ochem chapter 10 homework, Assignments of Organic Chemistry

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Chem 0310 Organic Chemistry 1 HW Problem Sets
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Chapter 10 HW Problem Set
Assigned Chapter 10 Textbook Problems (very important for problem practice):
7th edition: 33-37, 38a, 39
8th edition: 34-38, 39a, 40
Use all the assigned textbook problems above for practice. On this HW, show your work for five
individual problems that you consider representative from the assigned textbook problems. (e.g.
36b counts as one problem). Insert a blank page if more space is needed.
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Chapter 10 HW Problem Set Assigned Chapter 10 Textbook Problems (very important for problem practice): 7th edition: 33 - 37, 38a, 39 8th edition: 34 - 38, 39a, 40 Use all the assigned textbook problems above for practice. On this HW, show your work for five individual problems that you consider representative from the assigned textbook problems. (e.g. 36 b counts as one problem). Insert a blank page if more space is needed.

Complete the following problems: Q1 : Order the following compounds from most upfield to most downfield: Q 2 : For the compounds below, a) Predict how many distinct H peaks would be observed on 1 H NMR. b) Predict the splitting pattern of each distinct H peak. c) Predict how many distinct C peaks would be observed on 1 H-decoupled 13 C NMR. Q3 : An unlabeled sample has the 13 C NMR data: δ 219.6, 38.0, 23.1 ppm. Circle the structure that best fits the data: O N O Br Br O Br Br O Cl Cl O N O OH NH 2 OH O O H O

f) C 6 H 14 g) C 4 H 8 Cl 2

δ = 1.5 (d, 6 H)

δ = 4.1 (q, 2 H)

h) C 4 H 8 Cl 2

δ = 1.6 (d, 3 H)

δ = 2.1 (q, 2 H)

δ = 3.6 (t, 2 H)

δ = 4.2 (sex, 1 H)

i) C 4 H 8 Cl 2

δ = 1.0 (t, 3 H)

δ = 1.9 (quin, 2 H)

δ = 3.6 (d, 2 H)

δ = 3.9 (quin, 1 H)

j) C 5 H 10 O

δ = 9.8 (s, 1 H)

δ = 1.1 (s, 9 H)

k) C 6 H 12 O

1 H NMR: δ = 0.90 (t, 6 H)

δ = 1.53 (m, 4 H) δ = 2.34 (m, 1 H) δ = 9.72 (d, 1 H)

l) C 6 H 10 O 4

(^13) C NMR: δ 13.5, δ 41.2, δ 177. (^1) H NMR: δ 1.13 (6 H, d, J = 7 Hz) δ 2.65 (2 H, quartet, J = 7 Hz) δ 9.9 (2 H, broad s, disappears after D 2 O shake)