more readily it will depart the molecule. Carbocation: A carbon with only 6 shared valence shell electrons. A full positive charge resides on the carbon. Carbocations are electrophiles. Nucleophile: An atom or assemblage of atoms which will donate electrons to form a new covalent bond. Strong nucleophiles are strong Lewis bases. Electrophile: An atom which will accept electrons and form a
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Title: Reaction of Iodoethane with Sodium Saccharin- Ambient Nucleophile Dates Performed: February 21 + 28‚ 2013 Date Submitted: March 14‚ 2013 Abstract: The product ratio of N-ethylsaccharin to O-ethylsaccharin that occurred due to alkylation with iodoethane at 80 oC was determined to be 81.5% to 18.5%‚ respectively‚ based on an analysis of the 1H NMR spectrum that was collected. The melting point range of 87.8-94.7 oC also indicated that the mixture was largely composed of N-ethylsaccharin
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electron transfer between the carbonyl group and the grignard reagent. Once the Grignard reagent is synthesized it can work as a base by abstracting a proton or it can work as a good nucleophile. When it works as a base it can be added to water‚ alcohols‚ amines‚ acids‚ terminal alkynes and etc. When it works as a nucleophile‚ its nucleophilicity reacts with the electrophilic carbon in a carbonyl group forming a new carbon-carbon bond. Grignard reagents when synthesized are very reactive and thus must
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bromobenzene produces and unstable carbocation. Bromocyclohexane This reacted in 10 seconds because bromocyclohexane is secondary bromine‚ and has steric strain‚ since it is a cyclic compound. The bigger steric in a molecule‚ the harder it is for the nucleophile to attack the leaving group (-Br) from the opposite sides‚ therefore‚ SN2 reaction is slower than SN1 for bromocyclohexane Bromocyclopentane This reacted instantly because bromocyclopentane is secondary bromine‚ and have bigger steric strain
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ethanamine. CH3CH2Br + 2NH3 Reaction of haloalkane with with Sodium Hydroxide (NaOH) Will form alcohol and OHˉion is the nucleophile. Example‚ bromoethane (CH3CH2Br) react with aqueous NaOH and produce (CH3CH2OH) butanol Reaction of haloalkane with Potassium Cyanide (KCN) Produce alkanenitriles RCN and CNˉion‚ cyanide is the nucleophile. Example‚ bromoethane (CH3CH2Br react with KCN and produce (CH3CH2CN) propanenitrile Nucleophilic Substitution of Haloalkanes
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Lab 3: Grignard Synthesis Objective: The goal of this lab is to synthesize a Grignard reagent from bromobenzene and magnesium metal in diethyl ether. This same Grignard reagent would then be used to prepare a tertiary alcohol and then purify and characterize the product. Table of Reagents: Name Chemical formula Melting Point Boiling Point Density Safety Hazards Diethyl ether C4H10O -116.3°C 34.6°C 0.7134 g/ml Flammable Bromobenzene C6H5Br -30.6°C 156°C 1.5 g/ml
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SN2 reaction occurs in a single step. The nucleophile simultaneously attaches to the substrate as the leaving group leaves. The reaction displays second-order kinetics; its rate is proportional to the concentrations of the both the substrate and the nucleophile. In a SN1 reaction‚ the first step is departure of the leaving group from the substrate to form a carbocation(rate-determing); the second step the carbocation rapidly attacked by a nucleophile.
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reactions involve an atom or atoms are replacing one another atom. Many of these reactions require a nucleophile. Nucleophiles have unshared pair of electrons. Weak bases are considered good living groups in Nucleophilic substitution reactions. There are two mechanisms for these reactions are SN1 and SN2.
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The SN2 reaction requires three qualities: a strong nucleophile‚ a good‚ unhindered leaving group‚ and a polar‚ aprotic solvent. For our reaction‚ we have all three bases covered. The nucleophile is an alkoxide‚ a deprotonated alcohol. Technically‚ because our alcohol is a phenol‚ the conjugate base is called a phenoxide. Phenol itself has a pKa of about 10‚ but our alcohol has more resonance opportunities‚ so the pKa is down around 8. This is sufficiently acidic for use of weak base like K2CO3 for
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solvents such as water and ethanol result in bulky solvation shells around the charged nucleophile; this is what reduces its nucleophilic strength. The result is a slower reaction. Polar aprotic solvents do not solvate the nucleophile very strongly‚ this results in an attack on the substrate. Therefore‚ polar aprotic solvents accelerate the rates of reaction‚ especially SN2 reactions‚ where the strength of the nucleophile determines the rate of reaction. As far as the reaction properties are concerned
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