In organic reactions that occur in the cytosolic region of a cell, the solvent is of course water. In fact, the added salt does dissolve, as represented by the forward direction of the dissolution equation. Small alcohols are completely soluble in water; mixing the two in any proportion generates a single solution. (b) Divers receive hyperbaric oxygen therapy. Hydrogen bonds are much stronger than these, and therefore it takes more energy to separate alcohol molecules than it does to separate alkane molecules. \end{align*}\]. The first substance is table salt, or sodium chloride. Consequently, tremendous quantities of dissolved CO2 were released, and the colorless gas, which is denser than air, flowed down the valley below the lake and suffocated humans and animals living in the valley. interactive 3D image of a membrane phospholipid (BioTopics). %PDF-1.3 The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Intermolecular Forces in NH3 The water solubility of the lower-molecular-weight alcohols is pronounced and is understood readily as the result of hydrogen bonding with water molecules: In methanol, the hydroxyl group accounts for almost half of the weight of the molecule, and it is not surprising that the substance is completely soluble in water. In order to mix the two, the hydrogen bonds between water molecules and the hydrogen bonds between ethanol molecules must be broken. Since the resonance stabilization of the phenolate conjugate base is much greater than the stabilization of phenol itself, the acidity of phenol relative to cyclohexanol is increased. Decompression sickness (DCS), or the bends, is an effect of the increased pressure of the air inhaled by scuba divers when swimming underwater at considerable depths. In an earlier module of this chapter, the effect of intermolecular attractive forces on solution formation was discussed. Indeed, the physical properties of higher-molecular-weight alcohols are very similar to those of the corresponding hydrocarbons (Table 15-1). A.40.8 J B.22.7 kJ C.40.8 kJ D.2,400 J E.2.2 kJ 7.Identify the dominant (strongest) type of intermolecular force present in Cl2(l). 4 0 obj As the length of the alcohol increases, this situation becomes more pronounced, and thus the solubility decreases. Phthalocyanines are potentially promising photosensitizers (PSs) for photodynamic therapy (PDT), but the inherent defects such as aggregation-caused quenching effects and non-specific toxicity severely hinder their further application in PDT. It is able to bond to itself very well through nonpolar (London dispersion) interactions, but it is not able to form significant attractive interactions with the very polar solvent molecules. Students see that even though the only difference between pentanol and pentane is an -OH group, pentanol has basically the same surface tension has decane; This seeming contradiction appears more reasonable when one considers what effect solvation (or the lack of it) has on equilibria expressed by Equation 15-1. ISBN 0-8053-8329-8. In general, the greater the content of charged and polar groups in a molecule, the less soluble it tends to be in solvents such as hexane. Figure \(\PageIndex{2}\): (a) The small bubbles of air in this glass of chilled This is a mathematical statement of Henrys law: The quantity of an ideal gas that dissolves in a definite volume of liquid is directly proportional to the pressure of the gas. Try dissolving benzoic acid crystals in room temperature water you'll find that it is not soluble. Phenol can lose a hydrogen ion because the phenoxide ion formed is stabilised to some extent. =2.8210^{4}\:mol\:L^{1}}\]. This is another factor in deciding whether chemical processes occur. For example, the carbonated beverage in an open container that has not yet gone flat is supersaturated with carbon dioxide gas; given time, the CO2 concentration will decrease until it reaches its equilibrium value. The energy released when these new hydrogen bonds form approximately compensates for the energy needed to break the original interactions. 1-Pentanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Solutions may be prepared in which a solute concentration exceeds its solubility. As a result, there is a significant attraction of one molecule for another that is particularly pronounced in the solid and liquid states. If the ascent is too rapid, the gases escaping from the divers blood may form bubbles that can cause a variety of symptoms ranging from rashes and joint pain to paralysis and death. It is critical for any organic chemist to understand the factors which are involved in the solubility of different molecules in different solvents. For example, it requires 927 kJ to overcome the intramolecular forces and break both OH Figure \(\PageIndex{8}\): Bromine (the deep orange liquid on the left) and water (the clear liquid in the middle) are partially miscible. WebScore: 4.9/5 (71 votes) . If you want to precipitate the benzoic acid back out of solution, you can simply add enough hydrochloric acid to neutralize the solution and reprotonate the carboxylate. How about dimethyl ether, which is a constitutional isomer of ethanol but with an ether rather than an alcohol functional group? As you would almost certainly predict, especially if youve ever inadvertently taken a mouthful of water while swimming in the ocean, this ionic compound dissolves readily in water. Therefore, the air inhaled by a diver while submerged contains gases at the corresponding higher ambient pressure, and the concentrations of the gases dissolved in the divers blood are proportionally higher per Henrys law. They do this by polarization of their bonding electrons, and the bigger the group, the more polarizable it is. However, phenol is sufficiently acidic for it to have recognizably acidic properties - even if it is still a very weak acid. A supersaturated solution is one in which a solutes concentration exceeds its solubilitya nonequilibrium (unstable) condition that will result in solute precipitation when the solution is appropriately perturbed. By this we mean that the equilibrium position for the proton-transfer reaction (Equation 15-1) lies more on the side of ROH and OHe as R is changed from primary to secondary to tertiary; therefore, tert-butyl alcohol is considered less acidic than ethanol: However, in the gas phase the order of acidity is reversed, and the equilibrium position for Equation 15-1 lies increasingly on the side of ROGas R is changed from primary to secondary to tertiary, terf-Butyl alcohol is therefore more acidic than ethanol in the gas phase. (Consider asking yourself which molecule in each pair is dominant?) Dispersion forces increase with molecular weight. Substitution of the hydroxyl hydrogen atom is even more facile with phenols, which are roughly a million times more acidic than equivalent alcohols. Where is hexane found? The chart below shows the boiling points of the following simple primary alcohols with up to 4 carbon atoms: These boiling points are compared with those of the equivalent alkanes (methane to butane) with the same number of carbon atoms. Video \(\PageIndex{4}\): An overview of solubility. However, naked gaseous ions are more stable the larger the associated R groups, probably because the larger R groups can stabilize the charge on the oxygen atom better than the smaller R groups. Even allowing for the increase in disorder, the process becomes less feasible. If the solutes concentration is less than its solubility, the solution is said to be unsaturated. Because water, as a very polar molecule, is able to form many ion-dipole interactions with both the sodium cation and the chloride anion, the energy from which is more than enough to make up for energy required to break up the ion-ion interactions in the salt crystal and some water-water hydrogen bonds. We will learn more about the chemistry of soap-making in a later chapter (section 12.4B). Hint in this context, aniline is basic, phenol is not! Soaps are composed of fatty acids, which are long (typically 18-carbon), hydrophobic hydrocarbon chains with a (charged) carboxylate group on one end. Acids react with the more reactive metals to give hydrogen gas. That means that there will still be a lot of charge around the oxygen which will tend to attract the hydrogen ion back again. (b) A CO2 vent has since been installed to help outgas the lake in a slow, controlled fashion and prevent a similar catastrophe from happening in the future. (Also see Section 11-8A, which deals with the somewhat similar situation encountered with respect to the relative acidities of ethyne and water.). 1-Pentanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. A) 1-pentanol B) 2-pentanol C) 3-pentanol D) 2-methyl-2-pentanol E) 3-methyl-3-pentanol 10) What reagent(s) would you use to accomplish the following conversion? Web1-Pentanol should have larger intermolecular forces due to H- bonding, meaning the molecules are more attracted to each other than in pentane. Layers are formed when we pour immiscible liquids into the same container. 8.2: Solubility and Intermolecular Forces is shared under a CC BY license and was authored, remixed, and/or curated by LibreTexts. The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. The trinitro compound shown at the lower right is a very strong acid called picric acid. Temperature is one such factor, with gas solubility typically decreasing as temperature increases (Figure \(\PageIndex{1}\)). Herein, we synthesized two zinc(II) phthalocyanines (PcSA and PcOA) monosubstituted Legal. The current research deals with the intermolecular interactions of castor oil (biodiesel) as additives to diesel-ethanol (diesohol) fuel blends. In the case of alcohols, hydrogen bonds occur between the partially-positive hydrogen atoms and lone pairs on oxygen atoms of other molecules. qC and the heat of vaporization is 40.7 kJ/mol. The mixture left in the tube will contain sodium phenoxide. Use Henrys law to determine the solubility of this gaseous solute when its pressure is 101.3 kPa (760 torr). Other factors also affect the solubility of a given substance in a given solvent. In aqueous solution, the fatty acid molecules in soaps will spontaneously form micelles, a spherical structure that allows the hydrophobic tails to avoid contact with water and simultaneously form favorable London dispersion contacts. Example \(\PageIndex{1}\): Application of Henrys Law. Legal. stream Select all that apply. At 20 C, the concentration of dissolved oxygen in water exposed to gaseous oxygen at a partial pressure of 101.3 kPa (760 torr) is 1.38 103 mol L1. Is it capable of forming hydrogen bonds with water? The system is said to be at equilibrium when these two reciprocal processes are occurring at equal rates, and so the amount of undissolved and dissolved salt remains constant. ), Virtual Textbook of Organic Chemistry. (Select all that apply) A London dispersion forces (LDFs) B) Dipole-dipole interactions C Hydrogen bonding interactions Now, well try a compound called biphenyl, which, like sodium chloride, is a colorless crystalline substance (the two compounds are readily distinguishable by sight, however the crystals look quite different). (b) The decreased solubility of oxygen in natural waters subjected to thermal pollution can result in large-scale fish kills. Carbonated beverages provide a nice illustration of this relationship. All things have London dispersion forcesthe weakest interactions being temporary dipoles that form by shifting of electrons within a Decreased levels of dissolved oxygen may have serious consequences for the health of the waters ecosystems and, in severe cases, can result in large-scale fish kills (Figure \(\PageIndex{2}\)). WebPentane, hexane and heptane differ only in the length of their carbon chain, and have the same type of intermolecular forces, namely dispersion forces. Some hand warmers, such as the one pictured in Figure \(\PageIndex{10}\), take advantage of this behavior. In the organic laboratory, reactions are often run in nonpolar or slightly polar solvents such as toluene (methylbenzene), hexane, dichloromethane, or diethylether. Alcohols are so weakly acidic that, for normal lab purposes, their acidity can be virtually ignored. Compare the hexane and 1-pentanol molecules. 1. This means that many of the original hydrogen bonds being broken are never replaced by new ones. Now, try dissolving glucose in the water even though it has six carbons just like hexanol, it also has five hydrogen-bonding, hydrophilic hydroxyl groups in addition to a sixth oxygen that is capable of being a hydrogen bond acceptor. { "8.2:_Solubility_and_Intermolecular_Forces_(Problems)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { "8.1:_Heating_Curves_and_Phase_Changes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "8.2:_Solubility_and_Intermolecular_Forces" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "8.3:_Concentrations_of_Solutions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_1:_The_Quantum_World" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_2:_Electrons_in_Atoms" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_3:_Periodic_Patterns" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_4:_Lewis_Structures" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_5:_The_Strength_and_Shape_of_Covalent_Bonds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_6:_Molecular_Polarity" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_7:_Intermolecular_and_Intramolecular_Forces_in_Action" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_8:_Solutions_and_Phase_Changes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "Unit_9:_Semiconductors" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, 8.2: Solubility and Intermolecular Forces, [ "article:topic", "showtoc:no", "license:ccby" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FOregon_Institute_of_Technology%2FOIT%253A_CHE_202_-_General_Chemistry_II%2FUnit_8%253A_Solutions_and_Phase_Changes%2F8.2%253A_Solubility_and_Intermolecular_Forces, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), 8.1: Heating Curves and Phase Changes (Problems), 8.2: Solubility and Intermolecular Forces (Problems), http://cnx.org/contents/85abf193-2bda7ac8df6@9.110, status page at https://status.libretexts.org, Describe the effects of temperature and pressure on solubility, State Henrys law and use it in calculations involving the solubility of a gas in a liquid, Explain the degrees of solubility possible for liquid-liquid solutions, Adelaide Clark, Oregon Institute of Technology, Crash Course Chemistry: Crash Course is a division of. Van der Waals ForcesKeesom Interactions. These interactions occur between permanent dipoles, which can be either molecular ions, dipoles (polar molecules) or quadrupoles (e.g. Debye Force. These interactions occur between permanent dipoles and induced dipoles. London Dispersion Force. Examples of Intermolecular Forces. Two liquids that do not mix to an appreciable extent are called immiscible. When these preventive measures are unsuccessful, divers with DCS are often provided hyperbaric oxygen therapy in pressurized vessels called decompression (or recompression) chambers (Figure \(\PageIndex{4}\)). The transport of molecules across the membrane of a cell or organelle can therefore be accomplished in a controlled and specific manner by special transmembrane transport proteins, a fascinating topic that you will learn more about if you take a class in biochemistry. (credit a: modification of work by Liz West; credit b: modification of work by U.S. Ikumi Aratani a, Yoji Horii * a, Daisuke Takajo b, Yoshinori Kotani c, Hitoshi Osawa c and Takashi Kajiwara a a Graduate School of Humanity and Science, Nara Women's University, Kitauoya-Higashimachi, Nara, 630 Fatty acids are derived from animal and vegetable fats and oils. CH3NH2 CH4 SF4 ONH3 BrF3. Hence, the two kinds of molecules mix easily. The acid ionization constant (Ka) of ethanol is about 10~18, slightly less than that of water. When a solutes concentration is equal to its solubility, the solution is said to be saturated with that solute. In addition, there is an increase in the disorder of the system, an increase in entropy. Everyone has learned that there are three states of matter - solids, liquids, and gases. Thus, the water molecule exhibits two types of intermolecular forces of attraction. How do you determine the strength of intermolecular forces?Boiling points are a measure of intermolecular forces.The intermolecular forces increase with increasing polarization of bonds.The strength of intermolecular forces (and therefore impact on boiling points) is ionic > hydrogen bonding > dipole dipole > dispersion. Because it is a very non-polar molecule, with only carbon-carbon and carbon-hydrogen bonds. Figure \(\PageIndex{1}\): The solubilities of these gases in water decrease as the temperature increases. Gases can form supersaturated solutions. The water at the bottom of Lake Nyos is saturated with carbon dioxide by volcanic activity beneath the lake. A similar set of resonance structures for the phenolate anion conjugate base appears below the phenol structures. 1-Pentanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is believed that the lake underwent a turnover due to gradual heating from below the lake, and the warmer, less-dense water saturated with carbon dioxide reached the surface. One of the lone pairs on the oxygen atom overlaps with the delocalised electrons on the benzene ring. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. WebWhich intermolecular force (s) do mixtures of pentane and hexane experience? Paul Flowers (University of North Carolina - Pembroke),Klaus Theopold (University of Delaware) andRichard Langley (Stephen F. Austin State University) with contributing authors. WebConstruction of a two-dimensional metalorganic framework with perpendicular magnetic anisotropy composed of single-molecule magnets. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Biphenyl does not dissolve at all in water. WebWhat is the strongest intermolecular force in Pentanol? Web9) Which of the following alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent? Hydrogen bonding: this is a special class of dipole-dipole interaction (the strongest) and occurs when a hydrogen atom is bonded to a very electronegative atom: O, N, or F. This is the strongest non-ionic intermolecular force. Here is another easy experiment that can be done (with proper supervision) in an organic laboratory. Notice that the entire molecule is built on a backbone of glycerol, a simple 3-carbon molecule with three alcohol groups. Evaporation requires the Have feedback to give about this text? << /Length 5 0 R /Filter /FlateDecode >> type of intermolecular forces (IMFs) exhibited by compounds can be used to predict whether two different compounds can be mixed to form a homogeneous solution (soluble or miscible). Thus, 1-pentanol is considered to be a fatty alcohol lipid molecule. These are hydrogen bonds and London dispersion force. The only strong attractions in such a mixture are between the water molecules, so they effectively squeeze out the molecules of the nonpolar liquid. 1-Pentanol is an organic compound with the formula C5H12O. WebThis is due to the hydrogen-bonding in water, a much stronger intermolecular attraction than the London force. ion-induced dipole D. dipole-dipole Part 2 (1 point) pentanol with another molecule of pentanol Choose one or more: WebWater and alcohols have similar properties because water molecules contain hydroxyl groups that can form hydrogen bonds with other water molecules and with alcohol If you are taking a lab component of your organic chemistry course, you will probably do at least one experiment in which you will use this phenomenon to separate an organic acid like benzoic acid from a hydrocarbon compound like biphenyl. When the beverage container is opened, a familiar hiss is heard as the carbon dioxide gas pressure is released, and some of the dissolved carbon dioxide is typically seen leaving solution in the form of small bubbles (Figure \(\PageIndex{3}\)). As noted in our earlier treatment of electrophilic aromatic substitution reactions, an oxygen substituent enhances the reactivity of the ring and favors electrophile attack at ortho and para sites. These intermolecular forces allow molecules to pack together in the solid and liquid states. Why is phenol a much stronger acid than cyclohexanol? Solubilities for gaseous solutes decrease with increasing temperature, while those for most, but not all, solid solutes increase with temperature. The difference, of course, is that the larger alcohols have larger nonpolar, hydrophobic regions in addition to their hydrophilic hydroxyl group. (credit: Yortw/Flickr). 1-Pentanol is an organic compound with the formula C5H12O. WebWhat intermolecular forces are present in pentanol and water The type of intermolecular forces (IMFs) exhibited by compounds can be used to predict whether two different compounds can be mixed to form a homogeneous solution (soluble or miscible). With this said, solvent effects are secondary to the sterics and electrostatics of the reactants. Figure \(\PageIndex{10}\): This hand warmer produces heat when the sodium acetate in a supersaturated solution precipitates. WebScience Chemistry Here's the Lewis structures for propane and water: HHH TTI H-C-C-C-H H H What intermolecular forces (IMFS) would be present between a propane molecule and a water molecule? { "13.04:_Preparation_of_Alcohols_via_Reduction" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.05:_Preparation_of_Diols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.09:_Reactions_of_Alcohols:_Substitution_and_Elimination" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.10:_Reactions_of_Alcohols:_Oxidation" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.11:_Biological_Redox_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.12:_Oxidation_of_Phenol" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.13:_Synthesis_Strategies" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.1:_Physical_Properties_of_Alcohols;_Hydrogen_Bonding" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.2:_Acidity_of_Alcohols_and_Phenols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.3:_Synthesis_of_Alcohols_-_Review" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.4:_Dehydration_Reactions_of_Alcohols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.5:_Oxidation_Reactions_of_Alcohols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.6:_Alcohols_from_Reaction_of_Carbonyl_Compounds:_Grignard_Reagents" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.7_Reactions_of_Alcohols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.8:_Protection_of_Alcohols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.9_Alcohols_from_Carbonyl_Compounds:_Reduction" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13.E:_Alcohols_and_Phenols_(Exercises)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "10:_Alkynes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "11:_Radical_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "12:_Synthesis" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "13:_Alcohols_and_Phenols" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "14:_Ethers_and_Epoxides;_Thiols_and_Sulfides" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "16:_Nuclear_Magnetic_Resonance_Spectroscopy" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "17:_Conjugated_Pi_Systems_and_Pericyclic_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "18:_Aromatic_Compounds" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "19:_Aromatic_Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1:_A_Review_of_General_Chemistry_-_Electrons,_Bonds,_and_Molecular_Properties" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "20:_Aldehydes_and_Ketones" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "21:_Carboxylic_Acids_and_Their_Derivatives" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "22:_Alpha_Carbon_Chemistry:_Enols_and_Enolates" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "23:_Amines" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "24:_Carbohydrates" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25:_Amino_Acids,_Peptides,_and_Proteins" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "26:_Lipids" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "27:_Synthetic_Polymers" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2:_Molecular_Representations" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "3:_Acids_and_Bases" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "4:_Alkanes_and_Cycloalkanes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "5:_Stereoisomerism" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "6:_Chemical_Reactivity_and_Mechanisms" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "6:_Infrared_Spectroscopy_and_Mass_Spectrometry_(Chapter_15)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7:_Substitution_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "8:_Alkenes:_Structure_and_Preparation_via_Elimination_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "9:_Addition_Reactions_of_Alkenes" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, 13.1: Physical Properties of Alcohols; Hydrogen Bonding, [ "article:topic", "showtoc:no", "license:ccbyncsa", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FWinona_State_University%2FKlein_and_Straumanis_Guided%2F13%253A_Alcohols_and_Phenols%2F13.1%253A_Physical_Properties_of_Alcohols%253B_Hydrogen_Bonding, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), 13.9: Reactions of Alcohols - Substitution and Elimination, Chemical Reactions of Alcohols involving the O-H bond of Compounds with Basic Properties, status page at https://status.libretexts.org, John D. Robert and Marjorie C. Caserio (1977).
Erik Lake Atlanta Pilot, Andrewsky Tiktok Lawyer, Articles P