ORGANIC CHEMISTRY LSLF W/CONNECT >BI<
5th Edition
ISBN: 9781260293609
Author: SMITH
Publisher: MCG CUSTOM
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Chapter 8, Problem 8.35P
Interpretation Introduction
(a)
Interpretation: The by-products of the given reaction are to be drawn and the movement of electrons is to be shown by using curved arrow notation.
Concept introduction: In E2 elimination reactions, the proton is abstracted from the beta carbon to form an
Interpretation Introduction
(b)
Interpretation: The effect of the given change on the
Concept introduction: In E2 elimination reactions, substituents which are adjacent to each other are eliminated from an alkyl halide to form an alkene. A concerted mechanism is followed for this type of reactions.
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Consider the attached E2 reaction
What happens to the reaction rate with each of the following changes?[1] The solvent is changed to DMF.
[2] The concentration of −OC(CH3)3 is decreased.
[3] The base is changed to −OH.
[4] The halide is changed to CH3CH2CH2CH2CH(Br)CH3.
[5] The leaving group is changed to I−.
How does changing the base from −OH to H2O affect the rate of an E2 reaction?
Consider the following SN2 reaction.a.Draw a mechanism using curved arrows.
b. Draw an energy diagram. Label the axes, the reactants, products, Ea, and ΔH°. Assume that the reaction is exothermic.
c. Draw the structure of the transition state.
d.What is the rate equation?
e.What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from Br− to I−; [2] The solvent is changed from acetone to CH3CH2OH; [3] The alkyl halide is changed from CH3(CH2)4Br to CH3CH2CH2CH(Br)CH3; [4] The concentration of −CN is increased by a factor of five; and [5] The concentrations of both the alkyl halide and −CN are increased by a factor of five.
Chapter 8 Solutions
ORGANIC CHEMISTRY LSLF W/CONNECT >BI<
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 1. What type of reaction is occuring in step 3? (halogenation, hydrohalogenation, reduction, keto–enol tautomerism, dehydrohalogenation, acid-catalyzed hydration, base-catalyzed hydration) 2. Which reagent is necessary for step 3? (Br2, HBr, H2/Pt, NaNH2, H20/H2SO4/HgSO4)arrow_forwardRank the following E2 reactions in order of their increasing rate:arrow_forwarda. Indicate how each of the following factors affects an E1 reaction: 1. the strength of the base 2. the concentration of the base 3. the solvent b. Indicate how each of the same factors affects an E2 reaction.arrow_forward
- Rank the following in order of reactivity in an E1 reaction, (1 = most reactive in an E1 reaction; 3 = least reactive in an E1 reaction).arrow_forwardQ4 Which statement below about Sn1 reactions is incorrect? (A) SN1 reactions are stepwise and have intermediates. (B) The slow step in a SN1 reaction is formation of the carbocation intermediate. (C) SN1 reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a SN1 reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Sn1 reactions as they tend to help stabilize carbocation intermediates.arrow_forwardConsider 3-iodo-2,3-dimethylpentane and 3-iodo-2methylpentane. a. which reacts faster in an Sn2 reaction? Explain. b. which reacts faster in an E2 reaction? Explain.arrow_forward
- Consider the following SN1 reaction.a.Draw a mechanism for this reaction using curved arrows. b.Draw an energy diagram. Label the axes, starting material, product, Ea, and ΔH°. Assume that the starting material and product are equal in energy. c.Draw the structure of any transition states. d.What is the rate equation for this reaction? e. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from I− to Cl−; [2] The solvent is changed from H2O to DMF; [3] The alkyl halide is changed from (CH3)2C(I)CH2CH3 to (CH3)2CHCH(I)CH3; and [4] The concentrations of both the alkyl halide and H2O are increased by a factor of five.arrow_forwardWhich mechanism gave the main product in the reaction shown in Figure 8? * A- SN1 B- SN2 C- E1 D- E2arrow_forwardRank the nucleophiles in each group in order of increasing nucleophilicity. a.−OH, −NH2, H2O b.−OH, Br−, F− (polar aprotic solvent) c.H2O, −OH, CH3CO2−arrow_forward
- How does the rate of an SN2 reaction change as the alkyl group in the substrate alkyl halide changes from CH3 1° 2° 3°?arrow_forwardDraw the reaction mechanism of the E2 reaction between 2-chloro-2-methylpentane with potasium hydroxide, KOHarrow_forwardWhich of the following is not true of the E2 reaction? A bulky base such as tert-butoxide will favor the Hofmann product. concerted mechanism no reactive intermediate Rate = k [R-X] alkyl halide preference: 3o > 2o > 1oarrow_forward
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