7. Consider the C=O stretching data for the following cyclic ketones: cyclopropane 1813 cm¹; cyclobutanone 1791 cm³¹; cyclopentanone 1740 cm³¹. (a) which ketone has the strongest bond? (b) where in the trend would you expect the C-O stretch of cyclopropenone? (Use the hybridization information in the same way we used hybridization for C-H stretching.)

7. Consider the C=O stretching data for the following cyclic ketones: cyclopropane 1813 cm¹; cyclobutanone 1791 cm³¹; cyclopentanone 1740 cm³¹. (a) which ketone has the strongest bond? (b) where in the trend would you expect the C-O stretch of cyclopropenone? (Use the hybridization information in the same way we used hybridization for C-H stretching.)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter15: Benzene And Aromaticity

Section15.SE: Something Extra

Problem 17VC: Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon (Î¼ = 1.0...

See similar textbooks

Similar questions

Draw the structure of the two tertiary (3°) amines with molecular formula C6H15N that contain a group with 3 carbon atoms in the largest group. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.
The unsaturation number or degree of unsaturation (U) can be used to determine the number of rings and multiple bonds in a compound from its molecular formula. Given a structure, you can determine the number of hydrogens without having to count them explicitly. Consider three compounds and their degree of unsaturation. (a) A compound A has the molecular formula C7H13ClN2OC7⁢H13⁢ClN2O. How many rings and/or π bonds does it contain?
The degree of unsaturation, or index of hydrogen deficiency, is the number of pi bonds plus rings in a molecule. Specify the degree of unsaturation (index of hydrogen deficiency) of the following formulas: (a) C9H12 (b) C,H40| (c) C,H,N2
Draw the structures of the four primary (1°) amines with molecular formula C5H13N that contain a chain with 4 carbon atoms in the longest continuous carbon chain. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.
2. The full structural formulae of three organic compounds, P, Q and R, are shown below. H H H H HH HHHH Н-С -с- Н H-C- C - C = C – H H - C - C = C – C – H H H H H Q P (a) State one similarity between P, Q and R in terms of their molecular formulae. (b) Name the homologous series that compounds P, Q and R belong to. (c) State one similarity between Q and R in terms of chemical bonding id) Which of these compounds are isomers? Explain your answer.
• -- H (b) H,C 3-methylhexane CH, (c) B கூ CH, CH, HgCG; சீகூ H₂CH H 3-ethyl-1-methyloctane 3,3 diethyl pentane 5Å, Å,CH, W CH3 CH2 CH₂ W21 Su2... CH3 X -CH3 G b F E L c
For each pair of compounds, predict the one with a higher boiling point. Which compoundshave zero dipole moments?(a) cis-1,2-dichloroethene or cis-1,2-dibromoethene
(a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?
For which of the following molecules are there two unique configurations about the double bond? Explain. (a) (CH3)2C=CHCI; (b) H2C=CHCH,CH3; (c) CIHC=CHBr; (d) HC=CCH=CHCI
Draw the structure of the one tertiary (3°) amine with molecular formula C5H13N that does not contain a 3-carbon chain. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms
The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy
The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpairedelectron onto three carbon atoms.(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atomsshare the positive charge? Does this picture agree with the resonance picture?(h) Add an…