Vidallon‚ Mark Louis P. Date Performed: February 20‚ 2012 CHEM44.1 2L Date Submitted: March 12‚ 2012 MIXED-ALDOL CONDENSATION Synthesis of Cinnamaldehyde I. Introduction Cinnamaldehyde‚ cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil‚ extracted from several species of Cinnamomum (C. verum‚ C. burmanii‚ C. cassia)‚ under the family Lauraceae‚ a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil‚ which contains 60-80% cinnamaldehyde
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Aldehydes and Ketones Introduction Aldehydes and ketones share the carbonyl functional group which features carbon doubly bonded to oxygen. In the case of ketones there are two carbon atoms bonded to the carbonyl carbon and no hydrogens. In the case of aldehydes there is at least one hydrogen bonded to the carbonyl carbon; the other attachment may be to a carbon or a hydrogen. In all cases the carbon(s) that are attached to the carbonyl group may be aliphatic (not part of an aromatic ring) or aromatic
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alkenes from carbonyl compounds. The purpose of this experiment is to isolate the trans‚ trans-1‚4-diphenyl-1‚3-butadiene‚ which is formed by a Wittig reaction along with the cis‚ trans isomeric diene. The reaction is carried out in two steps. First the Wittig salt is obtained through a simple nucleophilic displacement of chloride ion by triphenylphosphine. When treated with base‚ the Wittig salt forms a ylide which is a carbanion that acts as a nucleophile and adds to the carbonyl group. In this
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no alpha hydrogen so aldol condensation is not possible. F) Cyclohexanone = contains alpha hydrogen‚ aldol condensation product: 4. Ketones are less reactive than aldehydes in aldol condensations because the carbonyl group on the ketone is more sterically hindered than the carbonyl group on the aldehyde. This sterical hindrance makes a nucleophilic attack less likely. The
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The product formed in an aldol condensation contains and adehydes and an alcohol. Claisen-Schmidt condensation is a crossed aldol condensation that involves an aromatic aldehydes dehydration to yield double bond conjugated aromatic ring and the carbonyl group. Aldol products can dehydrate under either acidic or basic conditions to give‚ α‚ β-unsaturated aldehydes and ketones. Although there is even balance in the equilibrium in aldo condensation‚ the dehydration is usually exothermic. (Wade‚ 1998)
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ketone is the carbonyl group. A carbonyl group is a carbon atom doubly bonded to an oxygen atom. [pic] Both molecules have a carbonyl group‚ the difference the number of carbons bonded to the carbonyl carbon. An aldehyde will have none or one and a ketone will have two carbons. All aldehydes‚ except formaldehyde‚ will have a hydrogen atom on one side of the carbonyl carbon and at least on carbon on the other side. [pic] All ketones have a carbon on each side of the carbonyl carbon. [pic]
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enolate ion to another carbonyl group. The resulting product‚ a beta-hydroxy ketone or aldehyde‚ is called an aldol because it contains both and aldehyde group and the hydroxy group of alcohol. Condensations‚ including aldol condensation‚ combine two or more molecules‚ typically with a loss of a smaller molecule (including water or alcohol). In the presence of a base‚ the aldol condensation occurs by a nucleophilic addition of the enolate ion (a strong nucleophile) to a carbonyl group. The final step
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The dicarboxylic acid has a C=C bond. Problems: 1. The carbonyl that is NOT incorporated into the ring structure has the greater IR stretching frequency. This is because the carbonyl incorporated into the ring structure shares some of its double bond character with the other double bond in the ring‚ giving it more single bond character. Thus‚ conjugated double bonds lower the stretching frequency of a carbonyl group by sharing the dipole character of the
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because of its location near the carbonyl on acetophenone. When the sodium hydroxide is added‚ it deprotonates the hydrogen and creates an enolate ion. This deprotonation creates a nucleophilic carbon that can attack an electrophilic carbon (like a parent carbon of a carbonyl). This enolate ion is a resonance structure and the oxygen atom and the corresponding pi bond it can form can stabilize the negative charge. When the nucleophilic pi bond attacks the carbonyl carbon (the electrophile) it undergoes
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EXPERIMENT 1: REACTIONS OF ENOLATE IONS WITH CARBONYL GROUPS Aims In this experiment we used two techniques for the reactions of enolate ions with carbonyl groups. One technique used was Doebner reaction and the other technique used was Claisen-Schmidt reaction. Therefore the aim of this experiment is to synthesize trans p-methoxycinnamic acid and to synthesize dibenzalacetone via an aldol condensation reaction between acetone and benzaldehyde. The products would be recrystallized using ethanol
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