Grignard Synthesis of Tirphenylmethanol David Szuminsky Organic Chemistry Lab II Shaopeng Zhang Monday 1PM 2/10/14 & 2/24/14 - Abstract A sample of triphenylmethanol was prepared using Grignard synthesis techniques. Reflux was used in order to speed up the reaction and the final product was purified using recrystallization methods. The percent recovery and percent yield were 80.46% and 47.526%‚ respectively. A melting point range of 85-87oC was obtained from
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Wittig Reaction and Photoisomerization Abstract: For this laboratory experiment stilbene was produced through a Wittig reaction with benzyltriphenyl phosphonium and benzaldehyde producing a form of stilbene (Figure 1). This reaction favored a crude Z-Stilbene crystal product over its E counterpart. When Z-Stilbene underwent photoisomerization with iodine for 1 hour it reconfigured almost exclusively into its more stable counterpart E-Stilbene. The reaction produced very low yield of 6.3% due
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Radical Cations•+: Generation‚ Reactivity‚ Stability R A R A MacMillan Group Meeting 4-27-11 by Anthony Casarez Three Main Modes to Generate Radical Cations Chemical oxidation D A D A Photoinduced electron transfer (PET) h! 1) D A D A* D A 2) D A h! D* A D A Electrochemical oxidation (anodic oxidation) D Anode D Chemical Oxidation Stoichiometric oxidant: SET O N Bn H N Me O N Me t-Bu
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Preparation u Alcohols when heated in presence of H2SO4‚ H3PO4‚ P2O5‚ Al2O3 or BF3 undergo loss of water molecule with the formation of alkene. Conc. H2SO4 180oC H3PO4/P2O5 200oC Al2O3/BF3 350oC CH3-CH=CH2 + H2O CH3-CH2-CH2-OH CH3-CH=CH2 + H2O CH3-CH=CH2 + H2O u u Mechanism: In the first step OH group of the alcohol is protonated in a fast reversible reaction. Unlike OH group‚ protonated OH group is a good leaving group. Step 1: CH3 CH3-C-CH3 + H+ HO CH3 CH3-C-CH3 H2O+
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one atom contains a negative charge and another atom holds a positive charge. Both the positive and negative charges are contained on the same molecule. When an α-diazocarbonyl compound reacts with an aldehyde or ketone‚ the carbonyl acts as a nucleophile and will attack the electron-deficient carbene centre [7]. This will form an ylide. In the α-diazocarbonyl compound‚ the carbonyl carbon is negatively polarised due to the N2
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Multistep Synthesis of Tetraphenylcyclopentadienone Author: Instructor: Date work performed: 10.18.2012--10.25.2012 Date work submitted: 11.01.2012 Abstract: The aim of this experiment was to perform a multistep synthesis to form tetraphenylcyclopentadienone. The first step of the reactions was to synthesize benzoin from the condensation of benzaldehyde. A yield of 28.91% benzoin was obtained. The MP of benzoin was 127O-130O C and the IR spectra displayed a carbonyl peak at 3415 cm-1
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tubes which contained the same amount of enzyme to substrate were tested for reaction rate with pHs ranging from 4 to 9 as the only difference‚ in order to determine what the optimum pH was. According to previous experiments‚ protenation of the nucleophile limits catalysis at low pH‚ and deprotenation of the hydrogen donor limits it at high pH (Nielsen‚ Vriend & Borchert‚ 2001). In addition‚ a review paper states alpha-amylase
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expensive as Oxone and leaves behind the epoxide plus m-chlorobenzoic acid while Oxone creates non-toxic byproducts and recycles acetone in the epoxidation reaction. Introduction The epoxidation of an alkene creates an epoxide that is reactive to nucleophiles. This is important in organic chemistry as well as biological sciences. For example epoxide hydrolase aids in purification during drug metabolism. The mechanisms for Oxone and mCPBA epoxidation can be found in figures 1 and 2 below. Figure
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Chapter 17—Alcohols and Phenols SHORT ANSWER Drawing Instructions: Draw structures corresponding to each of the given names. 1. Draw: cis-4-tert-butylcyclohexanol ANS: 2. Draw: 3-methyl-2-buten-1-ol ANS: 3. Draw: 2-phenyl-2-propanol ANS: 4. Draw: glycerol ANS: 5. Draw: 2‚ 4‚ 6-trinitrophenol ANS: IUPAC Naming Instructions: Provide proper IUPAC names. 6. Name: ANS: (E)-2-ethylbut-2-en-1-ol 7. Name: HOCH2CH2OH ANS:
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salt by reaction with sodium hydride or lithium diisopropylamide (LDA) + Na H – Sodium hydride [ ( CH3 ) 2 CH] 2 N – Li + Lithium diisopropylamide (LDA) Alkylation of Acetylides Acetylide anions are both strong bases and good nucleophiles They undergo nucleophilic displacement reactions with alkyl halides to form new C-C bonds to alkyl groups; that is‚ they undergo alkylation
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