ipl-logo

Carbonylcyclohexanone Lab Report

1013 Words5 Pages

Experiment 7A: Carbonyl Reduction: Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone Experiment 7A, Carbonyl Reduction: Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone, provides firsthand experience with carbonyl reductions. NaBH4, a mild reducing agent, was used to reduce the ketone functional group in the compound, 4-tert-Butylcyclohexanone, that was then protonated using hydrochloric acid to produce two diastereomers (cis/trans) of 4-tertbutylcyclohexanol. Moreover, this experiment refined skills in using H-NMRs (integration, multiplicity, and coupling constants) to effectively distinguish between cis and trans isomers of a desired product. To begin the experiment, 50 mg of 4-t-butylcyclohexanone and methanol were added to a conical vial. NaBH4 was then added to the reaction mixture to reduce the ketone functional group (present in the starting material). The reaction was allowed to proceed for 30 minutes and was subsequently quenched using hydrochloric acid. The addition of hydrochloric acid permitted the protonation of the reduced ketone (O-) to form the two diastereomer …show more content…

Cis-isomers have a dihedral angle of 90˚ resulting in a relatively low coupling constant and low splitting. Trans-isomers have a dihedral angle of 180˚ producing a relatively high coupling constant indicating increased splitting. Thus, the two compounds were also distinguished based on the observed splitting of the two peaks. With respect to a Newman projection for the C1-C2 bond of each product, the relative splitting was determined. For the trans-product the Newman projection exhibited a dihedral angle of 60˚ between H1 and H2, while H1 and H2’ exhibited a dihedral angle of 180˚. The H1 single was therefore split into a triplet of triplets by two different groups of hydrogens. https://www.odinity.com/hydride-reduction-reactions-stereoselective-adventure/ Trans C1-C2 Trans

Show More
Related
382 Words | 2 Pages

The purpose of this experiment was to learn about metal hydride reduction reactions. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. Reduction of an organic molecule usually corresponds to decreasing its oxygen content or increasing its hydrogen content. In order to achieve such a chemical change, sodium borohydride (NaBH4) is used as a reducing agent. There are other metal hydrides used in the reduction of carbonyl groups such as lithium aluminum hydride (LiAlH4).

Read More
904 Words | 4 Pages

Chem 51 LB Experiment 3 Report Scaffold: Bromination of Trans-Cinnamic Acid 1. The goal of this experiment was to perform a halogenation reaction through the addition of two bromides from pyridinium tribromide. This was accomplished by reacting trans-cinnamic acid with pyridinium tribromide. After the reaction took place, melting point analysis was conducted to find out the stereochemistry of the product, which could either be syn-addition, anti-addition, or syn + anti-addition. 2.

Read More
1039 Words | 5 Pages

Experiment 2 Report Scaffold (Substitution Reactions, Purification, and Identification) Purpose/Introduction 1. A Sn2 reaction was conducted; this involved benzyl bromide, sodium hydroxide, an unknown compound and ethanol through reflux technique, mel-temp recordings, recrystallization, and analysis of TLC plates. 2. There was one unknown compound in the reaction that was later discovered after a series of techniques described above.

Read More
1399 Words | 6 Pages

It is understood the mechanism is acid-catalyzed where protons coordinate with the carbonyl oxygen to make the carbonyl carbon more electropositive for nucleophilic attack (Scheme 1). In the experimental procedure all reactants were added together, this is inefficient as the protons can coordinate with either trans-cinnamic acid or methanol. Coordination with methanol is unnecessary as it reduces its nucleophilicity and makes less protons available to coordinate with the carboxylic acid. To improve

Read More
967 Words | 4 Pages

Dehydration of 2-Methylcyclohexanol Sura Abedali Wednesday 2:00 PM January 31, 2018 Introduction: Dehydration reactions are important processes to convert alcohols into alkenes. It is a type of elimination reaction that removes an “-OH” group from one carbon molecule and a hydrogen from a neighboring carbon, thus releasing them as a water molecule (H2O) and forming a pi bond between the two carbons1. In this experiment, 2-methylcyclohexanol undergoes dehydration to form three possible products: methylenecylcohexane, 1-methylcyclohexene, and 3-methylcyclohexene in a Hickman still apparatus. Adding 85% Phosphoric Acid to protonates the “-OH” group, turning it into a better leaving group and initiating the dehydration reaction.

Read More
367 Words | 2 Pages

In this case, a hydride shift will occur between the hydrogen attached to the charge and the hydrogen near the methyl group. The result is a tertiary carbocation and a double bond will form near the substituent; the alkene with the most substituted group is the major product, or 1-methylcyclohexene. According to Zaitsev’s rule, the alkene with the most substituted group would be the major product, because it is the most stable. The formation of the tertiary carbocation could also produce the third product, though in less quantity because it forms a less substituted alkene (minor product). In order to proceed with this reaction, 2-methylcyclohexanol is combined with the acids, phosphoric and sulfuric acid, and heated under distillation.

Read More
452 Words | 2 Pages

In this experiment, racemic 2-methylcyclohexanone was reduced using sodium borohydride as a nucleophile to give a diastereomeric mixture of cis and trans secondary alcohols. The products were analyzed for purity using IR spectroscopy and gas chromatography. 1.2 g of 2-methylcyclohexanone and 10 mL of methanol were combined in a flask and cooled in an ice bath. Two 100 mg portions of sodium borohydride were added to the flask and stirred. 5 mL of 3M sodium hydroxide, 5 mL of de-ionized water, and 15 mL of hexane were added to the reaction flask and stirred.

Read More
973 Words | 4 Pages

Results and discussion Stirring of L with 4-methylaniline and 4-methoxyaniline in equimolar proportion in water at room temperature for 72 h without any Lewis acid catalyst gives L.H2O and L respectively (Scheme 1). The yield of L.H2O is 90% and that of L 70%. These are obtained in 60% yield when the reactants are refluxed in water for 14 h. But the yield goes on decreasing when increasingly more refluxing time is used. Earlier Moody et al have [5] studied opening of the epoxide ring in L in connection with their total synthesis of the pentacyclic marine alkaloid ascididemin from 1,10-phenanthroline (phen).

Read More
391 Words | 2 Pages

The objective of this experiment was to use an aldol condensation reaction to synthesize 3-nitrochalcone from 3- nitrobenzaldehyde. This was accomplished with a Diels-Alder reaction that utilized 3-nitrobenzaldehyde, acetophenone, ethanol, and sodium hydroxide. The mechanism for the synthesis of 3-nitrochalcone is presented in Figures 1 and 2. The alpha carbon on the acetophenone is deprotonated. This is followed by the attack of the alpha carbon anion on the carbonyl carbon on the 3-nitrobenzaldehyde.

Read More
1479 Words | 6 Pages

There are numerous ways for the synthesis of organic esters and most of which have been briefly studied by Yadav and Mehta 7. The simple and old route for preparing esters is by the reaction

Read More
1234 Words | 5 Pages

To further evaluate the binding regions within the binding site, an aromatic CH probe was used to locate hydrophobic regions (Patrick, 2013, p. 407). It was found that the pteridine ring of CB 3717 formed its hydrogen bond within a hydrophobic region. Based on this, the researchers determined that a naphthalene ring could be a reasonable replacement for the pteridine group, with ample room to include a substituent that could recreate the hydrogen bonding

Read More
2059 Words | 9 Pages

The Journal of Organic Chemistry, 1996. 61(16): p. 5400-5405. 7. Keck, G.E., Directed Reduction of β-Amino Ketones to Syn or Anti 1,3-Amino Alcohol Derivatives.

Read More
838 Words | 4 Pages

Cross Condensation of aldol 2015007632 Dowrie, K Contents Reaction 1 Introduction 1 Experiment Procedure 2 Experimental results 3 Table of calculations 3 Calculations 3 NMR 4 TLC 4 References 5 Reaction Introduction An aldehyde reaction is when aldehydes and keytones, both containing an α-hydrogen in the presence of an alkali group condenses and forms an enone. Acetone has α-hydrogens on each side. The proton can be removed and therefore giving a nucleophile anion. The aldehyde carbonyl is more reactive than the keytone and so it reacts rapidly with the anion.

Read More
1052 Words | 5 Pages

Introduction Strong acids and strong acids both dissociate completely in water forming ions. However, strong acids donate a proton to form H3O+ along with a conjugate base and strong bases accept a proton to form OH- along with a conjugate acid. The chemical behavior of acids and bases are opposite. When they are together, their ions cancel out and form a neutral solution. In this experiment, HCl and NaOH will react to form NaOH and H2O with these two steps: The overall reaction is: Both Na+ and Cl- ions combine to form NaCl.

Read More
1148 Words | 5 Pages

Introduction Chevron Phillips Chemical Company is the major producer of Cyclohexane. This successful company hoses the three largest cyclohexane plants in the world. Many are puzzled by how the production of cyclohexane seems to have become stagnant. Perhaps this is due to the cost of benzene increasing or the demand increasing. Through thorough investigation, the answer to this question and many more can be answered.

Read More

More about Carbonylcyclohexanone Lab Report

Open Document