Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 7.7, Problem 8P
Interpretation Introduction
Interpretation:
The name and stability (most stable to least stable) of given
Concept Introduction:
Delocalized electrons: Electrons that are not localized in one particular atom or bond and shared by three or more atoms are called delocalized electrons.
Compounds with two double bonds are known as dienes.
Stability of diene: The number of alkyl group increases with increasing the stability of the dienes.
Conjugated diene: Dienes are hydrocarbons with two double bonds; where the conjugated double bonds are separated by one single bond.
Resonance contributor: In some chemical compounds like benzene pi electrons are delocalized in it and difficult to locate it. Resonance contributor gives an idea of whereabouts of pi electrons. The exact structure with localized electrons are called resonance contributor.
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Name the following dienes and rank them from most stable to least stable. (Hint: Alkyl groups stabilize dienes in the same way they stabilize alkenes
Show that the [4 + 4] cycloaddition of two butadiene molecules to give cycloocta1,5-diene is thermally forbidden but photochemically allowed
1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far:
(a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results.
(b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.
Chapter 7 Solutions
Essential Organic Chemistry, Global Edition
Ch. 7.4 - Prob. 1PCh. 7.5 - Prob. 3PCh. 7.6 - a. Predict the relative bond lengths of the three...Ch. 7.6 - Prob. 5PCh. 7.6 - Prob. 6PCh. 7.7 - Prob. 7PCh. 7.7 - Prob. 8PCh. 7.7 - Prob. 9PCh. 7.7 - Prob. 10PCh. 7.8 - Which member of each pair is the stronger acid? a....
Ch. 7.8 - Which member of each pair is the stronger base? a....Ch. 7.9 - Prob. 13PCh. 7.9 - Which species in each of the following pairs is...Ch. 7.9 - Prob. 16PCh. 7.11 - Prob. 18PCh. 7.11 - Prob. 19PCh. 7.11 - Prob. 20PCh. 7.11 - Prob. 21PCh. 7.11 - Prob. 22PCh. 7.12 - Prob. 23PCh. 7.12 - Prob. 24PCh. 7.15 - Prob. 25PCh. 7.15 - Which of the following are aromatic? A...Ch. 7.17 - Prob. 29PCh. 7.17 - Prob. 30PCh. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Which of the compounds in each of the following...Ch. 7 - Prob. 39PCh. 7 - Prob. 40PCh. 7 - Prob. 41PCh. 7 - Prob. 42PCh. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Which species in each of the pairs in Problem 45...Ch. 7 - Rank the following anions in order from most basic...Ch. 7 - a. Which oxygen atom has the greater electron...Ch. 7 - Prob. 49PCh. 7 - Which compound is the strongest base?Ch. 7 - Prob. 51PCh. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Prob. 55PCh. 7 - a. Which dienophile in each pair is more reactive...Ch. 7 - Prob. 57PCh. 7 - Draw the product of each of the following...Ch. 7 - Prob. 59PCh. 7 - Prob. 60PCh. 7 - Prob. 61PCh. 7 - a. In what direction is the dipole moment in...Ch. 7 - Propose a mechanism for each of the following...Ch. 7 - Prob. 1PCh. 7 - Prob. 2PCh. 7 - Prob. 3PCh. 7 - Prob. 4PCh. 7 - Prob. 5PCh. 7 - Prob. 6PCh. 7 - Prob. 7PCh. 7 - Prob. 8PCh. 7 - Prob. 9PCh. 7 - Prob. 10PCh. 7 - Prob. 11PCh. 7 - Prob. 12P
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- The central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other.(a) Draw an orbital diagram of allene, showing why the two ends are perpendicular.(b) Draw the two enantiomers of penta-2,3-diene. A model may be helpfularrow_forwarda. Show that [4+4] cycloaddition of two butadiene molecules to give cycloocta-1,5-diene is thermally forbidden but photochemically allowed b.Thermally allowed cycloaddition of the two butadiene molecules when there's a different. Show reaction and explain why it is thermally allowarrow_forwardExplain the Carbocation Rearrangements ?arrow_forward
- This is a Diels-Alder reaction between ethylene and cis-1,3-butadiene. For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.arrow_forwardHow many linear dienes have molecular formula C6H10? (Disregard cis–trans isomers.) A. How many of the linear dienes in part a are conjugated dienes? B. How many are isolated dienes? C. How many are cumulated dienes?arrow_forwardWhat is the best way to draw a molecular orbital diagram for 1,3-cyclopentadiene, identifying the Lowest unoccupied molecular orbital and the highest occupied molecular orbital?arrow_forward
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