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Chapter 17: Problem 5

Complete the equation for each reaction. (a) COc1ccccc1C(=O)O (b) CCOS(=O)(=O)c1ccccc1

Short Answer

Expert verified
Question: Given the following chemical reactions in SMILES notation, complete the equation for each reaction. (a) COc1ccccc1C(=O)O (b) CCOS(=O)(=O)c1ccccc1 Answer: (a) Cinnamic acid - Decarboxylation: C8H8O3 (cinnamic acid) ->[Heat] C7H6O (benzaldehyde) + CO2 (carbon dioxide) (a) Cinnamic Acid - Ester formation: C8H8O3 (cinnamic acid) + ROH (alcohol) ->[Acid] ORC8H7O2 (ester) + H2O (water) (b) Tosylate ester - Nucleophilic substitution: C8H10O4S (tosylate ester) + Nu- (nucleophile) -> C8H10O3S (product) + Nu-CH2CH3 (nucleophilic substitution product) (b) Tosylate ester - Elimination reaction: C8H10O4S (tosylate ester) ->[Heat] C8H8OS (product) + CH2=CH2 (ethylene)

Step by step solution

01

Understand the given SMILES notation

(a) COc1ccccc1C(=O)O (b) CCOS(=O)(=O)c1ccccc1
02

Convert SMILES to molecular formulas

(a) The given molecule can be written as: C8H8O3, which is the molecular formula for cinnamic acid. (b) The given molecule can be written as: C8H10O4S, which is the molecular formula for benzenesulfonyl ester, also known as tosylate ester.
03

Determine the possible reactions

(a) For cinnamic acid: There are a few possible reactions that cinnamic acid can undergo. Let's focus on the most common reactions, such as decarboxylation or formation of ester from the carboxylic group. (b) For tosylate ester: Tosylate esters are good leaving groups and can be replaced by nucleophiles or involved in elimination reactions.
04

Complete the equations for each reaction

(a) Cinnamic acid - Decarboxylation: C8H8O3 (cinnamic acid) ->[\hspace{0.5cm}Heat\hspace{0.5cm}] C7H6O (benzaldehyde) + CO2 (carbon dioxide) (a) Cinnamic Acid - Ester formation: C8H8O3 (cinnamic acid) + ROH (alcohol) ->[\hspace{0.5cm}Acid\hspace{0.5cm}] ORC8H7O2 (ester) + H2O (water) (b) Tosylate ester - Nucleophilic substitution: C8H10O4S (tosylate ester) + Nu- (nucleophile) -> C8H10O3S (product) + Nu-CH2CH3 (nucleophilic substitution product) (b) Tosylate ester - Elimination reaction: C8H10O4S (tosylate ester) ->[\hspace{0.5cm}Heat\hspace{0.5cm}] C8H8OS (product) + CH2=CH2 (ethylene)

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Most popular questions from this chapter

Name the carboxylic acid and alcohol from which each ester is derived. (a) COC(=O)C1CCCCC1 (b) CC(=O)OC1CCC(OC(C)=O)CC1 (c) CCC=CC(=O)OC(C)C (d) CCOC(=O)CCC(=O)OCC

Show how to convert trans-3-phenyl-2-propenoic acid (cinnamic acid) to each compound. (a) OCC=Cc1ccccc1 (b) O=C(O)CCc1ccccc1 (c) OCCCc1ccccc1

Low-molecular-weight dicarboxylic acids normally exhibit two different \(\mathrm{p} K_{\mathrm{a}}\) values. Ionization of the first carboxyl group is easier than the second. This effect diminishes with molecular size, and for adipic acid and longer chain dicarboxylic acids, the two acid ionization constants differ by about one \(\mathrm{p} K\) unit. $$ \begin{array}{|llll|} \hline \text { Dicarboxylic Acid } & \text { Structural Formula } & \mathrm{p} \kappa_{\mathrm{a} 1} & \mathrm{p} K_{\mathrm{a} 2} \\ \hline \text { Oxalic } & \mathrm{HOOCCOOH} & 1.23 & 4.19 \\ \text { Malonic } & \mathrm{HOOCCH}{ }_{2} \mathrm{COOH} & 2.83 & 5.69 \\ \text { Succinic } & \mathrm{HOOC}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{COOH} & 4.16 & 5.61 \\ \text { Glutaric } & \mathrm{HOOC}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{COOH} & 4.31 & 5.41 \\ \text { Adipic } & \mathrm{HOOC}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{COOH} & 4.43 & 5.41 \\ \hline \end{array} $$ Why do the two \(\mathrm{p} K_{\mathrm{a}}\) values differ more for the shorter chain dicarboxylic acids than for the longer chain dicarboxylic acids?

In Section 17.7B, we suggested that the mechanism of Fischer esterification of carboxylic acids is a model for the reactions of functional derivatives of carboxylic acids. One of these reactions is that of an acid chloride with water (Section 18.4A). Suggest a mechanism for this reaction.

Select the stronger acid in each set. (a) Phenol \(\left(\mathrm{p} K_{\mathrm{a}} 9.95\right)\) and benzoic acid \(\left(\mathrm{p} K_{\mathrm{a}} 4.19\right)\) (b) Lactic acid \(\left(K_{\mathrm{a}} 8.4 \times 10^{-4}\right)\) and ascorbic acid \(\left(K_{\mathrm{a}} 7.9 \times 10^{-5}\right)\)
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