Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 6.16, Problem 6.27P
For each reaction, give the expected substitution product and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2).
- a. 2 – chloro – 2 – methylbutane + CH3COOH
- b. isobutylbromide + sodiummethoxide
- c. l – iodo – 1 – methylcyclohexane + ethanol
- d. cyclohexylbromide + methanol
- e. cyclohexylbromide + sodiumethoxide
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Below is the equation for a nucleophilic substitution reaction and some experimental data.
CH3CH2Br + CH3COO- ⇌ CH3CH2CO2CH3 + Br- ΔH=-75 kJ/mol
Rate = k [CH3CH2Br][CH3COO-]
Which reaction energy profile would be the best representative of the data provided?
For each reaction, give the expected solution product and predict whether the machanism will be first order (SN1) or second order (SN2) :
a) 2-chloro-2-methylbutane +CH3COOH
b) isobutyl bromide + NaOMe
c) 1-iodo-1-methylcyclohexane + CH3CH2OH
Choose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number.
HCl (aq), Zn(Hg)
KMnO4, H3O+
CH3Cl, AlCl3
HNO3, H2SO4
Cl2, FeCl3
fuming sulfuric acid
Chapter 6 Solutions
Organic Chemistry (9th Edition)
Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4PCh. 6.4 - Prob. 6.5PCh. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7PCh. 6.6B - Prob. 6.8PCh. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...
Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
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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
- For 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_forwardwhat structure show the transition state for the rate determining step in the sn1 reaction with this picture?arrow_forward20. (a) Show all steps in the synthesis of 2-pentene from 2-bromopentane. Show the structure of all reactants and product. CH3CHBrCH2CH2CH3 -------> CH3CH=CHCH2CH3 (b) Correctly identify the mechanism in (a) above(SN2, SN1, E2, E1)arrow_forward
- Give all the reagents, in order, that lead to forming the product.arrow_forwardShow the reaction mechanism for the formation of:a. RCONH2 from the reaction of RCOOR’ with NH3arrow_forwardThe product of reaction between acetone and bromine (excess) with KOH excess is A. Ch2BrCOCh3 B. ChBr3 C.ChBr2COCH3 D.CBr3COCH3 E.Ch2BrCOCHBr2arrow_forward
- 6. Identify the best reagent(s) for this reaction. (see attached screenshot). a. H2SO4, HgSO4, H2O b. 1. Disiamylborane, 2. HO–, H2O2 c. K2Cr2O7, H+ d. NaOCl e. H2, Pdarrow_forwardHow does changing the alkyl halide from CH3CH2Br to (CH3)2CHBr affect the rate of an E2 reaction?arrow_forwardWhich reacts faster in an E2 elimination, cis-or-trans1-bromo-3-tert-butylcyclohexanearrow_forward
- 6. For each of the following reactions: a) say what is the expected Mechanism sn1 or sn2 and say why. b) For some of the reactions say if the product is optically active and say why. c) For some of the rxns say if their kinetics are unimolecular (Uni) or bimolecular (Bi) and explain Mechanisarrow_forwardIn each reaction box, place the best reagent and conditions from the list below.arrow_forwardIdentify the reagents needed to come up with the given compounds. Pls Separate the reagents with a comma and a space. (ex. HNO3, H2SO4). For a multi-step reaction, separate the reagents with a semi-colon. (ex. HNO3, H2SO4; CH3Cl, AlCl3) There should be 9 reagentsarrow_forward
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