Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 9, Problem 3CTQ
Interpretation Introduction
Interpretation: The mechanism for the given reaction needs to be shown.
Concept Introduction: Halohydrin is formed when an
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The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve
negatively charged nucleophile, the attack of the nucleophile leads directly to the product.
H.
Br
+ CH3OH
Br
Intermediate 2
(product)
Intermediate 1
In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction.
OCH3
Cl2
MEOH
ĆI
racemic mixture
Pay attention to the reactants, they may differ from the examples. In some reactions, one part of the molecule acts as the nucleophile.
• You do not have to consider stereochemistry.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate intermediate 1 and intermediate 2 using the
the dropdown menu.
→ symbol from
What is an E2 mechanism? What are all of the steps, transition state, and all final products?
What are the characteristics of a good base for E2? How does a chemist tell a strong versus weak or bulky versus not bulky nucleophile?
Thank you
Consider the following reaction:
КОН
+ KBr
Br
OH
a) Does the reaction proceed via an SN1 or Sw2 mechanism?
b) Write out the mechanism for the reaction using curly arrows to show the formation of the
product from the starting material.
c) What general solvent type is best to use for this reaction?
d) Give a real example of such a solvent.
e) What would happen to the rate of the reaction if you doubled the concentration of KOH?
Chapter 9 Solutions
Organic Chemistry: A Guided Inquiry
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- 10. Write a detailed mechanism for the following reaction. Draw structures of the expected products. Label the MAJOR and MINOR products. Indicate the slow and fast steps. H-Br A + B + Carrow_forwardBr CH3OH + Br-Br H3CO The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product. +Br + CH3OH Br Intermediate 1 Intermediate 2 (product) In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OH + Br2 + HBr Br racemic mixture • Pay attention to the reactants, they may differ from the examples. In some reactions, one part of the molecule acts as the nucleophile. • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate intermediate 1 and intermediate 2 using the → symbol from the dropdown menu.arrow_forwardWhat is the mechanism for the entire reaction below?arrow_forward
- Give a complete mechanism for the intramolecular reaction below. You can leave the reaction protonated or add water at the last step to obtain the deprotonated product. OH Brarrow_forwardMECHANISM ACTIVITY Base-Induced Ester Hydrolysis (Saponification) NOC XT Step 1: Nucleophilic addition of hydroxide ion to the ester carbonyl group Ahrs MPR R16 H3C. R Part A (1 of 2) Draw the curved arrows for Step 1 of this mechanism. Arrow-pushing Instructions CH3 H-O: ÖH OR' :Ö H-O: O: H H H H 1x xxx CH3 CH3 Step 1 H3C. CH3 заarrow_forward8. Show the mechanism for the nucleophilic aromatic substitution below. NH2 Br NaNH, ZON + NaBr NO2arrow_forward
- Page of 11 ZOOM + Section A (continued) A10. Which of the following statements is true for an E1 reaction? The rate of an E1 elimination reaction of an alkyl halide depends on the concentration of: the alkyl halide only В A the base only the product the alkyl halide and base D A11. Identify the main product for the following Sn2 reaction. Br NaSEt main product ? A В SEt Br ŞEt SEt A12. Which reagent should be chosen to carry out the following reaction? A MCPBA KMNO4 CrO3 in H2SO4 D HCI in H2O A13. Which of the following is the strongest base? A В H .N. H ZHNarrow_forward1. Write a complete mechanism for the reaction shown below. Show all steps and electron- pushing arrows for each step. Br₂ H₂O 2. Using the same starting compound as #1 but this time use HBr and H2O, instead of using Br2 and H2O. Write a complete mechanism for the reaction.arrow_forward3. Use the reaction shown below to answer parts a-b. OH H20 HBr Br a. Compare the structure of the starting material to the product. Based on the changes you observe, which mechanisms take place during the reaction? Circle all that apply. Sy2 SN1 E1 E2 Acid/Base Radical Halogenation b. Draw the arrow-pushing mechanism that explains the formation of the products shown below. One mechanistic step should be shown per box; you will use all boxes. (Hint: Carbocation rearrangement.) Step 1 Products ОН H20 Br Br-H Step 2 Step 5 Step 3 Step 4arrow_forward
- For each reaction below identify the electrophile and the nucleophile.arrow_forwardIn both examples below the reactants shown are combined to bring about a nucleophilic substitution (SN1, SN2) and/or elimination (E1, E2) reaction. What is the major reaction that takes place in each case? BrCH₂COCH3 CH3 CH3CH₂CCH3 NaCN CH3OH H₂O SN2 Marrow_forwardMacmillan Learning Use the table of bond dissociation energies to calculate and compare the enthalpy of monobromination and monochlorination for the given alkyl position. Bond Dissociation Energies (for A-B- A+B) Bond broken H-H Br-Br CI-CI CH₂CH₂CH₂-H+ Br₂ CH₂CH₂CH₂-H + Cl₂ AH (kJ/mol) Bond broken AH (kJ/mol) 436 366 193 432 243 H-Br H-Cl CH₂CH₂CH₂-Br + HBr CH₂CH₂CH₂-CI+HCI Bond broken AH (kJ/mol) CH₂CH₂CH₂-H 423 CH₂CH₂CH₂-Br 294 CH₂CH₂CH₂-CI 354 AH = ΔΗ = -58 Incorrect -131 Incorrect kJ/mol kJ/molarrow_forward
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