Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 11, Problem 11.49P
Interpretation Introduction
Interpretation: A mechanism for the reaction of
Concept Introduction: The replacement or substitution of one
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Treatment of alkenes A and B with HBr gives the same alkyl halide C. Draw a mechanism for each reaction, including all
reasonable resonance structures for any intermediate.
Br
-CHCH2CH,
HBr
HBr
-CH=CHCH,
-CH2CH=CH2
A
B.
2- Mention the product of a nucleophilic substitution reaction of (S)-2-bromohexane with acetate ion, CH3CO2- Assume that inversion of configuration occurs, and show the chemistry of both the reactant and product. 3- Draw the mechanism of the SN2 Reaction. Show the correct directions of the arrows, and all reagents. 4- Draw the mechanism of the SN1 Reaction. Show the correct directions of the arrows, and all reagents. 5- Draw the mechanism of the E2 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 6- Draw the mechanism of the E1 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 7- Mention the product formed in an SN2 reaction between 1-bromobutane and NaI. 8- Rank the following compounds in order of their expected reactivity toward SN2 reaction: CH3Br, CH3OTos, (CH3)2CHCl. 9- Explain Grignard Reagents in details with one example. 10- Mention how a halogen substituent can be replaced by a deuterium atom…
List all alkene products for each reaction. Write a mechanism for the
formation of each product following E1 or E2 mechanisms as appropriate. Be
sure to draw arrows for the mechanism.
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Draw structures for the three alkynes having...Ch. 11 - Prob. 11.2PCh. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.5PCh. 11 - Prob. 11.6PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Prob. 11.9PCh. 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. 11.13PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.19PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.21PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.23PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.25PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - Prob. 11.27PCh. 11 - Give the IUPAC name for each alkyne.Ch. 11 - Prob. 11.29PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.31PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - Draw the products formed when 3-hexyne is treated...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - What alkynes give each of the following ketones as...Ch. 11 - Prob. 11.41PCh. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - Prob. 11.43PCh. 11 - Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.52PCh. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - Prob. 11.55PCh. 11 - Synthesize each compound from acetylene. You may...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.61PCh. 11 - Prob. 11.62PCh. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.65PCh. 11 - Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.67PCh. 11 - 11.65 Explain why an optically active solution of ...
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- Treatment of cis-2-bromocyclohexanol with NaOH yields cyclohexanone instead of an epoxide. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism.arrow_forwardDraw a plausible mechanism for the following reactions, showing relevant lone pairs and arrow pushing. Do not consider stereochemistry in your mechanism. a) H,SO4, EtOH b) OH H,SO, Heatarrow_forwardThe following product can be synthesized from the reaction of an alkene with Hg(OAc)2 followed by reduction with NaBH4. Draw all possible alkenes that will give the product shown.arrow_forward
- What is the major substitution product for the following reaction? Show the mechanism for the reaction.arrow_forwardDraw the products formed when the following alkynes are treated with each set of reagents: [1] H2O, H2SO4, HgSO4; or [2] R2BH followed by H2O2, −OH.arrow_forwardComplete the following reactions by providing the missing product(s). Determine what mechanism operates in each case (SN1, Sn2, E1, or E2), Show the stereochemistry of the product(s) where appropriate. If more than one product us formed circle the major one. Br H,O Br NaOCH;CH;arrow_forward
- What is the major elimination product obtained from the following reaction? CH3 CH3 NaOCH₂CH3 HOCH₂CH3 Ot-Bu || CH3 Ot-Bu ||| CH3 IV CH3arrow_forwardWhat alkene is needed to synthesize each 1,2-diol using [1] OsO4 followed by NaHSO3 in H2O; or [2] CH3CO3H followed by −OH in H2O?arrow_forwardComplete the following reactions by providing the missing product(s). Determine what mechanism operates in each case (SN1, Sn2, E1, or E2), Show the stereochemistry of the product(s) where appropriate. If more than one product us formed circle the major one. KCN Br NaOCH2CH3 Brarrow_forward
- Using cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecic reaction. Draw the structure of the stereoisomers formed from each alkene.arrow_forwardWhen cyclohexene is treated with m-chloroperbenzoic acid and H,0, trans-cyclohexane-1,2-diol is produced. Propose a mechanism for this reaction, accounting for the observed stereochemistry. Hint: Recall what a МСРВА + Enantiomer H2O "OH peroxyacid does to an alkene.arrow_forward2) Below are the products of 2 different reactions with alkenes. Draw the structure of the alkene starting material for each product and assume no carbocation rearrangements H-Br Cl₂ Br CI CIarrow_forward
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