Identify the structural explanations for the relative rates of reactivity for compounds 5, 6, and 7. effects. The cyano group than the acetoxy (OAc) group in compound 4. The substituents in compounds 5, 6 and 7 affect the alkene reactivity primarily by (CN) group in 6 must be a stronger Steric effects are likely a contributing factor in compound Identify the correct structural explanation for the relative rates of reactivity for compounds 2, 8, and 9. O Compounds 8 and 9 are disubstituted alkenes. The lowest relative reactivity is due to increased steric effects. O Compound 2 is the only mono-substituted alkene with no significant electronic effects. O In compound 9, the electron-withdrawing effect of the chlorine atom is superimposed upon the increased steric effect which further lowers the reactivity. O All the above.

Chemistry
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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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9-Borabicyclo[3.3.1)nonane (9-88N) is a reagent commonly used in the hydroboration of alkynes (section 9.7), but it can also be
employed in reactions with alkenes. The following table provides the relative rates of hydroboration (using 9-BBN) for a variety of
alkenes (J. Am. Chem. Soc. 1989, 111, 1414-1418):
Alkenes
Relative Reactivity
CH₂=CHOBU, 1
CH2=CHBu, 2
CH2=CHCH₂OME, 3
CH2=CHOAC, 4
CH₂=CHCH₂OAC, 5
CH2=CHCH2CN, 6
CH2=CHCH2CL, 7
cis-2-Butene, 8
trans-CH3CH2CH=CHCI, 9
so an electron-rich
that makes the alkene
and 5 have inductively
nucleophile
1615
more
100
32.5
22.8
21.9
5.9
4.0
Identify the structural explanations for the relative rates of reactivity for compounds 1 to 5.
eTextbook and Media
0.95
0.003
Hydroboration involves the reaction of an electrophilic
boron reagent with a nucleophilic
alkene,
alkene will react faster. The butaxy group on compound 1 has resonance with the pi bond
electron-rich, making it more reactive. Compared to compound 2, compounds 3,4
groups that make the alkene less reactive because it is a weaker
electron-withdrawing
Identify the structural explanations for the relative rates of reactivity for compounds 5, 6, and 7.
effects. The cyano
group than the acetaxy (OAc) group in compound 4.
The substituents in compounds 5, 6 and 7 affect the alkene reactivity primarily by
(CN) group in 6 must be a stronger
Steric effects are likely a contributing factor in compound
Identify the correct structural explanation for the relative rates of reactivity for compounds 2, 8, and 9.
O Compounds 8 and 9 are disubstituted alkenes. The lowest relative reactivity is due to increased steric effects.
O Compound 2 is the only mono-substituted alkene with no significant electronic effects.
O In compound 9, the electron-withdrawing effect of the chlorine atom is superimposed upon the increased steric
effect which further lowers the reactivity.
O All the above.
Transcribed Image Text:9-Borabicyclo[3.3.1)nonane (9-88N) is a reagent commonly used in the hydroboration of alkynes (section 9.7), but it can also be employed in reactions with alkenes. The following table provides the relative rates of hydroboration (using 9-BBN) for a variety of alkenes (J. Am. Chem. Soc. 1989, 111, 1414-1418): Alkenes Relative Reactivity CH₂=CHOBU, 1 CH2=CHBu, 2 CH2=CHCH₂OME, 3 CH2=CHOAC, 4 CH₂=CHCH₂OAC, 5 CH2=CHCH2CN, 6 CH2=CHCH2CL, 7 cis-2-Butene, 8 trans-CH3CH2CH=CHCI, 9 so an electron-rich that makes the alkene and 5 have inductively nucleophile 1615 more 100 32.5 22.8 21.9 5.9 4.0 Identify the structural explanations for the relative rates of reactivity for compounds 1 to 5. eTextbook and Media 0.95 0.003 Hydroboration involves the reaction of an electrophilic boron reagent with a nucleophilic alkene, alkene will react faster. The butaxy group on compound 1 has resonance with the pi bond electron-rich, making it more reactive. Compared to compound 2, compounds 3,4 groups that make the alkene less reactive because it is a weaker electron-withdrawing Identify the structural explanations for the relative rates of reactivity for compounds 5, 6, and 7. effects. The cyano group than the acetaxy (OAc) group in compound 4. The substituents in compounds 5, 6 and 7 affect the alkene reactivity primarily by (CN) group in 6 must be a stronger Steric effects are likely a contributing factor in compound Identify the correct structural explanation for the relative rates of reactivity for compounds 2, 8, and 9. O Compounds 8 and 9 are disubstituted alkenes. The lowest relative reactivity is due to increased steric effects. O Compound 2 is the only mono-substituted alkene with no significant electronic effects. O In compound 9, the electron-withdrawing effect of the chlorine atom is superimposed upon the increased steric effect which further lowers the reactivity. O All the above.
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