There are many diverse tasks including: The NucleoCounter NC-3000 is an advanced image cytometer utilizing fluorescence, The assembly of linear polypeptide chains into functional three-dimensional protein architectures involves a unique force called hydrogen bonding. Almost every substance that people consume is excreted as parent compound and as metabolites via urine and. PH3 exhibits a trigonal pyramidal molecular geometry like that of ammonia, but unlike NH3 it cannot hydrogen bond. 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. The addition of other substances to water can dramatically alter these interactions and hence the properties of water. It can be suggested that hydrogen-bonding donors as well as acceptors in alcohol beverages, which exist as the initial components or are gained later on, should cause the tight association between . Chemical bonds are a form of negative energy, as you can see. The molecule breaks apart when the energy level drops to zero. The secondary structure of a protein involves interactions (mainly hydrogen bonds) between neighboring polypeptide backbones which contain nitrogen-hydrogen bonded pairs and oxygen atoms. Alcohols are substantially less volatile, have higher melting points, and greater water solubility than the corresponding hydrocarbons (see Table 15-1), although the differences become progressively smaller as molecular weight increases. Since opposite charges attract, these partial charges will line up in solution where the partially negative oxygen atom on one molecule will interact with the partially positive hydrogen atom of the other molecule. In this work we have utilised NMR relaxation time analysis, terahertz time-domain spectroscopy and neutron diffraction. The solubility of isomeric alcohols increases with branching because the surface area of the hydrocarbon part decreases with branching. Intake of alcohol can create harm to the tissues in the digestive tract. Calculations were performed at theab initio 3-21G and 6-31G** level, with and without correlation energy inclusion, using the Mller-Plesset approach Now, any atom with high electron density can get attracted to this partially positive H-atom. Whats that about? Comparison of the physical properties of alcohols with those of hydrocarbons of comparable molecular weight shows several striking differences, especially for those with just a few carbons. The combination of these aspects results in an easy penetration of ethanol through the bilayer. Despite the high energy content by mass, hydrogen has low density, and it is necessary to develop an, The phases of matter are characterized by the symmetries inherent to each state. The saturated carbon chain forms the alkyl group and is often designated by the symbol R. Hence, alcohols are commonly represented as shown below. The energy is less negative if you add it. This results in a hydrogen bond. Hydrogen bonding occurs between molecules in which a hydrogen atom is attached to a strongly electronegative element: fluorine, oxygen or nitrogen. The trinitro compound shown at the lower right is a very strong acid called picric acid. In order to be miscible, the original hydrogen bonds present in ethanol and water must be broken to form new hydrogen bonds between water and ethanol molecules. Alcohol. Lone pairs at the 2-level have electrons contained in a relatively small volume of space, resulting in a high negative charge density. This means that when theres a lot of salt, all of the water molecules will bond with the salt ions, leaving no hydrogen bonds with the alcohol molecules. The difference occurs by replacing a methyl group \(\left( {{\rm{ C}}{{\rm{H}}_{\rm{3}}}} \right)\) with hydroxyl \(\left( {{\rm{ OH}}} \right){\rm{. Point out that the bonding of the oxygen and hydrogen in the sucrose makes parts of the sucrose molecule polar in a similar way as in a water molecule. This means that oxygen will develop a slight negative charge \(\left( {{\rm{\delta }}} \right)\) and will become more electron rich (morenegative) than the hydrogen atom. Why does alcohol lower the boiling point of water? the bonds are called hydrogen bonds, and are responsible for the relatively high boiling points of alcohols. Extensiveness. Due to this the X-H bond behaves as a permanent dipole, with H as the positive pole. Clearly then, the reason alcohols have higher boiling points than corresponding alkyl halides, ethers, or hydrocarbons is because, for the molecules to vaporize, additional energy is required to break the hydrogen bonds. The same effect that is seen on boiling point as a result of hydrogen bonding can also be observed in the viscosity of certain substances. The hydrogen bonding between alcohol molecules is caused by the hydroxyl groups in alcohol molecules. Spatial probability densities of 2-propanol (methyl group green; oxygen red) and water (blue) at 90 mol % H2O. We have demonstrated that there are four to five water molecules in the immediate vicinity of an alcohol molecule using the advanced techniques described above. Why does soap weaken hydrogen bonds? The impact of adding alcohols to water is particularly interesting. The -OH ends of the alcohol molecules can form new hydrogen bonds with water molecules, but the hydrocarbon "tail" does not form hydrogen bonds. Hydrocarbons cannot dissolve in water. Alcohol Disrupts Hydrogen Bonding: Hydrogen bonding occurs between amide groups in the secondary protein structure. This situation becomes more pronounced with the increasing carbon chain. In a group of ammonia molecules, there are not enough lone pairs to go around to satisfy all the hydrogens. Soap is a component of fatty acid and glycerine.They are hydrophobic, which means they fear water. What are the types of hydrogen bonding? An alcohol is an organic molecule containing an -O-H group. The hydrogen bonds that hold the water molecules together at the surface are weakened as a result of this. If you plot the boiling points of the compounds of the group 14 elements with hydrogen, you find that the boiling points increase as you go down the group. Water frequently attaches to positive ions by co-ordinate (dative covalent) bonds. 13.1: Physical Properties of Alcohols; Hydrogen Bonding is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts. When two water molecules come close together, hydrogen bonds are easily formed, but when the water molecules move apart again, they are easily broken. Hydrogen bonds also occur when hydrogen is bonded to fluorine, but the HF group does not appear in other molecules. The hydrogen atom is then left with a partial positive charge, creating a dipole-dipole attraction between the hydrogen atom bonded to the donor and the lone electron pair of the acceptor. Supporting evidence that the phenolate negative charge is delocalized on the ortho and para carbons of the benzene ring comes from the influence of electron-withdrawing substituents at those sites. The general formula for the homologous alcohol series is \({{\rm{C}}_{\rm{n}}}{{\rm{H}}_{{\rm{2n + 1}}}}{\rm{OH}}\) where \({\rm{n}} = {\rm{ }}1,{\rm{ }}2,{\rm{ }}3,\) etc. In a weakly hydrogen-bond accepting environment, as mimicked here by acetonitrile, such an intramolecular hydrogen bond is likely formed, leading to a strong increase of the relative abundance of . These are the reason that upon turning to solid ice, water takes up more space that it does as a liquid. Between its molecules, the 1-butanol has the most attraction. However, when the molecules are mixed, new hydrogen bonds are formed between water molecules and ethanol molecules. Why is phenol a much stronger acid than cyclohexanol? The most stable arrangement is the . In order to mix the two, the hydrogen bonds between water molecules and the hydrogen bonds between ethanol molecules must be broken. To answer this question we must evaluate the manner in which an oxygen substituent interacts with the benzene ring. Chemical bonds are defined by the attractive forces between their nuclei and electrons, and can vary in range from only passing attraction to irreversible binding. For example, intermolecular hydrogen bonds can occur between NH3 molecules alone, between H2O molecules alone, or between NH3 and H2O molecules. In order for a hydrogen bond to occur there must be both a hydrogen donor and an acceptor present. Chang, Raymond. Is it possible for alcohol to break hydrogen bonds? In methoxymethane, the lone pairs on the oxygen are still there, but the hydrogens are not sufficiently + for hydrogen bonds to form. Consider two water molecules coming close together. This is why the boiling point of water is higher than that of ammonia or hydrogen fluoride. The cohesion-adhesion theory of transport in vascular plants uses hydrogen bonding to explain many key components of water movement through the plant's xylem and other vessels. The hydroxyl group (-OH) of an alcohol is special in that it acts. However, the hydrogen bonding between alcohol molecules are weaker than that in water because the other end of the alcohol molecule has a C-O bond which is less polar than the O-H bond. DNA replication:DNA copied into DNA Uncoiling the helix, strand separation by breaking hydrogen bonds between complementary strands, and two new strand synthesis by complementary base pairing are all examples of DNA replication. Hydrogen bonding is not the only intermolecular force present in alcohols. The hydrogen bonding in the ethanol has lifted its boiling point about 100C. Hydrogen bonding is type of intermolecular force, meaning it describes how certain molecules are attracted to each other. This would also significantly reduce the amount of heat required for phase changes from ice to liquid and liquid to vapor. The flexible skin stretches into a sphere shape (round like a ball) when the air gets trapped beneath the surface of the soap and water mixture, creating a bubble! Soap or alcohol affects the hydrogen bonds between different water molecules due to their hydrophobic nature.They lower the hydrogen bonding between water by pushing their atoms up.. What are soap and alcohol? The boiling points of ethanol and methoxymethane show the dramatic effect that the hydrogen bonding has on the stickiness of the ethanol molecules: The hydrogen bonding in the ethanol has lifted its boiling point about 100C. These relatively powerful intermolecular forces are described as hydrogen bonds. Chemistry:The Central Science. These interactions between the negative oxygen atom and positive hydrogen atom result in the formation of hydrogen bonds. . Some of the physical properties of alcohols are: The lower alcohols are colourless liquids with a characteristic smell and a burning taste. Cancer | Breast cancer | Tumor An important principle of resonance is that charge separation diminishes the importance of canonical contributors to the resonance hybrid and reduces the overall stabilization. I can tell you, as, A flashing blue light and a flashing lockout reset button are usually signs that the ignition is locked. This overlap leads to a delocalization which extends from the ring out over the oxygen atom. Hydrogen bonding cannot occur without significant electronegativity differences between hydrogen and the atom it is bonded to. The chart below shows the boiling points of some simple primary alcohols with up to \(4\) carbon atoms compared with those of the equivalent alkanes (methane to butane): \(\mathop {{\rm{C}}{{\rm{H}}_3}{\rm{OH}}}\limits_{{\rm{Methanol}}} \quad \mathop {{\rm{C}}{{\rm{H}}_3}{\rm{C}}{{\rm{H}}_2}{\rm{OH}}}\limits_{{\rm{Ethanol}}} \quad \mathop {{\rm{C}}{{\rm{H}}_3}{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_2}{\rm{OH}}}\limits_{{\rm{Propan 1 ol}}} \quad \mathop {{\rm{C}}{{\rm{H}}_3}{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_2}{\rm{Ol}}}\limits_{{\rm{Butan 1 ol}}} \). We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Alcohols have significantly higher boiling points than alkanes. Solubility : Primary < Secondary < Tertiary. Phenol can lose a hydrogen ion because the phenoxide ion formed is stabilised to some extent. When it comes to the paper ball, this lower surface tension has two direct effects. (see Interactions Between Molecules With Permanent Dipoles). ( Watch on YouTube : Alcohol Properties. Ethanol is able to form hydrogen bonds with the lipids in the bilayer (see Hydrogen Bonding of Alcohol to Lipids, below), and these hydrogen bonds reduce the order parameter of the lipid hydrocarbon chains. This phase transition is accompanied by the crystallization of H2O molecules,, The coexistence between excessive alcohol consumption and hepatitis C virus (HCV) infection is causative of a high death ratio annually. The presence of hydrogen bonds also makes water molecules more 'sticky' or in scientific terms cohesive and adhesive. As the molecules grow longer and have more electrons, the attraction between them becomes stronger. In the case of ammonia, the amount of hydrogen bonding is limited by the fact that each nitrogen only has one lone pair. Many elements form compounds with hydrogen. Brown, et al. The two strands of the famous double helix in DNA are held together by hydrogen bonds between hydrogen atoms attached to nitrogen on one strand, and lone pairs on another nitrogen or an oxygen on the other one. . Blood pressure | Heart The hydrogen bonding is limited by the fact that there is only one hydrogen in each ethanol molecule with sufficient + charge. So, 'O' atom attract O -H bonded electrons towards itself . Without hydrogen bonds, water molecules move faster and more quickly with less heat energy input, increasing the temperature for each calorie of added heat. This phenolic acidity is further enhanced by electron-withdrawing substituents ortho and para to the hydroxyl group, as displayed in the following diagram. Fig. The energy released when these new hydrogen bonds form approximately compensates for the energy needed to break the original interactions. This is due to the tiny, weak hydrogen bonds that hold water molecules together for fractions of a second in billions of seconds. All of these are disrupted by the addition of another alcohol. . Water is an ideal example of hydrogen bonding. The \({\rm{ OH}}\) end of the alcohol molecule forms new hydrogen bonds with water molecules, but the hydrocarbon tail does not form hydrogen bonds. Ethanol is able to form hydrogen bonds with the lipids in the bilayer (see Hydrogen Bonding of Alcohol to Lipids, below), and these hydrogen bonds reduce the order parameter of the lipid hydrocarbon chains. Just as they do in water, the hydroxyl groups in alcohols form hydrogen bonds with one another-that is, they form loose bonds between the hydrogen atom of one hydroxyl group and the oxygen atom of . In order for this to happen, both a hydrogen donor a hydrogen acceptor must be present within one molecule, and they must be within close proximity of each other in the molecule. In the cases of \(NH_3\), \(H_2O\) and \(HF\) there must be some additional intermolecular forces of attraction, requiring significantly more heat energy to break the IMFs. The size of the transient dipoles created grows as a result of this. However, solubility decreases as the length of the hydrocarbon chain in the alcohol increases. }}\), Replacing both the \({\rm{ C}}{{\rm{H}}_{\rm{3}}}\) groups on propane with an \({\rm{OH}}\) group gives us ethylene glycol, a di-ol also called a vicinal diol would be more polar than Propanol and thus have a higher boiling point. Explain that sucrose has polar areas caused by the same type of oxygen-hydrogen covalent bonds as in the water molecule. The knowledge of the meso-scale structure of such mixtures directly informs the design of such processes and products. Oxygen has an electronegativity of \(3.5,\) whereas the electronegativity of hydrogen is \(2.2.\) Oxygen, being more electronegative than hydrogen, will pull the shared pair of electrons towards itself. The classical hydrogen bond. Other examples include ordinary dipole-dipole interactions and dispersion forces. The \({\rm{ - OH}}\) end of the alcohol molecule forms new hydrogen bonds with water molecules, but the hydrocarbon "tail" does not form hydrogen bonds. Until now, however, experimental data on the molecular properties that emerge from such solutions came primarily from neutron diffraction analysis and sent mixed messages. Be sure to count the drops! Structure and dynamics of aqueous 2-propanol: a THz-TDS, NMR and neutron diffraction study. Using a clean pipette, add water to the penny drop by drop until it overflows. The presence of hydrogen bonding in alcohols imparts a much greater solubility of alcohols in water. These bonds are about \(1/10\) as strong as normal bonds. { "Dipole-Dipole_Interactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Dipole_Moment : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Dipole_moments : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Hydrogen_Bonding : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", "Ion_-_Dipole_Interactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", "Ion_-_Induced_Dipole_Interactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", "Ion_-_Ion_Interactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", "Lennard-Jones_Potential" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", London_Dispersion_Interactions : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Polarizability : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Van_Der_Waals_Interactions : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()" }, { Hydrogen_Bonding : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Hydrophobic_Interactions : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Multipole_Expansion : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Overview_of_Intermolecular_Forces : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Specific_Interactions : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()", Van_der_Waals_Forces : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass226_0.b__1]()" }, [ "article:topic", "hydrogen bonding", "showtoc:no", "license:ccbyncsa", "licenseversion:40", "author@Jim Clark", "author@Jose Pietri" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FPhysical_and_Theoretical_Chemistry_Textbook_Maps%2FSupplemental_Modules_(Physical_and_Theoretical_Chemistry)%2FPhysical_Properties_of_Matter%2FAtomic_and_Molecular_Properties%2FIntermolecular_Forces%2FSpecific_Interactions%2FHydrogen_Bonding, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), More complex examples of hydrogen bonding, Hydrogen bonding in organic molecules containing nitrogen, status page at https://status.libretexts.org, methoxymethane (without hydrogen bonding). Alcohols are often referred to as polar protic solvents. Hydrogen bonding in alcohols An alcohol is an organic molecule containing an -OH group. Rubbing alcohol molecules have polar and nonpolar parts, which means they can form hydrogen bonds with water and mix with it as a result. [1] When two or more hydroxyl groups are present in an organic molecule, hydrogen bonding increases and the boiling point rises sharply. VARIABLE: ISOPROPYL ALCOHOL Alcohol and Water Alcohol has one O-H bond which is polar but a large portion of the molecule is made up of C-H We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Hence , the bond becomes more polar which is eligible for the formation of inter molecular hydrogen bond . DNA | RNA | Receptor | Nanoparticles Depending on the drop size, about 20 to 30 drops of ethyl alcohol can be sprinkled on a coin. It is caused by the attractive force between a hydrogen atom that is covalently bonded to an electronegative atom, such as a N, O, or F atom, and another electronegative atom. Water is thus considered an ideal hydrogen bonded system. open and H-centred conformations, were optimized and the hydrogen bond energies evaluated, in order to estimate the effect of 3-substitution steric hindrance on the hydrogen bond strength. Heat, on the other hand, weakens chemical bonds by making molecules more difficult to dissociate. Click cc for transcription.) Spreading the charge around makes the ion more stable than it would be if all the charge remained on the oxygen. . Although the lone pairs in the chloride ion are at the 3-level and would not normally be active enough to form hydrogen bonds, they are made more attractive by the full negative charge on the chlorine in this case. A salt bond is a weak, cross-linking side bond that can be broken by pH changes. The molecules are bonded together by hydrogen bonds, which form a dense structure. Fig. Flammability. This means the primary alcohols have higher boiling points than the secondary alcohol (\(2-\)butanol) which has a higher boiling point than the tertiary alcohol (\({\rm{t }}\)butanol). Necessary . An alcohol contains a polar -OH group in its molecules. Larger molecules have more space for electron distribution and thus more possibilities for an instantaneous dipole moment. This accounts for the higher boiling points in alcohols. 3. The acid ionization constant (Ka) of ethanol is about 10~18, slightly less than that of water. The presence of hydrogen bonding in alcohols accounts for the higher boiling points of alcohols than their analogous alkanes. The diagram shows the potential hydrogen bonds formed with a chloride ion, Cl-. Formulas illustrating this electron delocalization will be displayed when the "Resonance Structures" button beneath the previous diagram is clicked. It neither produces \({{\rm{H}}^{\rm{ + }}}\) nor \({\rm{O}}{{\rm{H}}^{\rm{ }}}\) ions in the solution. The extent of hydrogen bonding decreases with increase in temperature and pressure, and with addition of electrolytes into the solution, which leads to a reduction of the "solvent quality" of water. This kind of drink is capable of reducing the contact between the brain and the body. 1. They do this by polarization of their bonding electrons, and the bigger the group, the more polarizable it is. For example, this directly impacts on the mobility of hydrogen through the liquid media a key step in many chemical processes including hydrogenation reactions; the viscosity of the mixture; and other related properties such as the velocity of sound through the mixture. The alcohol molecules are therefore intimately mixed throughout the water, altering its hydrogen bonding structure and hence its properties. They are used to washing clothes and bodies. Note A base is a chemical that takes hydrogen ions while an acid donates hydrogen ions. Instead of a covalent bond to a hydrogen atom, hydrogen bonding is a special type of dipole-dipole attraction between molecules. A similar set of resonance structures for the phenolate anion conjugate base appears below the phenol structures. An alcohol is an organic molecule containing an -O-H group. 2-propanol, has the potential to have a significant impact in any area where water finds application: from catalysis, to fuel cells, to biological processing to alcoholic beverages. 11th ed. 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. 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