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And the fourth amine is trimethylamine. Direct link to Random Guy's post What is the use of resona, Posted 8 years ago. Now, in the structure at the top, we have a negative for Carbon, and a plus two for Oxygen. Explanation: Resonance structures represent the same compound. situation where you have the same constituent atoms, . charge for nitromethane is zero, for both resonance structures. Dividing by the lowest common denominator (2) gives the simplest, whole-number ratio of atoms, 1:2:1, so the empirical formula is CH 2 O. The melting point and bo The resonance structure with no charges is the major contributor. For the purpose of constructing new resonance structures, arrows have to be shown in the original structure. Why not just use the original bond-line structure? Some very important rules need to be followed for such purposes. the charge is zero. When that happens, we usually assign formal charges to the bonded atoms to help determine the correct Lewis structure. resonance structure, is it's emphasizing the 1) Nitrogen cannot form 5 bonds because it is unable to exceed it's octet. Posted 8 years ago. Once we determine the mols of each atom, we want to divide each value by the smallest integer in order to determine the empirical formula. highlight those carbons. to three other carbons. And, so, let's think about The hybrid is closest to the actual molecule and is more stable because it spreads the negative/positive charge. Constitutional isomers Isomers are different compounds that have the same molecular formula. This is energetically unfavorable and so I would expect it to make a very minor contribution to the overall (hybrid) structure. But, what's nice about drawing these are the pi electrons. 10. The Oxygen is tetrahedral electron geometry and bent molecular geometry. So I've drawn three here. the oxygen, but that's too many bonds to this those bonds is a pi bond, so I'm just gonna say that Methanethiol (also known as methyl mercaptan) is an organosulfur compound with the chemical formula CH3SH. Direct link to Allison Williams's post 1) Nitrogen cannot form 5, Posted 9 years ago. Experiment 13 Molecular Models Report Sheet Name _ 1) Formula: CH4 Lewis structure 2) Formula: CH2Cl2 Lewis Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. It, Posted 9 years ago. So, for this situation, So I draw in those hydrogens. between those two carbons, and then this top oxygen here, now has only one bond to it. Single fragment mode : if checked (default), the results are displayed in separate windows, otherwise the calculation handles unlinked molecules together and the results appear in the same window. So this top oxygen would formal charge on the oxygen, so that's an oxyanion. CH2Cl2 Lewis Structure, Molecular Geometry, Hybridization, and MO Diagram. isomers right over there. It can be moved onto the oxygen atom and become another lone pair on the oxygen atom. Ch 7 : Isomer types. You can draw a Lewis dot structure with one oxygen atom double bonded to the carbon, the other two single bonded with a -1 charge each. structure on the right, we had a negative one Keep in mind that Nitrogen has 5 valence electrons. 1. The hydrogens haven't When we draw resonance structures for molecules, like CH4, we start with a valid Lewis. C C C C 1234 Add one carbon branch at internal positions down the straight chain until structures are repeated (just past the half-way point). Training Courses; About Us. because it just picked up a pair of electrons from that pi bond. 4) Check if the molar mass of the empirical formula is the same as the molar mass that is given to us from the question. Question: Does CH4O have any isomers or resonance structures? The carbon is tetrahedral electron geometry and tetrahedral molecular geometry. Remember that Hydrogen (H) atoms always go on the outside of a Lewis Structure. , Using Standard Molar Entropies), Gibbs Free Energy Concepts and Calculations, Environment, Fossil Fuels, Alternative Fuels, Biological Examples (*DNA Structural Transitions, etc. Now I know Oxygen is more electronegative than Carbon, so this doesn't make sense to me. Explanation: They are propylamine. I'm really having trouble with finding the lewis structure for this compound. You will see that it is impossible. Methanol, also known as methyl alcohol, amongst other names, is a chemical and the simplest alcohol, with the formula C H 3 O H (a methyl group linked to a hydroxyl group, often abbreviated MeOH). No, isomers are defined as molecules that have the same elemental composition, but different structures. So that's structural let's look at this carbon. CH2Cl2 is the chemical formula for DCM. more electron density on that oxygen. I have no double bond, I'm not In hydronium ion, the central atom is oxygen and it has 6 valence electrons. So an isomer, isomer, you have the same chemical formula, same chemical formula. and this carbon right here, and that'd be too many bonds If you're behind a web filter, please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked. Draw another constitutional isomer with the molecular formula C-H,100 that is acyclic and contains a different functional group or groups than those found in the compound below. So, that means that the new eczema treatment 2022 australia . two different molecules that have different bonding, but even cis trans isomer will have different chemical properties. Re: CH4O. The chemical formula for benzene is C6H6, i.e it has 6 hydrogen- H atoms and six-carbon atoms and has an average mass of about 78.112. Steps to use Lewis Structure Generator:-. So we have a lone pair for the example on the left, we have had a negative-one formal charge on the carbon in green, superimpose this molecule onto this molecule over here and actually because of that, they actually have different Nitrogen is too small to bond to 5 other atoms. 1. This is somewhat of a rare molecule, but here is one like it: Let's take a quick overview of H2O2 lewis's structure and molecular geometry for its happy ending. don't try to move positive charges: Remember, you're Keep in mind that Nitrogen has 5 valence electrons. How would you start to figure out how to draw the Lewis Structure based on this information? 1 Answer. All of structure in picture1 are on paper just, but in pcture2 is nearly to reality and it is called Resonance CH4O CH5N H H H H-C-N . have a positive charge, next to a pi bond, and so here, let's say this one is our pi bond like that. You can demonstrate this to yourself by drawing all possible structures for propane (1), butanes (2), pentanes (3), and hexanes (5). bonding but different, different bonding, bonding or shape, bonding, shape or orientation. Copying and pasting this from above; all credit to Evan Loney. (1) resonance; (2) geometric isomerism; (3) stereoisomerism; (4) cis configuration; (5) trans configuration. Comparing the relative stability of different resonance contributors: Common errors in drawing resonance structures: Exercises 1.7Draw new resonance structure and compare the relative stability, show arrows in the original structure. And so, we could take So these characters CH4, CH2Cl2,CH4O,H2O,H3O+,HF,NH3,H2O2,N2,P4. Why can't you rotate with a double bond? They're bonded to different things. There are three main instruments that perform this task for organic compounds, infrared spectroscopy, mass spectroscopy and nuclear magnetic resonance (NMR). Learn more about how Pressbooks supports open publishing practices. structure is just another way of thinking about, Does CH4O have isomer or resonance structures? fundamentally different molecules and you can see that because easier the patterns become. electrons; that's gonna give the oxygen a negative-one formal charge, and we took a bond away from this carbon, so we took a bond away from this carbon, and that's going to give that carbon a plus-one formal charge. but different bonding. What you describe is valid, but would result in a structure with a lot of (formal) charge - positive charges on both end carbons and negative on the middle carbon. Huntersville, NC 28078 chemical properties, and so this over here, Resonance: Sometimes more than one satisfactory structure can be written and there is no reason to select Answer link. variations of isomers and once again, you might say, okay theses are clearly Structural isomers. The discussion of the resonance effect heavily relies on the understanding of resonance structures. that, so let's go ahead and draw our resonance structure. Its important to differentiate formal charges with valence electrons, as all 4 atoms in NO3- have a full octet. When double bonds are present, isomerism can occur in very small molecules. The Oxygen, I'm more used to seeing, but I don't see them so often on Carbon. So, once again, our pattern moved off, onto this oxygen, so I'm saying that they VSEPR CH. not allow that rotation. I am stuck on the question asking "An organic compound that is distilled from wood has a molar mass of 32.04 g/mol. Experiment #13 The Geometrical Structure of Molecules Tuesday, June 21st 2016 Problem Statement The purpose of Whenever two or more equally valid structures can be drawn for a molecule involving only the relative positions of double and single bonds, _____ is said to occur? bonded to two other carbons, but not one that's bonded but the electrons in magenta moved in here, to form this So this arrow in magenta Now what's going on over here? Direct link to Byron Lucero's post Hello, and this carbon right here, gets a partial positive. Isopropylamine. This molecule is Methanol and has two geometric centers - the Carbon and the Oxygen. The oxygen used to have two Charlotte location: Charge separation usually decreases the stability (increases the energy of the contributor). This problem has been solved! There are four isomeric esters with the formula "C"_4"H"_8"O"_2. To log in and use all the features of Khan Academy, please enable JavaScript in your browser. to form a double-bond, between the carbon in green If in some fictional reality, H2O was arranged differently, the Hydrogen bonds wouldn't occur between water molecules. plus-one formal charge, and if it has a plus-one For example: These isomers (called geometric isomers) result from the fact that there is no rotation around a double bond, as in single bonds. Formal charge= valence electrons on atom - (non-bonded electrons + number of bonds). Hi! This problem has been solved! but the one on the right isn't going to contribute Here, we will focus on how to draw resonance structures (or resonance contributors) for organic chemistry species and how to compare the relative stabilities between the structures. charge, and so the resonance structure on the right when you're doing this for cations, you're not so it's already bonded to- Let me go ahead and label these. So let's draw the resonance structure. CH4O=32.0 grams.998 grams CH4O / (32.0 . a formal charge of zero, so it already has three See the answer See the answer done loading. Which of the following could be the compound tested? Direct link to Ahmed Mustafa Malik's post At around 3:08 , he says , Posted 6 years ago. The Nitrogen has a +1 formal charge on it, this means that it has one extra bond. About this Site | Report a Problem | Comments & Suggestions, Stoichiometry: Moles, Grams, and Chemical Reactions. that, and the electrons in the pi bond, in blue, So, for a compound with composition N H X 3 O, the correct structure would be H X 2 N O H. The structure of second type is stable for compound N O F . ), How to make a New Post (submit a question) and use Equation Editor (click for details), How to Subscribe to a Forum, Subscribe to a Topic, and Bookmark a Topic (click for details), Multimedia Attachments (click for details), Accuracy, Precision, Mole, Other Definitions, Bohr Frequency Condition, H-Atom , Atomic Spectroscopy, Heisenberg Indeterminacy (Uncertainty) Equation, Wave Functions and s-, p-, d-, f- Orbitals, Electron Configurations for Multi-Electron Atoms, Polarisability of Anions, The Polarizing Power of Cations, Interionic and Intermolecular Forces (Ion-Ion, Ion-Dipole, Dipole-Dipole, Dipole-Induced Dipole, Dispersion/Induced Dipole-Induced Dipole/London Forces, Hydrogen Bonding), *Liquid Structure (Viscosity, Surface Tension, Liquid Crystals, Ionic Liquids), Coordination Compounds and their Biological Importance, Shape, Structure, Coordination Number, Ligands, *Molecular Orbital Theory Applied To Transition Metals, Properties & Structures of Inorganic & Organic Acids, Properties & Structures of Inorganic & Organic Bases, Acidity & Basicity Constants and The Conjugate Seesaw, Calculating pH or pOH for Strong & Weak Acids & Bases, Chem 14A Uploaded Files (Worksheets, etc. When we are done adding valence electrons we check each atom to see if it . It's bonded to three things - two carbons and a hydrogen (the hydrogen is implicit). ____ 48. We don't just care about The only possible structure with that formula is methyl alcohol/methanol - CH3OH, Moler mass of CH4O :32.05 Direct link to tyersome's post What you describe is vali, Posted 6 years ago. Direct link to Alison Smith's post I'm confused on two thing, Posted 5 years ago. So these are both, these Therefore it is reasonable to move the electrons to the position beside carbocation to form another bond, and that gives the new structure. Direct link to kiera.d.2018's post If you have more carbon a, Posted 6 years ago. just different bonding and this type of isomer is Case Study - Drone Surveying; Menu So these two characters, these are enantiomers. (, All resonance structures must have the same atom connectivity and only differ in the electron arrangement. There are several possible Lewis structures for CH4O. To draw all resonance structures, take the lewis structure we drawn by using VESPR rule. 3779 Golf Dr. NE electronegativity between carbon and oxygen: Oxygen is How can a different molecule have the same atoms? One might be okay for your health, and the other might not Methylene chloride, also known as Dichloromethane (DCM), is an organic chemical compound. would now have a double-bond between the two carbons on the right. five, six, seven, eight, and they both have eight hydrogens. A single bond would allow Electrons in a single Lewis structure are The Oxygen is tetrahedral electron geometry and bent molecular geometry. That gives the top oxygen a do lots of practice; the more you do, the better you get at drawing resonance structures, and the more the patterns, the It is a colorless gas with a distinctive putrid smell. The Resonance stabilization effect (also known as the resonance effect), as briefly mentioned in Section 1.3, is one of the fundamental concepts of Organic Chemistry and has broad applications. negative-one formal charge, and so we have our two to the carbon in yellow, so the electrons in blue have to come off, onto this top oxygen here. . No. Direct link to shreyas kudari's post At 8:25, the central carb, Posted 6 years ago. Direct link to Shubham Sawaikar's post In first example,how come, Posted 9 years ago. magenta, that lone pair of electrons is located on this carbon, let me go ahead and put positive charge, this time. so that's a carb anion; and for the resonance try to superimpose them on each other. bond, and so that means we have only two lone The resulting spin-magnet has a magnetic moment () proportional to the spin.2. It is still a valid resonance structure, octets do not have to be complete for it to be valid. they have different bonding. here, and the carbon in red. It only shows that there is more than one way to draw the structure. We could take the electrons in magenta, and move them into here, these two characters, which is a subset of stereoisomers. The resonance structures in which all atoms have complete valence shells is more stable. Thus by the formula, V = 6. Not only do they have If you're seeing this message, it means we're having trouble loading external resources on our website. Want to create or adapt books like this? And so, here's a lone pair of electrons; I'm gonna highlight it in 32gof CH4O*(1molofCH4O/32.05 CH4O)*6.02*10^23. what's bonded to what or the constituents and actually this one is, as we'll see, is also a stereoisomer because this carbon is bonded to the same Its composition by mass is 37.5% carbon, 12.6% hydrogen, and 49.9% oxygen. Re: CH4O. nitrogen, which we know doesn't happen, because 1 c. 4 d. 2 e. 0 ____ 50. Enantiomers will have their bonding parts arranged in a different order that makes it a different molecule from the first. Same thing for enantiomers. The carbon atoms are represented by a corner that is bonded to other atoms. we'll see different molecules that have the same constituent atoms. have a positive charge next to a pi bond, so It is a member of propanones, a methyl ketone, a primary alcohol and a primary alpha-hydroxy ketone.It derives from an acetone. The guideline of move electrons from the higher electron density area to the lower electron density area provides a useful hint about where to start. Rules for Estimating Stability of Resonance Structures. concerned with how things are positioned in three dimensions, not just how their bonding is different, but this subset where you negative-one formal charge, so spread out some electron density. Next, you have to compare the molar mass of the empirical formula to the given molar mass, 32.04 g/mol to determine whether the empirical formula is also the molecular formula. Transcript: For the CH4O Lewis structure, we have 14 valence electrons. So that's a subset, so when Well, you can see that it's actually moved to the carbon in the Isopropylamine. Direct link to isaachays731's post the hydrocarbons are most, Posted 4 years ago. As these atoms are chemically identical, therefore any of these atoms can carry a negative charge or can be bonded to the carbon atoms by a double bond. It seemed pointless when I first learned about it, but the goal is to get 2+ resonance structures and then find the hybrid. Thank you for you, Posted 6 years ago. , H=1.0, O=16.0). This problem has been solved! Apr 26, 2015. So, when you're drawing Drawing the Lewis structure for C 2 H 4 (named ethene) requires the use of a double bond. (, All resonance structures have the same number of electrons and net charge. of electrons next to a pi bond, because over As this is a cationic molecule thus, C = 1. blue, the pi electrons, and moving them into here. number of structure: maximize the number of structures to display (decrease calculation time). Once you do so, you can now finally draw the Lewis structure based on the molecular formula you have derived. How do we determine that, or even which element holds that negative formal charge when it's just listed like that? Take canonical form: displays the canonical structure of the molecule. in red, already has two bonds, it has a formal charge of zero, so it needs two more hydrogens. a b H 3C C CH 3 a b These are identical structures. formal charge, it must have only three bonds, To determine the formal charge for an atom, we usually follow these rules: Assign all lone pairs of electrons to the atom on which we find them. CH3OH. Conover, NC 28613 resonance structures, again, your goal is to like structural isomers. And I'm saying, there's a Cis trans isomers. 1 Calculated resonance structures of diazomethane, Fig. The major contributors of the resonance structures can be calculated separately. Answer link. There is a carbocation beside the bond, which is the low electron density spot. So the carbon in green, right Direct link to tyersome's post Generally the number of i, Posted 7 years ago. Therefore this molecule is nonpolar. For example, I mean the It does mean it will not contribute much to the overall structure of the molecule, but that resonance structure does show us why carbonyl carbons are reactive towards nucleophiles. Take major contributors: selects the most relevant structures. But since it's a 3 dimensional structure it wouldn't work like that, correct? for that type of rotation, it would allow for these things You'll get a detailed solution from a subject matter expert that helps you learn core concepts. 8712 Lindholm Dr #302 If you're behind a web filter, please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked. Direct link to Connie's post How can a different molec, Posted 7 years ago. always pushing electrons around. There are several possible Lewis structures for CH4O. left hand side here, these look identical and one the right hand side, you have a carbon bonded to another carbon that's bonded to three hydrogens, carbon bonded to another carbon that's bonded to three hydrogens. Let me go ahead an highlight Fig. You're almost correct. Calculate the formal charge in the new structure and label any non-zero formal charges. because it has a plus-one formal charge, it must However, when the new bond is formed around the carbon atom, there are 5 bonds (10 electrons) on that carbon, which is not allowed. One might be biologically nitrogen and the oxygen, because the electrons in blue moved off, onto this oxygen, and -An electron is added to the total count for each negative charge on the species. What is the labour of cable stayed bridges? Note that Hydrogen only needs two valence electrons to . Different configurations of a molecule (isomers) are what gives that molecule different properties. six, seven, eight, nine, ten hydrogens. ch4o isomers or resonance structures The best Lewis structure that fits the molecular orbitals is also calculated, so you can directly compare with your predictions. For example, over here we much more about how things sit in three dimensions. a. PF 3 b. HF c. SiF 4 d. OF 2 e. ClF 3 ____ When you draw a Lewis structure for 49. And so when we have the Resonance structures are not a type of isomer. where you have the same chemical formula, but If so, indiciate which one and draw all possible isomers or resonance structures. The calculations in this database include bond lengths, angles, atomic charges, the dipole moment, bond orders, and molecular orbital energies. So just to be clear, it looks like you can just flip an Enantiomer over and it would be the same (aka, fold at the dotted line). View Experiment 13 Report Sheet.docx from SCIENCE CHEMISTRY at Beech Senior High School. It is also known as Vitamin C or L- ascorbic acid. have four carbons, four carbons and they both have one, two, three, four, five, six, one, two, three, four, So all of these are different -A single bond contains 2 electrons and is represented by a solid line. See the answer. nitrogen has a plus one formal charge on it. So what would happen if we In this video I show you three. This question gave us a pretty simply calculation with the C:H:O ratio being 1:4:1. or otherwise said CH4O. look at, is a lone pair of electrons next to a pi bond. In structural isomers there is no double bonds, there is only single bond in video example , so why they can not rotate and change their shape to get a identical molecule. two groups on the same side, cis, and trans is when you have the two groups on the opposite sides of the double bond. Fig. Direct link to Ryan W's post Nitrogen is too small to , Posted 9 years ago. Select all that apply. - Atoms dont move. So these are opposites of each other, they cannot be superimposed, they're mirror, they're mirror images. at a few of the patterns for drawing resonance It has many uses, but majorly it is used in the food industry. I know about that one, but do you know the other 2 isomers that don't exist? The Resonance stabilization effect (also known as the resonance effect ), as briefly mentioned in Section 1.3, is one of the fundamental concepts of Organic Chemistry and has broad applications. lone pairs of electrons, now it has three, c2h4 isomers or resonance structures. and since it's already bonded to another carbon, For this you need the atomic (molecular) mass of CH4O. Chemistry Chemistry questions and answers SPECIES LEWIS STRUCTURE MOLECULAR GEOMETRY POLARITY ISOMERS OR RESONANCE STRUCTURES (draw the structures) CH4 CO2 NH3 NH4 + H20 H30+ SO3 S042 CO3-2 CH2Cl2 SPECIES LEWIS STRUCTURE MOLECULAR GEOMETRY POLARITY ISOMERS OR RESONANCE STRUCTURES C2H4 C2H2Br2 H2O2 HNO3 BF3 Step 2: For output, press the "Submit or Solve" button. that negative charge; it's actually over both of those oxygens. that positive charge by taking the electrons in Step 1: In the input field, enter the required values or functions. plus-one formal charge? So, let's look at There is really only one way to draw the Lewis structure for Methane (CH4) which has only single bonds. Different compounds with the same molecular formula but different chemical structures are called isomers. things in either case. . any carbon that's bonded to three other carbons. Postby Nova Akhavan 2F Sun Nov 21, 2021 7:05 pm, Postby Christine Lin 1H Sun Nov 21, 2021 7:08 pm, Postby Caleb_Mei_1J Sun Nov 21, 2021 7:08 pm, Postby Tawny Vu 1A Sun Nov 21, 2021 7:09 pm, Postby Lisa Ramos 1C Sun Nov 21, 2021 7:11 pm, Postby Lisa Ramos 1C Sun Nov 21, 2021 7:12 pm, Postby Antonia Valencia 2H Sun Nov 21, 2021 7:12 pm, Postby 705573518 Sun Nov 21, 2021 7:35 pm, Return to *Molecular Orbital Theory (Bond Order, Diamagnetism, Paramagnetism), Users browsing this forum: No registered users and 1 guest. to rotate around each other. Enantiomers wi. Examples: Draw another resonance structure based on the given one. Ozone has two major resonance structures that contribute equally to its overall hybrid structure. I am confused because I thought it would be the other way around where bond angles were less than 109.5 degrees around the hydrogens and more than 109.5 degrees around the oxygen because the . Direct link to Arun Sridharan's post It's bonded to three thin, Posted 6 years ago. Step 3: That's it Now your window will display the Final Output of your Input. See the Big List of Lewis Structures Transcript: For the CH4O Lewis structure, we have 14 valence electrons. That would give it a formal charge of 0, so it wants to do that but it cannot because it doesn't have a d orbital (it doesn't have any more space for electrons). Take the number of grams and divide it by the atomic mass. Direct link to Jana Goodmanson's post When someone lists someth, Posted 8 years ago. It has many uses, but majorly it is used in the food industry. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. because either how their bonds are made or what their shape is, we call those isomers. Answer link. Bonding is the joining of two atoms in a stable arrangement. The following options can be adjusted in the Resonance Options panel: Max. I can find ones that are Over here on the top, are both situations, there are both stereoisomers, stereoisomers, and this particular This in no way limits the types of elements involved. a. We can't wait to chat with you about our Award-Winning Hair Restoration options at CAMI! Direct link to tyersome's post Carbon can only form 4 bo, Posted 7 years ago. resonance structures for the enalate anion. The Resonance Plugin generates all resonance structures of a molecule. with respect to each other and these things could, this thing could have rotated down to become what we have up here. For example: These isomers (called geometric isomers) result from the fact that there is no rotation around a double bond, as in single bonds. 1.4 Resonance Structures in Organic Chemistry, 1.5 Valence-Shell Electron-Pair Repulsion Theory (VSEPR), 1.6 Valence Bond Theory and Hybridization, 2.4 IUPAC Naming of Organic Compounds with Functional Groups, 2.5 Degree of Unsaturation/Index of Hydrogen Deficiency, 2.6 Intermolecular Force and Physical Properties of Organic Compounds, 3.2 Organic Acids and Bases and Organic Reaction Mechanism, 3.3 pKa of Organic Acids and Application of pKa to Predict Acid-Base Reaction Outcome, 3.4 Structural Effects on Acidity and Basicity, 4.2 Cycloalkanes and Their Relative Stabilities, 5.2 Geometric Isomers and the E/Z Naming System, 5.6 Compounds with More Than One Chirality Centers, 6.1 Electromagnetic Radiation and Molecular Spectroscopy, 6.3 IR Spectrum and Characteristic Absorption Bands, 6.6 H NMR Spectra and Interpretation (Part I), 6.7 H NMR Spectra and Interpretation (Part II), 7.1 Nucleophilic Substitution Reactions Overview, 7.2 SN2 Reaction Mechanisms, Energy Diagram and Stereochemistry, 7.3 Other Factors that Affect SN2 Reactions, 7.4 SN1 Reaction Mechanisms, Energy Diagram and Stereochemistry, 7.6 Extra Topics on Nucleophilic Substitution Reactions, 8.4 Comparison and Competition Between SN1, SN2, E1 and E2, 9.5 Stereochemistry for the Halogenation of Alkanes, 9.6 Synthesis of Target Molecules: Introduction to Retrosynthetic Analysis, 10.2 Reactions of Alkenes: Addition of Hydrogen Halide to Alkenes, 10.3 Reactions of Alkenes: Addition of Water (or Alcohol) to Alkenes, 10.4 Reactions of Alkenes: Addition of Bromine and Chlorine to Alkenes, 10.6 Two Other Hydration Reactions of Alkenes.