Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 11, Problem 11.59P
N-Chlorosuccinimide (NCS) serves as a source of
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Answer the following questions involving organic synthesis:
c.) Write a reasonable forward synthesis for the conversion of 2-bromopentane to ethyl methyl ether.
d.) Write any reaction with an alkene that occurs via a syn addition and draw its transition state.
e.) Write any reaction with an alkene that occurs via an anti addition and draw its transition state.
f.) Define Markovnikov’s rule and write out two reactions: one that is a Markovnikov addition and another that is an anti-Markovnikov pathway.
When 3-bromo-2,3-dimethylbutane is heated in sodium tert-butoxide, one major alkene is formed. In Part 1, draw this major alkene and all byproducts. In Part 2, indicate what type of mechanism leads to the formation of the alkene drawn in Part 1.
1. What is it's type of reaction (Sn1, Sn2, E1, E2, Nucleophilic Addition, Nucleophilic Acyl Substition or Redox reaction)
2. What is it's major product.
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Problem 11.1 Neopheliosyne B is a novel acetylenic...Ch. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.4PCh. 11 - Prob. 11.5PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Draw additional resonance structures for each...Ch. 11 - Problem 11.9 Draw the products formed when is...Ch. 11 - Explain the following result. Although alkenes...
Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.12PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.14PCh. 11 - Problem 11.15 Draw the organic products formed in...Ch. 11 - Problem 11.16 What acetylide anion and alkyl...Ch. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.18PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.20PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.22PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.24PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - 11.26 Give the IUPAC name for each alkyne.
a. ...Ch. 11 - Prob. 11.27PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.29PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - What reagents are needed to convert (CH3CH2)3CCCH...Ch. 11 - Prob. 11.35PCh. 11 - 11.36 What alkynes give each of the following...Ch. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - 11.38 Draw the organic products formed in each...Ch. 11 - 11.39 Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.43PCh. 11 - Prob. 11.44PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - 11.46 Tautomerization in base resembles...Ch. 11 - 11.47 Draw a stepwise mechanism for each...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.50 What acetylide anion and alkyl halide are...Ch. 11 - 11.51 Synthesize each compound from acetylene. You...Ch. 11 - 11.52 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.59 N-Chlorosuccinimide (NCS) serves as a source...Ch. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - 11.61 Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.62PCh. 11 - 11.63 Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.64PCh. 11 - 11.65 Explain why an optically active solution of ...
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- When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2) groups are substituted for hydrogens at the 2, 4 and 6 positions on the ring (the next section discusses why the 2, 4, and 6 positions are substituted). The product is a highly explosive substance called 2,4,6-trinitrotoluene. This subastance is commonly known by a three letter name. What is it?arrow_forwardComplete the following reactions with the product or reagent as appropriatearrow_forwardWhat three alkenes (excluding stereoisomers) can be used to prepare 3-chloro-3-methylhexane by addition of HCl?arrow_forward
- What is the major product between the reaction of 2-methoxypentane and HBr reagent?arrow_forwardUse the two starting materials in each question as the only sources of carbon. React them with any reagents necessary to assemble the desired moleculearrow_forwardExplain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and D, respectively.arrow_forward
- Axial alcohols are oxidized faster than equatorial alcohols by PCC and other Cr6+ oxidants. Which OH group in each compound is oxidized faster?arrow_forwardDraw the possible products of this epoxied ring opening reaction. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers, Ignore any inorganic byproducts.arrow_forwardAnswer the following questions involving organic synthesis: a.) Propose a forward synthesis of an alkyne from an alkene starting material. b.) Develop a forward synthesis of an epoxide from 1-chloropropane. c.) Write a reasonable forward synthesis for the conversion of 2-bromopentane to ethyl methyl ether. d.) Write any reaction with an alkene that occurs via a syn addition and draw its transition state. e.) Write any reaction with an alkene that occurs via an anti addition and draw its transition state. f.) Define Markovnikov’s rule and write out two reactions: one that is a Markovnikov addition and another that is an anti-Markovnikov pathway.arrow_forward
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