Techniques in organic chemistry mohrig pdf download

Get Organic chemistry laboratory techniques Books now! This book is a hands-on guide for the organic chemist. Focusing on the most reliable and useful reactions, the chapter authors provide the information necessary for a chemist to strategically plan a synthesis, as well as repeat the procedures in the laboratory. Any research that uses new organic chemicals, or ones that are not commercially available, will at some time require the synthesis of such compounds.

Therefore, organic synthesis is important in many areas of both applied and academic research, from chemistry to biology, biochemistry, and materials science. The third edition of. This highly effective and practical manual is designed to be used as a supplementary text for the organic chemistry laboratory course - and with virtually any main text - in which experiments are supplied by the instructor or in which the students work independently. Each technique contains a brief theoretical.

This book presents comprehensive coverage of green chemistry techniques for organic and. The first edition of this book achieved considerable success due to its ease of use and practical approach, and to the clear writing style of the authors. Techniques in Organic Chemistry is the most comprehensive presentation of lab techniques. Organic chemistry experiments even if when a standard laboratory is not available. Wheeler Conover. Recommend Documents. Teaching techniques in the undergraduate organic laboratory.

Laboratory Techniques in Electroanalytical Chemistry, 2nd Edition. Book and Media Review pubs. Your email address will not be published. Eye Wash Stations You should always wear safety goggles while working in a laboratory, but if you accidentally splash something in your eyes, immediately use the eye wash station to rinse them with copious quantities of slightly warm water for 10—15 min. Learn the location of the eye wash stations in your laboratory and examine the instructions on them during the first check-in lab session.

First Aid Kits Your laboratory or a nearby stockroom may contain a basic first aid kit consisting of such items as adhesive bandages, sterile pads, and adhesive tape for treating a small cut or burn. All injuries, no matter how slight, should be reported to your instructor immediately.

Your instructor will indicate the location of the first aid station and instruct you in its use. Personal Safety 1. Think about what you are doing while you are in the laboratory.

Read the experiment before the laboratory session starts and perform laboratory operations with careful forethought. It is a law in many states and common sense in the remainder to wear safety glasses or goggles at all times in the laboratory. Your institution may have a policy regarding wearing contact lenses in the laboratory; learn what it is and follow it. Wear clothing that covers and protects your body.

Shorts, tank tops, and sandals or bare feet are not suitable attire for the lab. Avoid loose clothing and loose long hair, which are fire hazards or could become entangled in an apparatus.

Laboratory aprons or lab coats may be required by your instructor. Precautions When Handling Reagents your hands with soap and water at the end of the laboratory period. Never eat, chew gum, drink beverages, or apply cosmetics in the lab. Be aware of what your neighbors are doing. Many accidents and injuries in the laboratory are caused by other people. Often the person hurt worst in an accident is the one standing next to the place where the accident occurred.

Make yourself aware of the procedures that should be followed in case of any accident. Never work alone in the laboratory. Being alone in a situation in which you may be helpless can be life threatening. Women who are pregnant or who become pregnant should discuss with the appropriate medical professionals the advisability of working in the organic chemistry laboratory.

Never taste, ingest, or sniff directly any chemical. Always use the hood when working with volatile, toxic, or noxious materials. Handle all chemicals carefully, and remember that many chemicals can enter the body through the skin and eyes, as well as through the mouth and lungs. Protective attire.

Wear a lab coat or apron when working with hazardous chemicals. Cotton is the preferred fabric because synthetic fabrics could melt in a fire or undergo a reaction that causes the fabric to adhere to the skin and cause a severe burn. Disposable gloves. Disposable gloves are available in all laboratories. Wear gloves to prevent chemicals from coming into contact with your skin unnecessarily. Table 1. A more extensive chemical resistance table for types of gloves may be posted in your laboratory.

Consult your instructor if you are in doubt about the safe handling procedures for any chemical. If you are handling a particularly hazardous compound, wear the appropriate type of gloves and know what the safe handling procedures for it are before you begin the experiment. Flammable solvents. Use an Erlenmeyer flask fitted with a cork—never an open beaker—for temporarily storing flammable solvents at your work area.

Order in the Laboratory Keep your laboratory space clean and neat. In addition to your own bench area, the balance and chemical dispensing areas should be left clean and orderly. If you spill anything while measuring out your chemicals, notify your instructor and clean it up immediately. After weighing a chemical, replace the cap on the container and dispose of the weighing paper in the appropriate receptacle. Keep gas and water valves closed whenever they are not in use.

Floors can become very slippery if water is spilled; wipe up any spill immediately. Burns and Other Injuries Remember that both glass and the tops of hot plates look the same when hot as when cold. When heating glass, do not touch the hot spot. Do not put hot glass on a bench where someone else might pick it up. Steam and boiling water cause severe burns.

Turn off the steam source before removing containers from the top of a steam bath or steam cone. The screw attached to the rounded handle that controls a steam line can become very hot; be careful not to touch it when you turn the steam on or off. Handle containers of boiling water very carefully. Explosions Never heat a closed system! Also, never completely close off an apparatus in which a gas is being evolved: always provide a vent in order to prevent an explosion.

The first few seconds after an accident may be crucial. Acquaint yourself with the following instructions so that you can be of immediate assistance. Fire Your laboratory instructor will inform you on the first day of lab about the proper response to a fire. It is important to know the policy of your institution concerning when to evacuate the building and when to use a fire extinguisher. In case of a fire in the lab, get out of danger and then immediately notify your instructor.

If possible, remove any containers of flammable solvents from the fire area. Know the location of the fire extinguishers and how they operate. A fire extinguisher will always be available. If you use one, aim low and direct its nozzle first toward the edge of the fire and then toward the middle. Tap water is not always useful for extinguishing chemical fires and can actually make some fires worse, so always use the fire extinguisher.

Be sure you know where the fire blanket and safety showers are located. If your clothing is on fire, do not run. Rapid movement fans flames. General Policy Regarding Accidents Always inform your instructor immediately of any accident that happens to you or your neighbors. Minor Cuts and Burns Learn the location of the first aid kit and the materials it contains for the treatment of simple cuts and burns.

Notify your instructor immediately if you are cut or burned or if any chemical is spilled on your skin. Seek immediate medical attention for anything except the most trivial cut or burn. Press on the cut to help slow the bleeding. Apply a bandage when the bleeding has ceased. If the cut is large or deep, seek immediate medical attention. Heat burns. Apply cold water for 10—15 min to any heat burn. Seek immediate medical attention for any extensive burn. Chemical burns.

The first thing to do if any chemical is spilled on your skin, unless you have been specifically told otherwise, is to wash the area well with water for 10—15 min. This treatment will rinse away the excess chemical reagent. For acids, bases, and toxic chemicals, thorough washing with water will save pain later.

Specific treatments for chemical burns are published in The Merck Index. Seek immediate medical treatment for any serious chemical burn. Chemical splash in the eyes.

If a chemical gets into your eyes, immediately go to the eye wash station and wash your eyes with a copious amount of slightly warm water.

Position your head so that the stream of water from the eye wash fountain is directed at your eyes. Hold your eyes open to allow the water to flush the eyeballs for 10—15 minutes. Because this position is difficult, assistance may be required.

Do not hesitate to call for help. Do not use very cold water because it can damage the eyeballs. Seek medical treatment immediately after using the eye wash for any chemical splash in the eyes.

If you are wearing contact lenses, they must be removed for the use of an eye wash station to be effective, an operation that is extremely difficult if a chemical is causing severe discomfort to your eyes. Therefore, it is prudent not to wear contact lenses in the laboratory. A major concern in chemical toxicology is quantity or dosage. It is important that you understand how toxic compounds can be handled safely in the organic laboratory.

The toxicity of a compound refers to its ability to produce injury once it reaches a susceptible site in the body. What is toxic for people may not be toxic for other animals and vice versa.

A substance is acutely toxic if it causes a toxic effect in a short time; it is chronically toxic if it causes toxic effects with repeated exposures over a long duration. Fortunately, not all toxic substances that accidentally enter the body reach a site where they can be deleterious.

Even though a toxic substance is absorbed, it is often excreted rapidly. Our body protects us with various devices: the nose, scavenger cells, metabolism, and rapid exchange of good air for bad. Many foreign substances are detoxified and discharged from the body very quickly.

Action of Toxic Substances on the Body Although many substances are toxic to the entire system arsenic, for example , many others are site specific. In some cases, the metabolites of a compound are more toxic than the original compound.

An example is methanol poisoning. As far as the body is concerned, it does not matter whether the toxicity is due to the original substance or to a metabolic product of it. Toxicity Testing and Reporting 1. Other tests include dermal toxicity skin sensitization and irritation of the mucous membranes eyes and nose. The Merck Index is a useful reference for the toxicity of organic compounds and lists the LD50 of many compounds. The toxicity of virtually all chemical compounds that are commercially available has been reported, and every year the toxicities of many more compounds become known.

Chemists and biologists have learned a great deal about toxicities in the past few decades. A wall chart of toxicities for many common organic compounds may be hanging in your laboratory or near your stockroom.

Every MSDS contains information on a list of topics required by law that describe the physical properties, hazards, safe handling and storage practices, and first aid information for the chemical. Manufacturers are required to prepare an MSDS for every chemical sold; the content is the same for a specific chemical, but the format in which the information is presented differs from one company to another.

An MSDS from one company may be easy to read while that from another may be more difficult to understand. MSDS information for thousands of compounds can be obtained easily on the Internet. Reproduced with permission from The Merck Index, Fourteenth edition. All rights reserved. The entry for sec-butyl acetate lists the caution information at the end Figure 1. Hazardous Materials Identification Systems The labels on chemical containers carry warnings about the hazards involved in handling and shipping the compounds.

The four-diamond symbol and a globally harmonized system of pictograms are the most commonly used hazardous materials identification systems. Four-diamond symbol. Chemical suppliers put a color-coded, fourdiamond symbol—developed by the National Fire Protection Association—on the container label of all reagents they sell Figure 1.

The four diamonds provide information on the hazards associated with handling the compounds: fire hazard top, red diamond reactivity hazard right, yellow diamond specific hazard bottom, white diamond health hazard left, blue diamond Fire hazard red FIGURE 1.

The symbol in the specific hazard diamond indicates that the compound is reactive with water and should not come into contact with it. Explosive Oxidizing Highly flammable or extremely flammable Toxic or very toxic Harmful or irritant Corrosive Biohazard Dangerous for the environment The numerical values in the diamonds range from 0 to 4—0 indicates no chemical hazard and 4 indicates extreme chemical hazard.

Many chemical suppliers also indicate hazards by printing the universally understandable pictograms approved at the UN-sponsored Rio Earth Summit in on the labels of their reagents Figure 1. Since then the pictograms have become a widely accepted standard on chemical labels around the world. Other warnings found on chemical labels. Lachrymator: Substance causes irritation and watering of the eyes tears. Cancer suspect agent: Substance is carcinogenic in experimental animals at certain dose levels, by certain routes of administration, or by certain mechanisms considered relevant to human exposure.

Available epidemiological data do not confirm an increased cancer risk in exposed humans. Mutagen: Substance induces genetic changes. Teratogen: Substance induces defects in a developing fetus.

Furr, A. Lewis, Sr. Rapid Guide to Hazardous Chemicals in the Workplace; 4th ed. Every person working in a laboratory must also be aware of the impact that he or she has on the environment.

Before disposing of anything in the lab, you should be conscious of how the disposal will affect the environment. Although zero waste is impossible, minimum waste is essential. Industries are now required to account for almost every gas, liquid, or solid waste they put into the environment. In the undergraduate laboratory, we should do the same. Reduce energy requirements. Utilize renewable resources whenever possible.

Minimize or prevent the formation of waste. The goal of green chemistry is to be as environmentally friendly as possible in the synthesis and utilization of chemicals both in the laboratory and in industrial and manufacturing applications. How can an existing chemistry procedure be changed to one that could be called green chemistry?

The first step is to ascertain the safety information on the reagents and solvents that are currently being used, as well as information on any toxic by-products that would remain after completion of the reaction. The next steps are to consider what would be safer, less toxic alternatives for the reactants and solvents and to ascertain whether another method would give the desired product using less hazardous materials.

For example, consider replacement solvents that pose fewer health and environmental hazards. Water In the quest for solvents that minimize health hazards and risks to the environment, water would appear to be ideal because it is readily available and nonhazardous. But a requirement for most reaction solvents is that they dissolve the reagents used in the reaction, and a very large percentage of organic compounds are insoluble or only slightly soluble in water.

However, reactions in aqueous solutions can be promoted in several ways with water-insoluble organic compounds, such as using vigorous stirring or phase-transfer catalysts.

Solid CO2 dry ice sublimes, or vaporizes, from the solid to gaseous state without melting. When CO2 is subjected to conditions of temperature and pressure that exceed its critical point, A fluid above its criticalpoint temperature and pressure is called a supercritical fluid. Supercritical CO2 is a very good solvent with properties similar to many common organic solvents.

The high-pressure equipment necessary to contain supercritical CO2, however, makes its use in academic laboratories impractical. Supercritical CO2 can replace traditional and hazardous solvents in industrial-scale chemical processes, include decaffeinating coffee, dry-cleaning clothing, cleaning electronic and industrial parts, and chemical reactions. At the end of these processes, the pressure is released and the escaping CO2 gas can be easily recovered and recycled.

Example 1. Extraction of an Organic Compound from an Aqueous Mixture The organic chemist frequently needs to separate an organic compound from an aqueous mixture using the process of extraction, in which the higher solubility of the organic compound in an organic solvent selectively transfers it from an aqueous mixture. Consider a procedure that specifies dichloromethane as a solvent for extracting caffeine from tea leaves. Safety information. The safety information on the MSDS for dichloromethane indicates that the compound is a cancer suspect agent, toxic, a neurological hazard, and an irritant to the skin, eyes, and mucous membranes.

The MSDS for ethyl acetate states that it is an irritant to the skin, eyes, and mucous membranes. Ethyl acetate certainly looks safer. Relative volatilities of dichloromethane and ethyl acetate. However, the higher boiling point of ethyl acetate means that it requires more heat energy to remove the solvent and recover the caffeine than would dichloromethane.

Solubility of water in the extraction solvent. For an extraction to be successful, the organic solvent and the aqueous phase must have a low solubility in one another.

The solubility of water in ethyl acetate is five times greater than its solubility in dichloromethane. If we want to substitute ethyl acetate for dichloromethane as the extraction solvent, we need a way to decrease the solubility of water in ethyl acetate.

The decrease can be accomplished by saturating the caffeinecontaining aqueous mixture with sodium chloride, which reduces the amount of water that dissolves in ethyl acetate. Relative costs of waste disposal. What happens to the solvent when the extraction of caffeine from tea is completed? It can be removed and recovered from the caffeine by distillation and possibly recycled for use in another application, but eventually the solvent becomes a waste that requires disposal either by burning in a process where the heat energy is recovered or by incineration where the heat is not recovered.

Complete combustion of ethyl acetate produces carbon dioxide and water, whereas complete combustion of dichloromethane produces carbon dioxide, water, and hydrogen chloride. The HCl needs to be removed from the combustion gases before they are released to the atmosphere, a process that increases the disposal costs for chlorinated compounds relative to nonhalogenated compounds.

Justification for the substitution of ethyl acetate for dichloromethane. Using ethyl acetate instead of dichloromethane is less hazardous both to the person doing the procedure and to the environment. In addition, lower waste disposal costs make substitution of ethyl acetate a greener alternative than dichloromethane as the extraction solvent, despite the higher energy costs incurred with ethyl acetate. Example 2. In addition, at the end of the reaction an equivalent amount of chromium III oxide is present as a by-product, requiring expensive disposal to prevent it from becoming an environmental contaminant.

Household bleach, a 5. The oxidation of cyclohexanol with aqueous sodium hypochlorite solution in the presence of acetic acid is an example of green chemistry oxidation. Cyclohexanol is a liquid at room temperature and is relatively insoluble in water. The water in the sodium hypochlorite solution provides the reaction medium. Elimination of the extraction solvent.

Cyclohexanone has traditionally been recovered from the two-phase reaction mixture by extraction with an organic solvent, such as diethyl ether. Steam distillation codistillation of the organic compound with water is a green alternative for separating the cyclohexanone from the inorganic salts in the aqueous reaction mixture. Nonhazardous by-products.

This synthesis also qualifies as green chemistry because the by-products of the reaction, water and sodium chloride, are nonhazardous wastes that can be washed down the sink. Any excess acetic acid remaining in the aqueous solution can be neutralized with sodium carbonate to form acetate ion, also a nonhazardous waste that can be washed down the sink. Example 3. Biochemical Catalysis Biochemical catalysis is a green alternative to traditional catalysis in organic synthesis.

Using thiamine vitamin B1 is a green alternative to using potassium cyanide KCN , the traditional catalyst in the condensation of two benzaldehyde molecules to form benzoin. Laboratory Experiments in Organic Chemistry; 2nd ed. Its contact with acids produces highly toxic hydrogen cyanide gas. Vitamin B1, in the form of thiamine, provides a far safer catalytic reagent for this reaction and eliminates the hazards and waste disposal costs of potassium cyanide.

Thiamine is a naturally occurring compound and a renewable resource. The MSDS for thiamine indicates that it may be harmful when ingested in high concentrations, and it may cause allergic reactions. Overview of Greening a Chemical Process 2. They are part of a continuing effort toward the goal of green chemistry—using chemistry in the synthesis and utilization of chemicals in as environmentally friendly a manner as possible.

New manufacturing processes and chemical syntheses using green chemistry are being developed every day. Fewer Reaction By-Products In addition to finding greener alternatives for solvents and reagents, green chemistry is about finding ways to minimize or eliminate waste by generating fewer by-products in chemical reactions. Chemists generally regard the percentage yield of a chemical reaction as the measure of its success.

However, the percentage yield does not indicate how much mass of the original reagents remains as by-products at the end of the reaction. Atom Economy The concept of atom economy was developed as a quantitative measure of how efficiently atoms of the starting materials and reagents are incorporated into the desired product. The balanced equation for the reaction is used in the calculation of atom economy. Consider the synthesis of 1-ethoxybutane, a substitution reaction in which an ethoxy group replaces the bromine atom of 1-bromobutane.

Science , , — Addition reactions are inherently high in atom economy because both reagents in the reaction are incorporated into the product. The Diels-Alder reaction is an example of an addition reaction. Reaction Efficiency The concept of reaction efficiency was developed as a measure of the mass of reactant atoms actually contained in the final product.

One goal of green chemistry is to design synthetic pathways that improve both the atom economy of a reaction and the percentage yield in order to minimize the waste produced by chemical reactions. Please note the delivery estimate is greater than 3 business days. Free shipping. Skip to main content. Email to friends Share on Facebook - opens in a new window or tab Share on Twitter - opens in a new window or tab Share on Pinterest - opens in a new window or tab.

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