850 Exam 1 (pka and bond ionization)

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33 Terms

1
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<p>Carboxylic Acid pka?</p>

Carboxylic Acid pka?

pka is approximately 5

2
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<p>Phenol pka?</p>

Phenol pka?

pka is approximately 10

3
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<p>Vinyl Alcohol pka?</p>

Vinyl Alcohol pka?

pka is approximatly 10

4
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<p>1,3-diketone pka?</p>

1,3-diketone pka?

pka is approximately 10

5
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<p>Diamine pka?</p>

Diamine pka?

pka is approximately 10

6
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<p>Water pka?</p>

Water pka?

pka is approximately 14

7
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<p>Alcohol pka?</p>

Alcohol pka?

pka is approximately 15-18

Primary alcohols are most acidic then secondary then tertiary

8
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<p>Ketone pka?</p>

Ketone pka?

pka is approximately 20

9
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<p>Ester (carbon next to ketone) pka?</p>

Ester (carbon next to ketone) pka?

pka is approximately 25

10
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<p>Acetonitrile pka?</p>

Acetonitrile pka?

pka is approximately 25

11
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<p>Alkyne pka?</p>

Alkyne pka?

pka is approximately 25

12
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<p>Isopropyl Amine pka?</p>

Isopropyl Amine pka?

pka is approximately 35

13
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<p>Alkane pka?</p>

Alkane pka?

pka is approximately 60

14
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<p>Alkene pka?</p>

Alkene pka?

pka is approximately 44-45

15
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Alkyne bond energy for C-H bond?

125 Kcal/mol

16
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Alkene bond energy for C-H?

108 Kcal/mol

17
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Alkane bond energy for C-H?

100 Kcal/mol

18
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Allylic bond energy for C-H?

86 Kcal/mol

19
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Alcohol bond energy for O-H?

110 Kcal/mol

20
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Alkane bond energy for C-C?

82 Kcal/mol

21
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Alkene bond energy for C=C?

82+64 = 146 Kcal/mol

22
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Alkyne bond energy for C triple bond C?

82+64+64 = 210 Kcal/mol

23
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Ether bond energy for C-O?

85 Kcal/mol

24
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Keytone bond energy for C=O?

85+95 = 180 Kcal/mol

25
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Peroxide bond energy for O-O?

30-50 Kcal/mol

26
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Disulfide bond energy for S-S?

30-50 Kcal/mol

27
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Rotational bond energy for a alkane bond (C-C)?

2.9 Kcal/mol

28
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Rotational bond energy for an amide bond (C-N)?

17 Kcal/mol

29
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If the energy is greater than __ an isomer will not interconvert at room temperature (change from one isomer to another)

greater than 22 Kcal/mol

30
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Rank these carbonyl groups from acidic to basic:

Water

Aldehyde

Ester

Amide

Carboxylic Acid/Carboxylate ion

Keytone

Most Acidic Aldehyde > Keytone > Ester > Carboxylic Acid/Carboxylate ion > Water > Amide Most Basic

Lone pairs on the aldehyde carbonyl group make it a more acidic carbonyl than a carboxylic acid. Not looking at protons with this question strictly C=O acidity. Resonance stabilizes the charge through its other oxygen group for carboxylic acids making it more of a basic (stable) carbonyl group.

31
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A value for methyl

1.70

32
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A value for tert-butyl group

>4.5

33
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A value for PbMe3

0.7, longer bond length so it does not have much of a diaxial interaction