Question

Acid-catalyzed dehydration of 4-methyl-2-pentanol gives the following five methylpentenes: OH H A B C C-C= D E Part 1: Do this part on a separate sheet. Using curved arrows to show the flow of electrons, show how each of the five methylpentenes could be formed under the reaction conditions. Be sure to show all proton transfers and rearrangements explicitly. Alkenes A, B, and C require no carbocation rearrangement, while D requires one and E requires two. Part II: Complete the following table. Name the five methylpentenes using IUPAC systematic nomenclature. For each of the five alkenes, determine the number of types of signals that would be present in the $^1$H and $^{13}$C NMR. Alkene IUPAC Name # of $^1$H Types # of $^{13}$C Types A (E)-4-methyl-2-pentene 4 5 B (Z)-4-methyl-2-pentene 4 5 C 4-methyl-1-pentene 4 5 D 2-methyl-2-pentene 4 5 E 2-methyl-1-pentene 5 6

          Acid-catalyzed dehydration of 4-methyl-2-pentanol gives the following five
methylpentenes:
OH
H
A
B
C
C-C=
D
E
Part 1: Do this part on a separate sheet. Using curved arrows to show the flow of
electrons, show how each of the five methylpentenes could be formed under the
reaction conditions. Be sure to show all proton transfers and rearrangements explicitly.
Alkenes A, B, and C require no carbocation rearrangement, while D requires one and E
requires two.
Part II: Complete the following table. Name the five methylpentenes using IUPAC
systematic nomenclature. For each of the five alkenes, determine the number of types
of signals that would be present in the $^1$H and $^{13}$C NMR.
Alkene
IUPAC Name
# of $^1$H Types
# of $^{13}$C Types
A (E)-4-methyl-2-pentene
4
5
B (Z)-4-methyl-2-pentene
4
5
C
4-methyl-1-pentene
4
5
D
2-methyl-2-pentene
4
5
E
2-methyl-1-pentene
5
6

Acid-catalyzed dehydration of 4-methyl-2-pentanol gives the following five
methylpentenes:
OH
H
A
B
C
C-C=
D
E
Part 1: Do this part on a separate sheet. Using curved arrows to show the flow of
electrons, show how each of the five methylpentenes could be formed under the
reaction conditions. Be sure to show all proton transfers and rearrangements explicitly.
Alkenes A, B, and C require no carbocation rearrangement, while D requires one and E
requires two.
Part II: Complete the following table. Name the five methylpentenes using IUPAC
systematic nomenclature. For each of the five alkenes, determine the number of types
of signals that would be present in the ^1H and ^13C NMR.
Alkene
IUPAC Name
# of ^1H Types
# of ^13C Types
A (E)-4-methyl-2-pentene
4
5
B (Z)-4-methyl-2-pentene
4
5
C
4-methyl-1-pentene
4
5
D
2-methyl-2-pentene
4
5
E
2-methyl-1-pentene
5
6

Added by Theresa O.

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