Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Question
Chapter 16, Problem 16.40P
Interpretation Introduction
Interpretation: The given diene is to be ranked in increasing order of heat of hydrogenation.
Concept introduction: Diene is a hydrocarbon that contains two
Conjugated diene consists of two double bonds that are separated by a single bond, whereas isolated diene also consists of two double bond but they are separated by two more carbon atoms.
The example that shows the basic difference between conjugated diene and isolated diene is shown below.
Figure 1
The stability of conjugated diene is more than isolated diene. Due to which the heat of hydrogenation is smaller for conjugated diene, whereas heat of hydrogenation for isolated diene is larger.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction.
Rank the following radicals in order of increasing stability.
Furan and maleimide undergo a Diels–Alder reaction at 25 °C to give the endo isomer of the product. When the reactiontakes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of theproduct isomerizes to the exo isomer at 90 °C.furan: O maleimide:OON H(a) Draw and label the endo and exo isomers of the Diels–Alder adduct of furan and maleimide.(b) Which isomer of the product would you usually expect from this reaction? Explain why this isomer is usually favored.(c) Examine your answer to (b) and determine whether this answer applies to a reaction that is kinetically controlled orone that is thermodynamically controlled, or both.(d) Explain why the endo isomer predominates when the reaction takes place at 25 °C and why the exo isomer predominates at 90 °C
Chapter 16 Solutions
Organic Chemistry
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Problem 16.3 Draw a second resonance structure for...Ch. 16 - Prob. 16.4PCh. 16 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - Problem 16.9 Determine the hybridization of the...Ch. 16 - Problem 16.10 Draw the structure consistent with...
Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.16 Draw the products formed when each...Ch. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.18PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Problem 16.22 Rank the following dienophiles in...Ch. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Problem 16.25 What diene and dienophile are needed...Ch. 16 - Prob. 16.26PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.28PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.30PCh. 16 - 16.31 Which of the following systems are...Ch. 16 - 16.32 Draw all reasonable resonance structures for...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Prob. 16.36PCh. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Prob. 16.38PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.40PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.42PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.45PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.54PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.56PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Prob. 16.58PCh. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Prob. 16.67PCh. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74PCh. 16 - Prob. 16.75P
Knowledge Booster
Similar questions
- Cyclopentadiene is unusually acidic for a hydrocarbon. Which of the following explains why that is? The carbon atoms of cyclopentadiene are all sp hybridized. A В Cyclopentadiene is aromatic. Removal of a proton from cyclopentadiene yields an C aromatic anion. Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical. D Removal of a hydride ion from cyclopentadiene produces an E aromatic cation. H H. cyclopentadienearrow_forwardWhat combination of diene and dienophile undergoes Diels-Alder reaction to give adduct?arrow_forwardThe following diene does not undergo a Diels-Alder reaction with maleic anhydride, both in thermal and photochemical conditions. Explain why this reaction does not occur.arrow_forward
- Which of the following would be the best diene for a Diels - Alder cycloaddition reaction? A B C D Which of the following would be the best diene for a Diels-Alder cycloaddition reaction? A G A B C D B Uarrow_forwardWhich of the following conformations would undergo Diels-Alder reaction? D. C. B. A.arrow_forwardWhat diene and dienophile are needed to prepare each compound by a Diels–Alder reaction?arrow_forward
- There is TWO Blanks, what should I put in them?arrow_forward1. Show the Diels-Alder product from the reaction shown ..... A в Earrow_forwardWould you expect nitroethylene to be more or less reactive than ethylene in a Diels-Alder reaction? (Hint: Draw the resonance structures of nitroethylene.) Ethylene neither do Nitroethylene O Ethylene is more reactive than nitroethylene in Diels-Alder reaction O Nitroethylene is more reactive than ethylene in Diels-Alder reaction samearrow_forward
- Ll.35.arrow_forwardThe rate of a Diels-Alder reaction is favored by select all that apply electron withdrawing dienophile electron donating dienophile s-cis diene s-trans diene sdsdienophilearrow_forwardCompounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe O C8H12O2 R C8H12O2 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. Using curly arrows, draw the mechanism for the reaction of P and Q to form the dominant regioisomer you have predicted in your answer to part (ii) above.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you