Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 8, Problem 8.45P
Interpretation Introduction
Interpretation:
The cis isomer of
Concept introduction:
The
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The rate of bromination of the following three alkenes: 2-methyl-1-pentene, 2-methyl-2-pentene, 3-methyl-1-pentene. Please rank them in order from slowest to fastest to react.
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In an E2 mediated elimination reaction of an alkyl halide (H-X) using NaOCH3 as
base, which of the following statement is not true?
O The reactivity order for alkyl halides (RX) is tertiary secondary> primary.
O The rate of reaction = k2 (alkyl halide] [NaOCH₂]
O The reaction occurs in a single step.
O The rate is independent of the leaving group.
The rate of bromination of the following three alkenes is very different: 2-methyl-1-pentene, 2-methyl-2-pentene, 3-methyl-1-pentene. Rank them in order from slowest to fastest to react.
Chapter 8 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 8 - Prob. 8.1PCh. 8 - Prob. 8.2PCh. 8 - Prob. 8.3PCh. 8 - Prob. 8.4PCh. 8 - Prob. 8.5PCh. 8 - Prob. 8.6PCh. 8 - Prob. 8.7PCh. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10P
Ch. 8 - Prob. 8.11PCh. 8 - Prob. 8.12PCh. 8 - Prob. 8.13PCh. 8 - Prob. 8.14PCh. 8 - Prob. 8.15PCh. 8 - Prob. 8.16PCh. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Prob. 8.20PCh. 8 - Prob. 8.21PCh. 8 - Prob. 8.22PCh. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - Prob. 8.25PCh. 8 - Prob. 8.26PCh. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Prob. 8.29PCh. 8 - Prob. 8.30PCh. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - Prob. 8.34PCh. 8 - Prob. 8.35PCh. 8 - Prob. 8.36PCh. 8 - Prob. 8.37PCh. 8 - Prob. 8.38PCh. 8 - Prob. 8.39PCh. 8 - Prob. 8.40PCh. 8 - Prob. 8.41PCh. 8 - Prob. 8.42PCh. 8 - Prob. 8.43PCh. 8 - Prob. 8.44PCh. 8 - Prob. 8.45PCh. 8 - Prob. 8.46PCh. 8 - Prob. 8.47PCh. 8 - Prob. 8.48PCh. 8 - Prob. 8.49PCh. 8 - Prob. 8.50PCh. 8 - Prob. 8.51PCh. 8 - Prob. 8.52PCh. 8 - Prob. 8.53PCh. 8 - Prob. 8.54PCh. 8 - Prob. 8.55PCh. 8 - Prob. 8.56PCh. 8 - Prob. 8.57PCh. 8 - Prob. 8.58PCh. 8 - Prob. 8.59PCh. 8 - Prob. 8.60PCh. 8 - Prob. 8.61PCh. 8 - Prob. 8.62PCh. 8 - Prob. 8.63PCh. 8 - Prob. 8.64PCh. 8 - Prob. 8.65PCh. 8 - Prob. 8.66PCh. 8 - Prob. 8.67PCh. 8 - Prob. 8.68PCh. 8 - Prob. 8.69PCh. 8 - Prob. 8.70PCh. 8 - Prob. 8.71PCh. 8 - Prob. 8.72PCh. 8 - Prob. 8.73PCh. 8 - Prob. 8.74PCh. 8 - Prob. 8.75PCh. 8 - Prob. 8.76PCh. 8 - Prob. 8.1YTCh. 8 - Prob. 8.2YTCh. 8 - Prob. 8.3YTCh. 8 - Prob. 8.4YTCh. 8 - Prob. 8.5YTCh. 8 - Prob. 8.6YTCh. 8 - Prob. 8.7YTCh. 8 - Prob. 8.8YTCh. 8 - Prob. 8.9YTCh. 8 - Prob. 8.10YTCh. 8 - Prob. 8.11YTCh. 8 - Prob. 8.12YTCh. 8 - Prob. 8.13YTCh. 8 - Prob. 8.14YTCh. 8 - Prob. 8.15YTCh. 8 - Prob. 8.16YTCh. 8 - Prob. 8.17YTCh. 8 - Prob. 8.18YTCh. 8 - Prob. 8.19YT
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- Your task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents would you use? O KOH/H2O O KOH/CH,OH O CH3CH2ONA/CH3CH2OH O CH3ONA/CH3OH O (CH3)3COK/(CH3)3COHarrow_forwardFor SN1 Explain the order in which 1o (primary) alkyl halides reacted (fastest to slowest) and explain why. The 1o primary alkyl halides are: (see picture below) 1-chlorobutane 1-bromobutane 1-chloro-2butene benzylchloridearrow_forwardDraw the potential energy diagram of the reaction of 2-methylbut-1-ene with HBr, making sure you draw all reactants, products, intermediates, and transition states and label the rate- determining step.arrow_forward
- Write the mechanism of the following bromination reaction and explain the regioselectivity of the bromination reaction. Draw the mechanism, transition state, energy diagram, etc. The same reaction with chlorine is not much regioselective in Q1. Explain the decreased regioselectivity of the following chlorination reaction by comparing the bromination reaction in Q1. Draw the mechanism, transition state, energy diagram, etc.arrow_forward4. The cis isomer of 4-tert-butyl-1-bromocyclohexane undergoes E2 eliminations about 1,000 times faster than the trans isomer. Explain why the cis isomer reacts fast in complete sentences. (Hint: Draw the most stable chair structure of each; it is not because of steric hindrance.) Br Br NaOH FAST NaOH SLOWarrow_forwardThe nucleophile approaches from the opposite side of the carbon with the leaving group in which reaction mechanism? O E2 O SN1 O SN2 O SN1 and SN2arrow_forward
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- 5. Draw a detailed arrow pushing mechanism for the following reaction. Is the rate-determining step unimolecular (SN1) or bimolecular (SN2)? H aq. H-Br Br HOarrow_forwardDraw the mechanism for the following reaction and account for the relative stereochemistry. MeO₂C MeO₂C CO₂Me Pd2(dba)3.CHCI 3 Ph3P, ACOH MeO₂Carrow_forwardWhich of the following pairs of compounds reacts with OH- ions faster in an SN2 reaction? Briefly explain. CH3Br or CH3I? 2-chloro-2-methylpropane or chloromethane?arrow_forward
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