOC(=O)C(=O)OCC #e) Ethyl (Z)-2-pentenoate#
09

Identify the functional group and carbon chain

"Ethyl" indicates an ethyl group, "pentenoate" refers to a 5-carbon alkene chain with an ester functional group, and (Z) indicates the alkene's cis configuration.
10

Draw the structure

The structure of ethyl (Z)-2-pentenoate can be drawn as: CCOC(=O)CCC/C=C\ #f) Butanoic anhydride#
11

Identify the functional group and carbon chain

"Butanoic" has a 4-carbon chain, and "anhydride" has two carbonyl groups joined by an oxygen atom.
12

Draw the structure

The structure of butanoic anhydride can be drawn as following: CCCC(=O)OC(=O)CCC #g) Dodecanamide#
13

Identify the functional group and carbon chain

"Dodecan" refers to a 12-carbon chain, and "amide" to an amide functional group (NH2 attached to C=O).
14

Draw the structure

The structure of dodecanamide can be drawn as: CCCCCCCCCCCC(=O)N #h) Ethyl S-hydroxybutanoate#
15

Identify the functional group and carbon chain

"Ethyl" indicates an ethyl group, "hydroxy" means an OH functional group, "butanoate" indicates a 4-carbon alkyl chain with an ester functional group, and "S-" indicates that the hydroxy group is on the second carbon.
16

Draw the structure

The structure of ethyl S-hydroxybutanoate can be drawn as: CCOC(=O)C(O)CC #i) Octanoyl chloride#
17

Identify the functional group and carbon chain

"Octanoyl" has an 8-carbon chain, and "chloride" indicates an acyl chloride functional group (C=O attached to Cl).
18

Draw the structure

The structure of octanoyl chloride can be drawn as: CCCCCCCC(=O)Cl #j) Diethyl cis 1,2-cyclohexanedicarboxylate#
19

Identify the functional group and carbon chain

"Diethyl" indicates two ethyl groups, "cis" means cis configuration, "cyclohexane" indicates a 6-carbon ring, and "dicarboxylate" means two carboxylate functional groups.
20

Draw the structure

The structure of diethyl cis 1,2-cyclohexanedicarboxylate can be drawn as: CCOC(=O)C1C=CC(=O)OCC=CC1 #k) Methanesulfonyl chloride #
21

Identify the functional group and carbon chain

"Methane" has a one-carbon chain, "sulfonyl" indicates a sulfonyl functional group (SO2), and "chloride" means a single Cl.
22

Draw the structure

The structure of methanesulfonyl chloride can be drawn as: CS(=O)(=O)Cl #l) \(p\)-Toluenesulfonyl chloride#
23

Identify the functional group and carbon chain

"\(p\)-Toluene" indicates a methyl group in the para position of a benzene ring, and "sulfonyl chloride" has a sulfonyl functional group followed by a Cl.
24

Draw the structure

The structure of \(p\)-toluenesulfonyl chloride can be drawn as: CC1=CC=CC=C1S(=O)(=O)Cl

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Functional Groups in Organic Chemistry
When examining organic compounds, one of the key concepts to understand is the role of functional groups. These are specific groupings of atoms within molecules that are responsible for the characteristic chemical reactions of those compounds. The presence of functional groups gives the compound its unique properties and reactivity patterns.

For instance, in the exercise solution, we see a variety of functional groups, such as the carbonate in dimethyl carbonate, nitrile in benzonitrile, and ester groups in compounds like isopropyl s-methylhexanoate. Each of these groups defines how the molecule will interact with other substances and under different conditions.

To enhance understanding, it is crucial to memorize the common functional groups, such as hydroxyl (-OH), carbonyl (C=O), carboxyl (-COOH), and amine (-NH2), among others. This knowledge facilitates the identification and prediction of organic molecule behavior during chemical reactions.
Identifying the Carbon Chain
The carbon chain identification is crucial for understanding organic molecules' structure. Carbon atoms form the backbone of organic compounds, and recognizing the length and type of carbon chain is essential for constructing their structural formulas.

For example, in a name like 'isopropyl s-methylhexanoate', 'isopropyl' indicates a branched chain with a three-carbon structure, and 'hexanoate' suggests a six-carbon chain in the primary structure. Knowing these prefixes and suffixes simplifies the process of drawing the molecule's structural formula.

Beginners should initially focus on linear chains, and then move on to more complex branched and cyclic structures. Through practice, recognizing chains becomes more intuitive, allowing for rapid interpretation of molecular formulas.
Nomenclature of Organic Compounds
The nomenclature of organic compounds follows a systematic method that conveys information about the molecular structure of the compound. It involves the use of prefixes, infixes, and suffixes to describe the carbon chain length, type of carbon bonds, functional groups, and their positions within the molecule.

For instance, the name 'dodecanamide' immediately tells us that we are dealing with a 12-carbon chain (dodec-) with an amide functional group (-amide). Similarly, the term 'p-toluenesulfonyl chloride' reveals a para-substituted benzene ring with a methyl group and sulfonyl chloride functional group.

Understanding these naming conventions is essential, as it allows students to derive the molecular structure from the name and vice versa. This becomes particularly helpful when encountering complex molecules in advanced organic chemistry.

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Most popular questions from this chapter

The mechanism for hydrolysis of an ester in aqueous acid involves formation of a tetrahedral carbonyl addition intermediate. Evidence in support of this mechanism comes from an experiment designed by Myron Bender. He first prepared ethyl benzoate enriched with oxygen- 18 in the carbonyl oxygen and then carried out acidcatalyzed hydrolysis of the ester in water containing no enrichment in oxygen- 18 . If he stopped the experiment after only partial hydrolysis and isolated the remaining ester, the recovered ethyl benzoate had lost a portion of its enrichment in oxygen- 18 . In other words, some exchange had occurred between oxygen- 18 of the ester and oxygen- 16 of water. Show how this observation bears on the formation of a tetrahedral carbonyl addition intermediate during acid-catalyzed ester hydrolysis.\mathrm{O}$

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