EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 4, Problem 4.21P
Interpretation Introduction
Interpretation:
The product of the reaction of
Concept introduction:
Carbocations are the reaction intermediates and they contain the electron deficient positively charged carbon atom. The electron deficient carbon is
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Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene
constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene
products. Offer an explanation for this difference.
Describe and provide a detailed mechanism (use arrow pushing) for the preparation of 2-methyl- 1-butene and 2-methyl-2-butene
Write
an equation(s) to illustrate the mechanism
for the dehydrohalogenation of
2-bromo-2-methylbutane. Give the major product expected from the mechanism and use arrows
to indicate electron flow.
Why is this reaction referred to as a concerted process?
Chapter 4 Solutions
EBK ORGANIC CHEMISTRY
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - Prob. 4.3PCh. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Prob. 4.8PCh. 4 - Prob. 4.9PCh. 4 - Prob. 4.10P
Ch. 4 - Prob. 4.11PCh. 4 - Prob. 4.12PCh. 4 - Prob. 4.13PCh. 4 - Prob. 4.14PCh. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Prob. 4.17PCh. 4 - Prob. 4.18PCh. 4 - Prob. 4.19PCh. 4 - Prob. 4.20PCh. 4 - Prob. 4.21PCh. 4 - Prob. 4.22PCh. 4 - Prob. 4.23PCh. 4 - Prob. 4.24PCh. 4 - Prob. 4.25PCh. 4 - Prob. 4.26PCh. 4 - Prob. 4.27PCh. 4 - Prob. 4.28PCh. 4 - Prob. 4.29PCh. 4 - Prob. 4.30PCh. 4 - Prob. 4.31PCh. 4 - Prob. 4.32PCh. 4 - Prob. 4.33PCh. 4 - Prob. 4.34PCh. 4 - Prob. 4.35PCh. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Prob. 4.39PCh. 4 - Prob. 4.40APCh. 4 - Prob. 4.41APCh. 4 - Prob. 4.42APCh. 4 - Prob. 4.43APCh. 4 - Prob. 4.44APCh. 4 - Prob. 4.45APCh. 4 - Prob. 4.46APCh. 4 - Prob. 4.47APCh. 4 - Prob. 4.48APCh. 4 - Prob. 4.49APCh. 4 - Prob. 4.50APCh. 4 - Prob. 4.51APCh. 4 - Prob. 4.52APCh. 4 - Prob. 4.53APCh. 4 - Prob. 4.54APCh. 4 - Prob. 4.55APCh. 4 - Prob. 4.56APCh. 4 - Prob. 4.57APCh. 4 - Prob. 4.58APCh. 4 - Prob. 4.59APCh. 4 - Prob. 4.60APCh. 4 - Prob. 4.61APCh. 4 - Prob. 4.62APCh. 4 - Prob. 4.63APCh. 4 - Prob. 4.64APCh. 4 - Prob. 4.65APCh. 4 - Prob. 4.66APCh. 4 - Prob. 4.67APCh. 4 - Prob. 4.68APCh. 4 - Prob. 4.69APCh. 4 - Prob. 4.70AP
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- Based on what you know about the relative stabilities of alkyl cations and benzyliccations, predict the product of addition of HBr to 1-phenylpropenearrow_forward(c) Alkenes can be transformed into epoxides by an epoxidation reaction. If the following hexenes are all subjected to an epoxidation reaction, which one would give an achiral epoxide? Explain your answer. 1-hexene cis-2-hexene trans-2-hexene cis-3-hexene trans-3-hexenearrow_forwardWrite the mechanism of the reaction of trans-2-butene with hydrogen bromide.arrow_forward
- What products will be obtained mainly by nitration of 2-methylbutane? Write a reaction scheme and indicate the reaction conditionsarrow_forwardGive the structure(s) of the organic product(s) that would result from dehydrohalogenation of 1-iodo-1-methylyclohexane. If more than one structure is possible, indicate which is the major product.arrow_forwardLike other hydroborations, the reaction of alkynes with catecholborane is a syn addition and its regioselectivity is opposite to Markovnikov’s rule.Use this fact to outline a synthesis of the compound shown from 1-hexyne and (Z)-C6H5CH=CHBr.arrow_forward
- Use line structures and write the mechanism for the first and second steps of the hydrobromination reaction of compound C in the presence of HBr to demonstrate that it is a regioselective reaction. Clearly indicate the following: a) the flow electrons in step 1 and in step 2 and b) draw the product D(product 2) resulting from step 2. Include stereo chemistry in your answer.arrow_forwardPart A: Please explain in detail the mechanism of catalytic hydrogenation when applied to the reactants, (Z)-3-methyl-2-hexene and hydrogen gas, with the catalyst, Ni-C. Part B: What are the product(s) of this reaction?arrow_forwardPredict the structure of the major product formed by 1,2-addition of HCl to 2-methyl-1,3-butadiene (isoprene).arrow_forward
- a) Cycohexanone reacts with 1,3-propanediol under acid catalysis to form the cyclic acetal. Write down the reaction mechanism and explain why the use of cyclic acetals as protecting groups is preferred over open- chain acetals. b) Eugenol (see below) is made from cloves. Give the structural formulas of the products which are formed after reaction of eugenol with i) BH3, then H2O2 / NaOH or after reaction with ii) acetic anhydride. OH Eugenolarrow_forwardCH3 Br,/FeBr3 C3H;BrO 5 Using resonance structures, justify whether the acetyl group of compound 5 will direct the bromination reaction to the meta or ortho/para positions.arrow_forwardThe following compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards P-elimination reaction.arrow_forward
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