Mix thoroughly. The flask was swirled to produce a homogeneous yellow solution. (ii)To synthesize alcohol from aldehyde by NaBH4 reduction. In addition, underage drinking contributes to a range of acute consequences, including injuries, sexual assaults, and even deaths. C. Reaction of Phenols Equation 97,000 students between the ages of 18 and 24 report experiencing alcohol-related sexual assault or date rape. (CH3) 2CHOH + HCl (CH3) 2CHCl + ZnC2 + H2O In this experiment, the benzil (diketone) is used as the organic substrate. This lab report recaps the procedure and results of the lab. Reduction describes the gain of electrons or decrease in oxidation state of an atom, ion or molecule. Ok, so down to business. Ethyl Alcohol Date Submitted: March 06, 2015 Benzyl Alcohol The suffix -ol appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority; in substances where a higher priority group is present the prefix hydroxy- will appear in the IUPAC name. Add potassium dichromate solution to each of the test tube. Using the color-coded syringe provided in the hood, add 2 mL of 1 M NaOH to the vanillin in the conical vial. ALCOHOLS, ETHERS, AND PHENOLS 2(CH3)2CHOH + KMnO4 2(CH3) 2CO + 2H2O + MnO2 + K+ The reductant is also called an electron donor as it donates electrons. Introduction: 2. In everyday life "alcohol" without qualification usually refers to ethanol, or a beverage based on ethanol (as in the term... ... A. Lucas Test In order for the reaction to occur and to better control the stereochemistry and yield of the product, the metal hydride nucleophile of the reducing agents such as LiH, LiAlH4, or NaBH4 must be carefully chosen. 696,000 students between the ages of 18 and 24 are assaulted by another student who has been drinking. the alkoxide followed by protonation to form the alcohol. ...Acid Test/ Jones Oxidation 1.95 mmol of NaBH4 was added while the solution was constantly swirled. ...In chemistry, an alcohol is an organic compound in which the hydroxyl functional group (-OH) is bound to a carbon atom. B. Oxidation of Alcohols Observe the change in color of the solution as soon as possible and the time required for such change to occur. But many substances, particularly sugars (examples glucose and sucrose) contain hydroxyl functional groups without using the suffix. Record the weight directly into your notebook to the maximum accuracy of the balance. C6H5CH2OH + HCl + ZnCl2 C6H5CH2Cl +ZnCl2 +H2O Isopropyl Alcohol Please join StudyMode to read the full document. Consequences of Underage Alcohol Use: Research indicates that alcohol use during the teenage years could interfere with normal adolescent brain development and increase the risk of developing an AUD. 3C6H5NO3 + FeCl3 Fe(C6H4NO3) 3 + 3HCl 3. HO H Cyclohexanol MW 100, bp 160 - 1610 dens. Of those, ethanol (C2H5OH) is the type of alcohol found in alcoholic beverages, and in common speech the word alcohol refers specifically to ethanol. 6. 2. = 152.14 g/mole m.p. Equation 11-30-2011 Lab Section 13 Category Entertainment; Show more Show less. The flask was swirled in an ice-water bath for 1-2 minutes and the solution was cooled to approximately 10°C. The purpose of this experiment is to see if vanillin can be synthesized to vanillyl alcohol through reduction with sodium borohydride. ...Sodium borohydride Reduction of Benzil 2.5 mmol of vanillin were dissolved in 2.5 mL of 1 M NaOH solution in a 25 mL Erlenmeyer flask. 2.  Explain why Lucas test is applicable only to alcohols containing 5 or less carbons No reaction Reduction reactions can be determined through three features. Picric Acid Globally, alcohol misuse is the fifth leading risk factor for premature death and disability; among people between the ages of 15 and 49, it is the first. Cool the solution in an ice bath, and add 7 mL of 5% aqueous HCI to repro- tonate the … A change in color of the reagent from orange to green represents a positive test. Balanced equations: Introduction The H- of the NaBH4 reduces one or both carbonyl groups in benzil and then the acidification processes results in a diol or two secondary alcohols as products. Tert-butyl Alcohol Date Performed: February 27, 2015 C6H5CH2OH + KMnO4 C6H5COOH + H2O +MnO2 + K+ 1. The second is the addition of hydrogen to a bond and thirdly, the replacement of a more electronegative atom with carbon or hydrogen. 2.) C4H10O + KMnO4 C4H8O2 + H2O + MnO2 + K+ Procedure In a 50-mL beaker, dissolve vanillin (8.0 mmol, 1.0 g) in 1 M aqueous NaOlå (7 mL). The concentration of vanillin did not increase by prolonging the incubation time, whereas vanillyl alcohol, that was less than 0.05 mM at this time, slightly increased upon incubation. In a small beaker dissolve 12.0 mmol of NaBH4 (FW 37.83 g/mol) in about 6 mL of 1 M NaBH4. Weigh between 2.5 and 2.6 g of vanillin into a 50 mL beaker. The Lucas reagent is an aqueous solution of strong acid... ...Alcohol Facts and statistics ( www.niaaa.nih.gov-2012 ) Global Burden of alcohol abuse, In 2012, 3.3 million deaths, or 5.9 percent of all global deaths (7.6 percent for men and 4 percent for women), were attributable to alcohol consumption.. Alcohol contributes to over 200 diseases and injury-related health conditions, most notably alcohol dependence, liver cirrhosis, cancers, and injuries. Juris Marie G. Garcia CHO OCH OH Vanillin CH20H OCH3 OH Vanillyl alcohol MW 152, mp 81 -83 (a, 4-dihydroxy-3-methoxytoluene) Procedure: Preparation of Vanillyl Alcohol In redox reactions, the reductant (or reducing agent) loses electrons and is oxidized while the oxidant (or oxidizing agent) gains electrons and is reduced. = 152.14 g/mole m.p. HCl was added until the pH of the solution was distinctly acidic to pH paper. Currently I am attempting to reduce vanillin to vanillyl-alcohol and have run into sort of an issue. The agent reduces other substances and so, the agent itself is oxidized. 4) to produce vanillyl alcohol (4-hydroxy-3-methoxybenzyl alcohol), scheme 1. Study Questions: 0.96 g/mL Cyclohexanone MW 98, bp 1552 dens. In 2012, alcohol accounted for 5.1 percent of disability adjusted life years (DALYs) worldwide. C2H5OH + HCl + ZnCl2 C2H5Cl + H2O Fill out your reaction table by calculating the mmol and equivalents of reagents used based on YOUR mass of vanillin. The suffix -ol in non-systematic names (such as paracetamol or cholesterol) also typically indicates that the substance includes a hydroxyl functional group and, so, can be termed an alcohol. Benzyl Alcohol p-Bromophenol Ethyl Alcohol Add NaBH4 (0.13g, mmol) and swirl the flask occasionally for the next 20—30 minutes. Phenol Test Sample = 154.16 g/mole m.p. The chemical process studied in this lab was reduction, the process of reducing the number of bonds to oxygen and increasing the number of bonds to hydrogen. It is mostly used in foods (killer French toast) and perfumes (Ode de Keibler). However, there are many processes that are classed as redox even though no electron transfer occurs, for example those reactions that involves covalent bonds. 11/30/2017 Oscerfolio for Shiny Chen 3/5 A. Vanillin B. Hence, this reaction can be used to distinguish tertiary alcohols form primary and secondary alcohols. What is the principle involved in Chromic acid test? OH O H OCH3 NaBH4 H2O OH OCH3 OH NaOH H3BO4 Vanillin M.W. The solution was allowed to stand undisturbed for 30 minutes at room temperature. The first is a loss of oxygen from a bond or loss of a bond to oxygen as in the case of carbon-oxygen double bond to a carbon-oxygen single bond. Sodium Borohydride C. Water Enter Your Answer: A B C A Correct Question 6 What is the theoretical yield of vanillyl alcohol (in mg)? Cautiously add concentrated sulfuric acid and mix. Reduction of vanillin to vanillyl alcohol. Procedures: Borohydride Reduction of Vanillin to Vanillyl Alcohol After isolating the product, you will determine its melting point, determine the isolated yield of the reaction and discuss how NMR may be used to verify the reaction. Tert-butyl Alcohol Primary alcohols are oxidized by the reagent to carboxylic aicds; secondary alcohols are oxidized to ketones. CMY 211 If only one carbonyl group is reduced, the product results in a racemic mixture of benzoin. After the time period, the flask was cooled in an ice-water bath and 3 M HCl was added dropwise with swirling. Place ethanol, isopropyl alcohol and tert-butyl alcohol in three different test tubes. 3BrC6H5OH + FeCl3 Fe(BrC6H4O) 3 + 3HCl If both carbonyl groups are reduced, the product results in a meso-hydrobenzion or a racemic mixture... ...Megan Entwistle, Maria Amos, and Paul Golubic 1,825 college students between the ages of 18 and 24 die from alcohol-related unintentional injuries, including motor-vehicle crashes. Answers to Questions: p-Nitrophenol Balanced equations: A. Lucas Test Test Sample Equation Ethyl Alcohol C2H5OH + HCl + ZnCl2 C2H5Cl + H2O Isopropyl Alcohol (CH3) 2CHOH + HCl (CH3) 2CHCl + ZnC2 + H2O Tert-butyl Alcohol (CH3) 3COH + HCl + ZnCl2 (CH3) 3CCl + ZnCl2 +H2O Benzyl Alcohol C6H5CH2OH + HCl + ZnCl2 C6H5CH2Cl +ZnCl2 +H2O B. Oxidation of Alcohols Test Sample Equation Ethyl Alcohol C2H5OH + KMnO4 CH3COOH + … Note the odor of the product produced. Being that LiAlH4 and NaBH4 will not react with isolated carbon-carbon double bonds nor the double bonds from aromatic rings; the chosen compound can be reduce selectively when the nucleophile only react with electrophilic carbons. = 82 oC Vanillyl alcohol M.W. Answer: Test Sample 1.) If the mixture does not dissolve after 5 minutes of continuous stirring add another 5 mL NaBH4 and cool the solution to just below 15°C. 4. Vanillin M.W. Redox (shorthand for REDuction-OXidation) reactions are chemical reactions in which the oxidation state (or oxidation number) of atoms has changed. Test Sample You've reached the end of your free preview. C6H5OH + 3Br2 C6H5OHBr3 + 3HBr Figure 1: reduction mechanism for the reaction C6H5OH + KMnO4 C6H4O2 + MnO2 + H2O + K+ An important class of alcohols are the simple acyclic alcohols, the general formula for which is CnH2n+1OH. 3. The Purpose of this experiment is for the students to learn how to use sodium borohydride to reduce benzil to its secondary alcohol product via reduction reaction. Chromic Acid test is a qualitative test used for the oxidation of primary and secondary alcohol to carboxylic acid and ketones, respectively. 0.95 g/mL Alkoxide intermediate In Experiment 24.2 an aldehyde is reduced to a primary alcohol. Diethyl Ether In the balanced equation for the reaction between vanillin and sodium borohydride, X C 8 H 8 O 3 + BH 4-+ 4 H 2 O → Y C 8 H 10 O 3 + H 3 BO 3 + OH-what is the value of the coefficient of vanillin, X? 3. Place 380 mg (0.380 g) of vanillin in a clean 5 mL conical reaction vial containing a spin vane. CHEM 0330 Organic Lab 1 Loading... Autoplay When autoplay is enabled, a suggested video will automatically play next. 3C10H7OH + FeCl3 Fe(C10H7O)3 + 3HCl This two-step reaction reduces aldehydes by hydrides to primary alcohols, and ketones to secondary alcohols. Rank the alcohols based on the 1-fastest and 3-slowest/no reaction. 5. = 82 oC Vanillyl alcohol The overall, balanced equation for this reaction is given in equation (3); it is balanced with respect to the key reactants, vanillin, 1, and sodium borohydride, and the product, vanillyl alcohol, 2. Label them accordingly. Procedure(Please refer to the detailed instructions on lab 12 handout)Physical Quantity TableType of substanceMolecular FormulaMolecular Weight (g/mol)Density(g/cm3)Melting Point(oC)Boiling Point(oC)HazardO-vanillinC8H8O3152.15-42.5265-266Harmful andIrritantFor all 3vanillinC8H8O3152.151.05680-81285isovanillinC8H8O3152.15-113-115179Vanillyl alcohol*C8H10O3154.17-113-115--Sodium hydroxide**NaOH39.992.13181390CorrosiveHydrochloric acidHCl36.461.18-26110CorrosiveSodium borohydrideNaBH437.831.074505400IrritantCorrosive*Vanillyl alcohol is soluble in cold organic solvents such as ether/alcohol and hot water, but insoluble in cold water.
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