Organic Chemistry (Binghampton University)
16th Edition
ISBN: 9781308795010
Author: Carey
Publisher: MCG CUSTOM
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Chapter 10.5, Problem 10P
Interpretation Introduction
Interpretation:
The “normal” and “abnormal” products formed in the reaction of allyl bromide with hydrogen bromide under a variety of conditions are to be identified. Out of these two products, the product that is the result of addition in accordance with Markovnikov's rule and the one which corresponds to addition opposite to the Markovnikov's rule is to be given.
Concept introduction:
Addition of hydrogen halides to
This addition may be electrophilic, which proceeds through the formation of carbocation intermediates.
During electrophilic addition, a proton is added to the double bond such that the more stable carbocation is produced.
The overall addition is according to the Markovnikov rule. The hydrogen atoms get added to the carbon atom, which has more hydrogens attached to it.
The addition of hydrogen halides to alkenes may be through the formation of free radicals as intermediates.
During free radical addition, the bromine is added to the double bond such that a more stable alkyl free radical is produced.
The overall addition takes place with a regioselectivity opposite to that of Markovnikov rule: The hydrogen atoms get added to the carbon atom which has less hydrogens attached to it.
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The carbocation electrophile in a Friedel-Crafts reaction can be generated in ways other than by reaction of an alkyl chloride with AlCl3. For example, reaction of benzene with 2-methylpropene in the presence of H3PO4 yields tert-butylbenzene. Draw a structure for the electrophile.
What reaction scheme would have
- and electrophillic addition
- the use of NaBH4 or LiAlH4
- a reaction that generates a new stereocentre
- 2-methylbutan-1-ol
Use the extended version of Markovnikov’s rule to predict the regiochemistry (orienta- tion) of electrophilic additions to alkenes.
Chapter 10 Solutions
Organic Chemistry (Binghampton University)
Ch. 10.1 - Prob. 1PCh. 10.1 - Prob. 2PCh. 10.2 - Use the data in Table 10.1 to calculate H for the...Ch. 10.3 - Prob. 4PCh. 10.4 - Prob. 5PCh. 10.4 - Prob. 6PCh. 10.4 - Do the arithmetic involved in converting the...Ch. 10.4 - How many constitutionally isomeric...Ch. 10.4 - Prob. 9PCh. 10.5 - Prob. 10P
Ch. 10.5 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 13PCh. 10.7 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10 - Carboncarbon bond dissociation enthalpies have...Ch. 10 - Use the bond dissociation enthalpy data in Table...Ch. 10 - Use the bond dissociation enthalpy data in Table...Ch. 10 - Write the structure of the major organic product...Ch. 10 - Excluding enantiomers, free-radical chlorination...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - Compound A (C6H14) gives three different...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Prob. 29PCh. 10 - Guiding your reasoning by retrosynthetic analysis,...Ch. 10 - (Z)-9-tricosene [(Z)-CH3(CH2)7CH=CH(CH2)12CH3] is...Ch. 10 - Prob. 32PCh. 10 - Prob. 33PCh. 10 - Prob. 34DSPCh. 10 - Prob. 35DSPCh. 10 - Prob. 36DSPCh. 10 - Prob. 37DSPCh. 10 - Prob. 38DSP
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