Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 8, Problem 8.46P
Interpretation Introduction
Interpretation: The isomer of 1-bromo-4-tert-butylcyclohexane which reacts faster in an E2 reaction is to be predicted.
Concept introduction: The essential condition for E2 elimination is the anti-periplanar geometry of the leaving groups.
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Does cis- or trans-1-bromo-4-tert-butylcylohexane react faster in an E2reaction?
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Which bromocyclohexane starting material would react faster – the cis or trans, and explain why? Draw both chair forms of the starting material to prove your point.
Chapter 8 Solutions
Organic Chemistry
Ch. 8 - Problem 8.1 Label the and carbons in each alkyl...Ch. 8 - Problem 8.2 Classify each alkene in the following...Ch. 8 - Prob. 8.3PCh. 8 - Prob. 8.4PCh. 8 - Problem 8.5 Label each pair of alkenes as...Ch. 8 - Problem 8.6 Which alkene in each pair is more...Ch. 8 - Problem 8.7 Several factors can affect alkene...Ch. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10P
Ch. 8 - Prob. 8.11PCh. 8 - Problem 8.12 What alkenes are formed from each...Ch. 8 - Prob. 8.13PCh. 8 - Problem 8.14 What alkenes are formed from each...Ch. 8 - Problem 8.15 How does each of the following...Ch. 8 - Problem 8.16 Draw both the SN1 and E1 products of...Ch. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Problem 8.19 Explain why...Ch. 8 - Prob. 8.20PCh. 8 - Problem 8.21 Draw the alkynes formed when each...Ch. 8 - Problem 8.22 Draw the products in each...Ch. 8 - Problem 8.23 Draw a stepwise mechanism for the...Ch. 8 - 8.24 Rank the alkenes shown in the ball-and-stick...Ch. 8 - Prob. 8.25PCh. 8 - 8.26 What is the major E2 elimination product...Ch. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Prob. 8.29PCh. 8 - 8.30 Label each pair of alkenes as constitutional...Ch. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - For each of the following alkenes, draw the...Ch. 8 - Prob. 8.35PCh. 8 - Prob. 8.36PCh. 8 - Prob. 8.37PCh. 8 - What alkene is the major product formed from each...Ch. 8 - Prob. 8.39PCh. 8 - Prob. 8.40PCh. 8 - Pick the reactant or solvent in each part that...Ch. 8 - 8.42 In the dehydrohalogenation of...Ch. 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 - What alkyl chloride affords the following alkene...Ch. 8 - Draw the products formed when each dihalide is...Ch. 8 - Draw the structure of a dihalide that could be...Ch. 8 - Under certain reaction conditions, 2,...Ch. 8 - For which reaction mechanisms, SN1, SN2, E1 or...Ch. 8 - Draw the organic products formed in each...Ch. 8 - Prob. 8.55PCh. 8 - Draw all products, including stereoisomers, in...Ch. 8 - Draw all of the substitution and elimination...Ch. 8 - Prob. 8.58PCh. 8 - 8.59 Draw a stepwise, detailed mechanism for each...Ch. 8 - Draw the major product formed when...Ch. 8 - Draw a stepwise, detailed mechanism for the...Ch. 8 - Explain why the reaction of with gives ...Ch. 8 - Draw a stepwise detailed mechanism that...Ch. 8 - Prob. 8.64PCh. 8 - 8.65 Explain the selectivity observed in the...Ch. 8 - Prob. 8.66PCh. 8 - Prob. 8.67PCh. 8 - 8.68 (a) Draw all products formed by treatment of...
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- DRAW a stepwise reaction mechanism for this reaction. NO₂ -N3 C c 03, NaHCO3, CH2C12/MeOH. then Ac20, Et3N NO₂arrow_forward5. Which bromocyclohexane starting material would react faster - the cis or trans, and explain why? Draw both chair forms of the starting material to prove your point. Br K* OC(CH) K* OC(CH); Br cis transarrow_forwardDraw a stepwise mechanism for the attached reaction that illustrateshow two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reactionconditions, even though it is a 1 ° alkyl halide.arrow_forward
- Draw the product formed from cyclohex-2-enone in each of three reactions. Reaction 1 Reaction 2 Reaction 1 1. NaCN 1. (CH3)2CULI Reaction 2 product product 2. H30*, H2O 2. CH3CH2I 1. EtO,CCH2CO½ET NaOEt, HOET 2. Hао", Н-о, д Reaction 3 Reaction 3 productarrow_forwardcis- or trans-1-bromo-3-tert-butylcyclohexane will react faster in an E2 Which stereoisomer elimination reaction? Select the single best answer. trans- cis-arrow_forward16. Draw in the curved arrows for the SN2 reaction shown. CI s 17. Draw in the curved arrows for the E2 reaction shown. (CH3)3COK (CH3)3COH Oll ·xarrow_forward
- Which reacts faster in an E2 reaction: 3-bromocyclohexene or romocyclohexane? a. Which reacts faster in an E1 reaction?arrow_forwardShow how each alkene can be synthesized by a Wittig reactionarrow_forwardDraw the product of each thermal electrocyclic ring closure. CH3 b. CH3O2C CO,CH3 a. CH2 (2E,4Z,6Z)-2,4,6-0ctatrienearrow_forward
- Draw both the SN1 and E1 products of each reaction. CH3 a. -Br + H₂O CH3 b. CH3-C-CH₂CH₂CH3 CI + CH3CH₂OHarrow_forwardWhich E2 reaction in each pair is faster?arrow_forwardExplainwhythefollowingdeuterated1-bromo-2-methylcyclohexaneundergoes dehydrohalogenation by the E2 mechanism, to give only the indicated product. Two other alkenes are not observed.arrow_forward
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