ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 15.24P
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Q4: Rank the relative nucleophilicity of halide ions in water solution and DMF solution,
respectively.
F CI
Br |
Q5: Determine which of the substrates will and will not react with NaSCH3 in an SN2 reaction to
have a reasonable yield of product.
NH2
Br
Br
Br
OH
Br
Q7: Rank the following groups in order of basicity, nucleophilicity, and leaving group ability.
a) H₂O, OH, CH3COOT
b) NH3, H₂O, H₂S
Q8: Rank the following compounds in order of increasing reactivity in a nucleophilic substitution
reaction with CN as the nucleophile.
Br
A
B
NH2
LL
F
C
D
OH
CI
LLI
E
Q9: Complete the missing entities for following reactions (e.g., major product(s), reactants,
and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for
reactions a) to d).
a)
H
"Cl
D
+
-OCH 3
Page 3 of 5
Chapter 15 Solutions
ORGANIC CHEMISTRY
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Prob. 15.7PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Draw the products of each reaction.
a. b. c.
Ch. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Problem 15.20 Which compounds can be prepared in...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15.35 What is the major monobromination product...Ch. 15 - Prob. 15.36PCh. 15 - 15.37 What alkane is needed to make each alkyl...Ch. 15 - 15.38 Which alkyl halides can be prepared in good...Ch. 15 - Prob. 15.39PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.42PCh. 15 - 15.43 Draw the products formed when each alkene is...Ch. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - 15.45 Draw the organic products formed in each...Ch. 15 - Prob. 15.46PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - 15.48 Draw the products formed in each reaction...Ch. 15 - Prob. 15.49PCh. 15 - 15.50 Draw all the monochlorination products that...Ch. 15 - Prob. 15.51PCh. 15 - 15.52 (a) Draw the products (including...Ch. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - 15.57 Devise a synthesis of each compound from...Ch. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - 15.60 Devise a synthesis of each compound using ...Ch. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.69PCh. 15 - Prob. 15.70PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.73PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.75PCh. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.77PCh. 15 - Prob. 15.78PCh. 15 - Prob. 15.79P
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- Q10: (a) Propose a synthesis of C from A. (b) Propose a synthesis of C from B. Br Br ...\SCH 3 A B Carrow_forward9: Complete the missing entities for following reactions (e.g., major product(s), reactants, and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for reactions a) to d).arrow_forwardComplete the missing entities for following reactions (e.g., major product(s), reactants, and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for reactions a) to d).arrow_forward
- QUESTION 3: Provide the synthetic steps that convert the starting material into the product (no mechanism required). HO OH NH CH3 multiple steps 요요 H3Carrow_forwardQ6: Predict the effect of the changes given on the rate of the reaction below. CH3OH CH3Cl + NaOCH3 → CH3OCH3 + NaCl a) Change the substrate from CH3CI to CH31: b) Change the nucleophile from NaOCH 3 to NaSCH3: c) Change the substrate from CH3CI to (CH3)2CHCI: d) Change the solvent from CH3OH to DMSO.arrow_forwardQ3: Arrange each group of compounds from fastest SN2 reaction rate to slowest SN2 reaction rate. a) CI Cl فيكم H3C-Cl A B C D Br Br b) A B C Br H3C-Br Darrow_forward
- Q2: Group these solvents into either protic solvents or aprotic solvents. Acetonitrile (CH3CN), H₂O, Acetic acid (CH3COOH), Acetone (CH3COCH3), CH3CH2OH, DMSO (CH3SOCH3), DMF (HCON(CH3)2), CH3OHarrow_forwardSuppose the rate of evaporation in a hot, dry region is 1.76 meters per year, and the seawater there has a salinity of 35 ‰. Assuming a 93% yield, how much salt (NaCl) can be harvested each year from 1 km2 of solar evaporation ponds that use this seawater as a source?arrow_forwardhelparrow_forward
- Explain why only the lone pairs on the central atom are taken into consideration when predicting molecular shapearrow_forward(ME EX1) Prblm #9/10 Can you explain in detail (step by step) I'm so confused with these problems. For turmber 13 can u turn them into lewis dot structures so I can better understand because, and then as well explain the resonance structure part. Thanks for the help.arrow_forwardProblems 19 and 20: (ME EX1) Can you please explain the following in detail? I'm having trouble understanding them. Both problems are difficult for me to explain in detail, so please include the drawings and answers.arrow_forward
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