Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 2.SE, Problem 27MP
Double bonds can also act like Lewis bases, sharing their electrons with Lewis acids. Use curved arrows to show how each double bond below will react with HCl and draw the resulting carbocation.
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In the following acid - base reactions, a) Draw Lewis structures of the reactants and the products. b)
Determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases).
c) Use the curved - arrow formalism to show the movement of electron pairs in these reactions and the
imaginary movement in the resonance hybrids of the products. d) Indicate which reactions are best
termed Brønsted-Lowry acid - base reactions i. CH3CHO + HCI--
> CH3CH2O
+ + Cl- ii. CH3CHO + OH- - -
> CH3CO-(OH) H
Draw structural formulas for organic products A and B in the window below.
Mg
H20
A
H3CC=CH2
ether
Br
• Draw only products having the organic portion of the original alkyl halide.
• Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium.
• Separate products from different steps using the → sign from the drop-down menu.
Be sure to answer all parts.
Draw the product of the Lewis acid-base reaction. Label the electrophile and nucleophile.
CH,CH,OH + BF,
window open
nucleophile v electrophile
Chapter 2 Solutions
Organic Chemistry
Ch. 2.1 - Prob. 1PCh. 2.1 - Prob. 2PCh. 2.1 - Use the electronegativity values shown in Figure...Ch. 2.1 - Look at the following electrostatic potential map...Ch. 2.2 - Ethylene glycol, HOCH2CH2OH, may look nonpolar...Ch. 2.2 - Make three-dimensional drawings of the following...Ch. 2.3 - Calculate formal charges for the nonhydrogen atoms...Ch. 2.3 - Organic phosphate groups occur commonly in...Ch. 2.6 - Which of the following pairs of structures...Ch. 2.6 - Draw the indicated number of resonance forms for...
Ch. 2.7 - Nitric acid (HNO3) reacts with ammonia (NH3) to...Ch. 2.8 - Prob. 12PCh. 2.8 - Amide ion, H2N-, is a much stronger base than...Ch. 2.9 - Prob. 14PCh. 2.9 - Prob. 15PCh. 2.9 - Prob. 16PCh. 2.11 - Using curved arrows, show how the species in part...Ch. 2.11 - Prob. 18PCh. 2.12 - Of the two vitamins A and C, one is hydrophilic...Ch. 2.SE - Prob. 20VCCh. 2.SE - The following model is a representation of...Ch. 2.SE - cis-l, 2-Dichloroethylene and trans-1,...Ch. 2.SE - The following molecular models are representations...Ch. 2.SE - Predict the product(s) of the acid/base reactions...Ch. 2.SE - Use curved arrows to draw the protonated form of...Ch. 2.SE - Prob. 26MPCh. 2.SE - Double bonds can also act like Lewis bases,...Ch. 2.SE - Prob. 28APCh. 2.SE - Use the electronegativity table given in Figure...Ch. 2.SE - Which of the following molecules has a dipole...Ch. 2.SE - Prob. 31APCh. 2.SE - Phosgene, C12C=O, has a smaller dipole moment than...Ch. 2.SE - Prob. 33APCh. 2.SE - Methanethiol, CH3SH, has a substantial dipole...Ch. 2.SE - Calculate the formal charges on the atoms shown in...Ch. 2.SE - Assign formal charges to the atoms in each of the...Ch. 2.SE - Which of the following pairs of structures...Ch. 2.SE - Prob. 38APCh. 2.SE - 1, 3-Cyclobutadiene is a rectangular molecule with...Ch. 2.SE - Alcohols can act either as weak acids or as weak...Ch. 2.SE - The O-H hydrogen in acetic acid is more acidic...Ch. 2.SE - Draw electron-dot structures for the following...Ch. 2.SE - Write the products of the following acid-base...Ch. 2.SE - Rank the following substances in order of...Ch. 2.SE - Which, if any, of the substances in Problem 2-44...Ch. 2.SE - The ammonium ion (NH4+, pKa = 9.25) has a lower...Ch. 2.SE - Prob. 47APCh. 2.SE - Prob. 48APCh. 2.SE - Calculate Ka values from the following pka’s:...Ch. 2.SE - Calculate pKa values from the following Ka’s:...Ch. 2.SE - What is the pH of a 0.050 M solution of formic...Ch. 2.SE - Prob. 52APCh. 2.SE - Maleic acid has a dipole moment, but the closely...Ch. 2.SE - Assume that you have two unlabeled bottles, one of...Ch. 2.SE - Identify the acids and bases in the following...Ch. 2.SE - Which of the following pairs represent resonance...Ch. 2.SE - Draw as many resonance structures as you can for...Ch. 2.SE - Carbocations, which contain a trivalent,...Ch. 2.SE - We’ll see in the next chapter that organic...Ch. 2.SE - The azide functional group, which occurs in...Ch. 2.SE - Phenol, C6H5OH, is a stronger acid than methanol,...Ch. 2.SE - Thiamin diphosphate (TPP), a derivative of vitamin...Ch. 2.SE - Determine if each compound or ion below has a...Ch. 2.SE - Prob. 64APCh. 2.SE - Prob. 65APCh. 2.SE - Draw the conjugate base for each compound below...Ch. 2.SE - 1, 1, 1-Trichloroethanol is an acid more than 1000...
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- What is hydrolysis? Group of answer choices It is a reaction that involves the formation of water. It is the reaction that has water as a reactant, and involves the breaking of bonds in the water molecule. It is the solvation of a species in water. It is the reaction of a base with an acid. It is the phase change of water from a solid to a liquid.arrow_forward6. Classify each acid base reaction as a Brønsted or Lewis pair. Label the acid (or electrophile) and the base (or nucleophile). Draw a curved arrow to show how electrons moved to form the new bond(s). i CH3Li -H + Na + CH3Li NaNH, OH Br H3C- O Lit O Lit 핸 Na CH4 NH3 + NaBrarrow_forwardWe don't see the answer written with a photo or pen, give the answer using the toolarrow_forward
- Ethanol (CH3CH2OH) is an example of a compound with an alcohol group. Alcohols can act as acids or bases in solution. We can consider a reaction of ethanol with NaOH to see the acid/base properties. a. Draw Lewis structures of ethanol and sodium hydroxide. Be sure to show all lone pairs and formal charges. ethanol sodium hydroxide b. Draw out a full equilibrium acid/base reaction between ethanol and sodium hydroxide, showing the correct arrows for electron movement. Use the pka table at the right to answer the following questions. C. What would you expect the equilibrium composition of this reaction to be? d. If a chemist wanted to push the reaction to create a high yield of product, what would be a good base to use? Short pKa table Functional group Alkane Amine Alkyne Water Protonated amines. Carboxylic acids Hydrochloric acid Example CH₁ :NH₂ R=H HO-H NHA CI H₂C OH HCI Weaker acid pKa ~50 -35 25 16 10 5 -8arrow_forwardPLS HELP ASAP ON ALL ASKED QUESTIONS PLSarrow_forward7. (Chapters 6 and 8) Within the following set, which is more stable, and why? CH3 CH3 H3C- -C=CH- CH2 H2C=Ć- -CH CH3 8. (Chapter 12) What type of instability will an intermediate need to address following the reaction of a nucleophile/base that has a negative charge with a pi bond that has uneven electron distribution between atoms with different electronegativities (C=O)? 9. (Chapter 9) Circle the carbon that will be unstable in the intermediate of the following reaction. Then, state the reason for your choice, and also indicate what type of instability it will be. H,C-CH,- C ECH with NaNH2 10. (Chapters 12 and 13) What are three sources used to provide electrons to an electron-deficient carbon with a leaving group? 1. 2. 3.arrow_forward
- 4. Using structures for all species, write the complete esterification reaction begun below: HSO, methanol (CH3OH) + salicylic acidarrow_forwardPredict te organic product that forms in the reaction below: H Xy+ OH H+ OH H+ Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the product. In the drawing area below, draw the skeletal ("line") structure of the missing organic product X. Click and drag to start drawing a structure.arrow_forwardDraw structural formulas for organic products A and B in the window below. ● -CI ** Li pentane Draw only products having the organic portion of the original alkyl halide. Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. Separate products from different steps using the → sign from the drop-down menu. ? H₂O 000- FIF [F ChemDoodleⓇ Barrow_forward
- Draw structural formulas for organic products A and B in the window below. -CI Li pentane H₂O A B • Draw only products having the organic portion of the original alkyl halide. • Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. • Separate products from different steps using the →>> sign from the drop-down menu. ? n [ ChemDoodleⓇarrow_forwardComplete the reactionarrow_forward4. Draw the structure and name the first ten (10) members of Acid Halides using bromine as the halide.arrow_forward
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