Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 7, Problem 7.59SP
E1 eliminations of
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What explains why many aldehydes and ketones can undergo self- condensation reactions in basic conditions?
The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon a an electrophile
O The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile
O The oxygen of the carbonyl group can attack the carbon of the carbonyl group
Only esters can undergo self-condensation reactions
Explain why pentane-2,4-dione forms two different alkylation products (Aor B) when the number of equivalents of base is increased from one totwo.
2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but
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of negative charge needed to be a good nucleophile.
CH3CH₂O
CH3CO₂
CH3SO3
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CH₂OH
Chapter 7 Solutions
Organic Chemistry (9th Edition)
Ch. 7.3A - Prob. 7.1PCh. 7.3A - Prob. 7.2PCh. 7.3B - Draw five more compounds of formula C4H6NOC1.Ch. 7.3B - For each of the following molecular formulas,...Ch. 7.4 - Give the systematic (IUPAC) names of the following...Ch. 7.5B - The following names are all incorrect. Draw the...Ch. 7.5B - Prob. 7.8PCh. 7.5B - a. How many stereogcmc double bonds are in...Ch. 7.6 - Teflon-coated frying pans routinely endure...Ch. 7.7B - Prob. 7.11P
Ch. 7.8B - Use the data in Table7-2 to predict the energy...Ch. 7.8C - Prob. 7.13PCh. 7.8E - Explain why each of the following alkenes is...Ch. 7.8F - Prob. 7.15PCh. 7.10 - Prob. 7.16PCh. 7.10A - SN1 substitution and E1 elimination frequently...Ch. 7.10C - Prob. 7.18PCh. 7.10C - Prob. 7.19PCh. 7.10C - Prob. 7.20PCh. 7.11 - Prob. 7.21PCh. 7.11 - Prob. 7.22PCh. 7.12 - Prob. 7.23PCh. 7.12 - Prob. 7.24PCh. 7.13 - Prob. 7.25PCh. 7.14B - Prob. 7.26PCh. 7.14B - Make models of the blowing compounds, and predict...Ch. 7.15 - Prob. 7.28PCh. 7.15 - Prob. 7.29PCh. 7.15 - Prob. 7.30PCh. 7.15 - Prob. 7.31PCh. 7.16 - Predict the major and minor elimination products...Ch. 7.17B - Predict the products and mechanisms of the...Ch. 7.18 - Propose mechanisms for the following reactions.Ch. 7.18 - Prob. 7.35PCh. 7.19B - The dehydrogenation of butane to trans-but-2-ene...Ch. 7.19B - Prob. 7.37PCh. 7.19B - Prob. 7.38PCh. 7.19B - Prob. 7.39PCh. 7 - Prob. 7.40SPCh. 7 - Prob. 7.41SPCh. 7 - Prob. 7.42SPCh. 7 - Prob. 7.43SPCh. 7 - Prob. 7.44SPCh. 7 - Prob. 7.45SPCh. 7 - Prob. 7.46SPCh. 7 - The energy difference between cis- and...Ch. 7 - Prob. 7.48SPCh. 7 - Prob. 7.49SPCh. 7 - Prob. 7.50SPCh. 7 - What halides would undergo E2 dehydrohalogenation...Ch. 7 - Prob. 7.52SPCh. 7 - Prob. 7.53SPCh. 7 - Write a balanced equation for each reaction,...Ch. 7 - Prob. 7.55SPCh. 7 - Using cyclohexane as your starting material, show...Ch. 7 - Show how you would prepare cyclopentene from each...Ch. 7 - Prob. 7.58SPCh. 7 - E1 eliminations of alkyl halides are rarely useful...Ch. 7 - Prob. 7.60SPCh. 7 - Propose mechanisms for the following reactions....Ch. 7 - Prob. 7.62SPCh. 7 - Prob. 7.63SPCh. 7 - Prob. 7.64SPCh. 7 - Prob. 7.65SPCh. 7 - Prob. 7.66SPCh. 7 - Prob. 7.67SPCh. 7 - Prob. 7.68SPCh. 7 - Prob. 7.69SPCh. 7 - Explain the dramatic difference in rotational...Ch. 7 - One of the following dichloronorbornanes undergoes...Ch. 7 - A graduate student wanted to make...Ch. 7 - Prob. 7.73SPCh. 7 - Prob. 7.74SPCh. 7 - Prob. 7.75SPCh. 7 - Prob. 7.76SP
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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
- In the substitution reaction of 2-chloro-2,4- dimethylpentane with water, the rate at which the alcohol product is formed depends on the concentration of the nucleophile. Select one: True Falsearrow_forwardGive one example of elimination reaction (E2) type. Show the reactants materials and the product. Draw the reaction mechanism?arrow_forwardThe reaction of an amine with an alkyl halide gives an ammonium salt. The rate of this SN2 reaction is sensitive to the polarity of the solvent. Draw an energy diagram for this reaction in a nonpolar solvent and another in a polar solvent. Consider the nature of the transition state, and explain why this reaction should be sensitive to the polarity of the solvent. Predict whether it will be faster or slower in a more polar solvent.arrow_forward
- Decide which compounds from the list below are best suited for nucleophilic addition reactions and which ones are more appropriate for nucleophilic substitution reactions.arrow_forwardIn 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.arrow_forwardPredict whether the following nucleophiles are excellent nucleophiles, good nucleophiles, or poor nucleophiles based on their structure, and sort them accordingly.arrow_forward
- Nucleophilic carbon atoms are often important in the formation of carbon–carbon bonds. Carbon atoms are not good nucleophiles if they do not possess a lone pair of electrons.arrow_forwardWhat is the product and mechanism for this reaction?arrow_forwardExplain why pentane-2,4-dione forms two different alkylation products (A or B) when the number of equivalents of base is increased from one to two.arrow_forward
- In the presence of heat or light, diazomethane is converted into a carbene that adds to alkenes. Draw the correct products for the following reaction.arrow_forwardExplain why pentane-2,4-dione forms two alkylation products (A and B) when the number ofequivalents of base is increased from one to two.arrow_forwardDraw the neutral organic starting material. The Hint: The reaction conditions support electrophilic addition of Br2 to an alkene's C=C double bond, which would normally yield a dibromo product. However, the product has only one bromine atom, with a C–O bond on the adjacent carbon. This fragment is diagnostic for a halohydrin, where an oxygen nucleophile (water or alcohol) reacts with a bromonium intermediate to generate the O–CH2CH2–Br motif. Work backwards to determine what the starting material must look like. There should be an alcohol and an alkene in the neutral organic starting material.arrow_forward
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