Exam 2

Question 1

Predict the product of the following preparation of alcohol reactions:

Answer 1

Question 2

Predict the product of the following preparation of alcohol reactions:

Answer 2

Question 3

Predict the product of the following preparation of alcohol reactions:

Answer 3

Question 4

Predict the product of the following preparation of alcohol reactions:

Answer 4

Question 5

Predict the product of the following preparation of alcohol reactions:

Answer 5

Question 6

Predict the product of the following preparation of alcohol reactions:

Answer 6

Question 7

Predict the product of the following preparation of alcohol reactions:

Answer 7

Question 8

Predict the following alcohol substitution reactions. Remember to indicate stereochemistry.

Answer 8

Question 9

Predict the following alcohol substitution reactions. Remember to indicate stereochemistry.

Answer 9

Question 10

Predict the following alcohol substitution reactions. Remember to indicate stereochemistry.

Answer 10

Question 11

Predict the following alcohol substitution reactions. Remember to indicate stereochemistry.

Answer 11

Question 12

Predict the following alcohol substitution reactions. Remember to indicate stereochemistry.

Answer 12

Question 13

Predict the following alcohol substitution reactions. Remember to indicate stereochemistry.

Answer 13

Question 14

The compound below has 4 different nitrogens. (a) Identify their hybridization, and (b) rank them in terms of their basicity. (1 = most basic…4 = least basic)

Answer 14

Question 15

The compound below has 4 different nitrogens. (a) Identify their hybridization, and (b) rank them in terms of their basicity. (1 = most basic…4 = least basic)

Answer 15

Question 16

Even though there are technically four things attached to the amine drawn below, why is it impossible to isolate this structure? In other words, why are amines not chiral?

Answer 16

Question 17

In the following pairs of alcohols, identify the alcohol with the lower pKa. For full credit, provide a rational and draw the conjugate base that justifies your answer.

Answer 17

Question 18

In the following pairs of alcohols, identify the alcohol with the lower pKa. For full credit, provide a rational and draw the conjugate base that justifies your

Answer 18

Question 19

Please explain the origin of regioselectivity in the following reaction:

Answer 19

Question 20

Nomenclature. Please provide the IUPAC nomenclature for the following compounds. The common name will also be accepted if it applies.

Answer 20

triethyl amine (TEA)

Question 21

Nomenclature. Please provide the IUPAC nomenclature for the following compounds. The common name will also be accepted if it applies.

Answer 21

(1R,4S)-4-aminocyclohex-2-en-1-ol

Question 22

Nomenclature. Please provide the IUPAC nomenclature for the following compounds. The common name will also be accepted if it applies.

Answer 22

2-phenyl-1-ethanol

Question 23

Nomenclature. Please provide the IUPAC nomenclature for the following compounds. The common name will also be accepted if it applies.

Answer 23

N-ethyl-3-methyl-1-cyclopentanamine

Question 24

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Question 25

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Question 26

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Question 27

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Question 28

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Question 29

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Question 30

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Question 31

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Question 32

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Question 33

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Question 34

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Question 35

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Question 36

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Question 37

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Question 38

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Question 39

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Question 40

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Question 41

Identify the alcohol with a lower pKa

Answer 41

Question 42

Identify the alcohol with a lower pKa

Answer 42

Question 43

Is this reaction oxidation or reduction?

Answer 43

oxidation

Question 44

Is this reaction oxidation or reduction?

Answer 44

reduction

Question 45

Answer 45

Question 46

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Question 47

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Question 48

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Question 49

Provide a reasonable synthesis for this grignard

Answer 49

Question 50

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Question 51

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Question 52

Write the mechanism

Answer 52

Question 53

Write the mechanism

Answer 53

Question 54

Draw structure

Answer 54

Question 55

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Question 56

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Question 57

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Question 58

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Question 59

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Question 60

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Question 61

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Question 62

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Question 63

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Question 64

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Question 65

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Question 66

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Question 67

Answer 67