Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 6.SE, Problem 46AP
Ammonia reacts with acetyl chloride (CH3COCl) to give acetamide (CH3CONH2). Identify the bonds broken and formed in each step of the reaction, and draw curved arrows to represent the flow of electrons in each step.
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Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died.
Q.) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom?
Draw the complete Lewis structure of (CH3)2CHCH(NH2)CO2H and identify all H-bond donors and all H-bond acceptors.
Select the bonds in the 3D representation of methyl urethane below that are multiple bonds.
(Hint: Consider the number of bonds attached to an atom in the image compared to the normal valence of that atom. In a valid structure, the number of bonds to an atom will equal the valence of that atom.)
• Gray = C: white = H; red = 0; blue = N; dark green = Cl; brown = Br; light green = F; purple = 1; yellow = S: orange = P.
• Double click to select bonds.
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Chapter 6 Solutions
Organic Chemistry
Ch. 6.1 - Prob. 1PCh. 6.3 - Prob. 2PCh. 6.3 - Using curved fishhook arrows, propose a mechanism...Ch. 6.4 - Prob. 4PCh. 6.4 - An electrostatic potential map of boron...Ch. 6.5 - What product would you expect from reaction of...Ch. 6.5 - Reaction of HBr with 2-methylpropene yields...Ch. 6.6 - Prob. 8PCh. 6.6 - Predict the products of the following polar...Ch. 6.7 - Which reaction is more energetically favored, one...
Ch. 6.7 - Prob. 11PCh. 6.9 - Which reaction is faster, one with ∆G‡ = +45...Ch. 6.10 - Prob. 13PCh. 6.SE - Prob. 14VCCh. 6.SE - Prob. 15VCCh. 6.SE - Prob. 16VCCh. 6.SE - Look at the following energy diagram: (a) Is...Ch. 6.SE - Look at the following energy diagram for an...Ch. 6.SE - What is the difference between a transition state...Ch. 6.SE - Prob. 20EDRMCh. 6.SE - Prob. 21EDRMCh. 6.SE - Draw an energy diagram for a two-step exergonic...Ch. 6.SE - Draw an energy diagram for a reaction with keq =...Ch. 6.SE - The addition of water to ethylene to yield ethanol...Ch. 6.SE - When isopropylidenecyclohexane is treated with...Ch. 6.SE - Prob. 26EDRMCh. 6.SE - Draw the electron-pushing mechanism for each...Ch. 6.SE - Draw the complete mechanism for each polar...Ch. 6.SE - Prob. 29EDRMCh. 6.SE - Identify the functional groups in the following...Ch. 6.SE - Identify the following reactions as additions,...Ch. 6.SE - Identify the likely electrophilic and nucleophilic...Ch. 6.SE - For each reaction below identify the electrophile...Ch. 6.SE - Prob. 34APCh. 6.SE - Follow the flow of electrons indicated by the...Ch. 6.SE - Prob. 36APCh. 6.SE - Prob. 37APCh. 6.SE - Despite the limitations of radical chlorination of...Ch. 6.SE - Prob. 39APCh. 6.SE - Answer question 6-39 taking all stereoisomers into...Ch. 6.SE - Prob. 41APCh. 6.SE - Prob. 42APCh. 6.SE - Prob. 43APCh. 6.SE - The reaction of hydroxide ion with chloromethane...Ch. 6.SE - Prob. 45APCh. 6.SE - Ammonia reacts with acetyl chloride (CH3COCl) to...Ch. 6.SE - The naturally occurring molecule α-terpineol is...Ch. 6.SE - Prob. 48APCh. 6.SE - Prob. 49APCh. 6.SE - Draw the structures of the two carbocation...
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- Formation of ammonia from nitrogen and hydrogen is an exothermic process. Which of the following statements is true about the bonds that are broken and formed during this reaction? N2(g) + 3H2(g) ---> 2NH3(g) a.) products have lower PE because product bonds are weaker than reactants b.) products have higher PE because product bonds are stronger than reactants c.) products have higher PE because product bonds are weaker than reactants d.) products have lower PE because product bonds are stronger than reactantsarrow_forwardEstimate the heat released when 1-butene(CH3CH2CHCH2) reacts with bromine to give CH3CH2CHBrCH2Br. Bond enthalpies are CH : 412 kJ/mol; CC : 348 kJ/mol;CC : 612 kJ/mol; CBr : 276 kJ/mol;BrBr : 193 kJ/mol. 1.317 kJ/mol 2.507 kJ/mol 3.95 kJ/mol 4.288 kJ/mol 5.181 kJ/molarrow_forwardSodium triacetoxyborohydride, NaBH(OAc)3, is a mild reducing agent that reduces aldehydesmuch more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones,such as in the following reaction:CH3 C CH2O OC H CH3 C CH2OCH2OHNaBH(OAc)3CH3COOH(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydridearrow_forward
- We have thus far determined the single bond connectivity for (CH, ),CO as: H Н—с—с-—с—н H H There are six valence electrons still unaccounted. Carbon must form four bonds in order to satisfy the octet rule. Add a bond to carbon and fill in the remaining missing electrons. Select Draw Rings More H H. H H Harrow_forwardexplain which CO2 bond is shorter the one in methanol or the one in formaldehydearrow_forwardDraw a skeletal ("line") structure of this molecule: O CH3 HỌ—C—CH NH2arrow_forward
- The average bond energy (enthalpy) for a C=CC=C double bond is 614 kJ/molkJ/mol and that of a C−CC−C single bond is 348 kJ/molkJ/mol. Estimate the energy needed to break only the ππ bond of the double bond of 2-butene. Express your answer numerically in joules per molecule.arrow_forwardDraw the line-bond structure of oleic acid (cis-9-octadecenoic acid), CH3(CH2)7CH=CH(CH2)7COOH, at physiological pH. You do not need to draw hydrogen atoms attached to carbon atoms.arrow_forwardTwo useful organic compounds that contain Cl atoms are vinyl chloride (CH2 = CHCl) and chloroethane (CH3CH2Cl). Vinyl chloride is the starting material used to prepare poly(vinyl chloride), a plastic used in insulation, pipes, and bottles. Chloroethane (ethyl chloride) is a tica roman local anesthetic. Why is the C–Cl bond of vinyl chloride stronger than the C–Cl bond in chloroethane ?arrow_forward
- Two useful organic compounds that contain Cl atoms are vinyl chloride (CH2 = CHCl) and chloroethane (CH3CH2Cl). Vinyl chloride is the starting material used to prepare poly(vinyl chloride), a plastic used in insulation, pipes, and bottles.Chloroethane (ethyl chloride) is a tica roman local anesthetic. Why is the C–Cl bond of vinyl chloride stronger than the C–Cl bond in chloroethane ?arrow_forwardDraw the Lewis structure of acetic acid, CH3CO2H, clearly indicating all non-bonding pairs of electrons. Even though nitrogen and phosphorus have the same number of valence electrons, nitrogen can only bond to chlorine four times forming NCl4+ but phosphorus can bond with chlorine five times forming PCl5. Explain. Draw all the isomers of C4H9Br, using bond-line formulas. Draw the Lewis structure of the nitrite ion, NO2–, clearly indicating resonance contributors as well as non-bonding pairs of electrons and formal charges, as relevant. Nitromethane is a polar molecule but contains 2 equal polar covalent bonds. Briefly explain why and draw a relevant 3-dimensional structure to show the overall dipole moment of the molecule. Draw all isomers of C6H12O that are aldehydes.arrow_forwardFor a molecular formula of CsH6O: e a) Draw Lewis structures, showing all bonding and non-bonding electrons, for one compound with an alcohol functional group; one with an ether functional group; one with a ketone functional group; and one with an aldehyde functional group. For each compound, indicate all bond angles and build a molecular model. Indicate whether each pair of valence electrons is non-bonding (n) or o- or л-bonded. For each atom, indicate the corresponding orbitals that are involved (e.g. nsp3, osp3-sp3, etc.). b) c)arrow_forward
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