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There are general four ways for pushing electrons between substances

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Presentation on theme: "There are general four ways for pushing electrons between substances"— Presentation transcript:

1 There are general four ways for pushing electrons between substances
Law of Electrostatics full negative full positive full negative partial positive full positive partial negative partial positive partial negative

2 Law of Electrostatics - Example 1
full negative full positive

3 Law of Electrostatics - Example 1
full negative full positive

4 Law of Electrostatics - Example 2
full positive partial negative

5 Law of Electrostatics - Example 2
full positive partial negative

6 Law of Electrostatics - Example 3
full negative partial positive

7 Law of Electrostatics - Example 3
full negative partial positive

8 Law of Electrostatics - Example 4
partial positive partial negative

9 Law of Electrostatics - Example 4
partial positive partial negative

10 Balancing of Reactions (rxns)
A, e-, FC = Atoms, Electrons & Formal Charges Must Balance A e- FC must balance 4 carbons, 9 hydrogens 1 bromine 4 carbons, 9 hydrogens 1 bromine 14 electrons drawn 14 electrons drawn 0 zero overall charge + formal & - formal charges sum to zero overall charge 0 zero overall charge

11 Balancing of Reactions (rxns)
A, e-, FC = Atoms, Electrons & Formal Charges Must Balance A e- FC must balance 4 carbons, 11 hydrogens 1 oxygen 4 carbons, 11 hydrogens 1 oxygen 14 electrons drawn 14 electrons drawn + formal charge + formal charge

12 For these reactions, are A, e-, FC balanced ???
Yes, for both rxns

13 Not so obvious electron pushing rxns students struggle with

14 Not so obvious electron pushing rxns students struggle with
boron in BH3 disobeys octet rule, 8K

15 Not so obvious electron pushing rxns students struggle with
boron in BH3 disobeys octet rule, 8K

16 Not so obvious electron pushing rxns students struggle with
boron in BH3 disobeys octet rule, 8K boron above now obeys octet rule, 8K “Octet rule is king!”

17 Not so obvious electron pushing rxns students struggle with
aluminum in AlH3 disobeys octet rule, 8K

18 Not so obvious electron pushing rxns students struggle with
aluminum in AlH3 disobeys octet rule, 8K

19 Not so obvious electron pushing rxns students may struggle with
aluminum above now obeys octet rule, 8K “Octet rule is king!” aluminum in AlH3 disobeys octet rule, 8K

20 Not so obvious electron pushing rxns students may struggle with.
Nonbonded electron pairs love to be protonated !!!!! Which nonbonded pair of electrons below like to be protonated? carbonyl oxygen hydroxyl oxygen

21 Not so obvious electron pushing rxns students may struggle with.
Nonbonded electron pairs love to be protonated !!!!! Which nonbonded pair of electrons below like to be protonated?

22 Not so obvious electron pushing rxns students may struggle with.
Nonbonded electron pairs love to be protonated !!!!! Which nonbonded pair of electrons below like to be protonated?

23 Not so obvious electron pushing rxns students may struggle with.
Nonbonded electron pairs love to be protonated !!!!! Which nonbonded pair of electrons below like to be protonated?

24 Not so obvious electron pushing rxns students may struggle with.
Nonbonded electron pairs love to be protonated !!!!! Which nonbonded pair of electrons below like to be protonated?

25 Not so obvious electron pushing rxns students may struggle with.
Nonbonded electron pairs love to be protonated !!!!! Which nonbonded pair of electrons below like to be protonated? Explain why the carbonyl oxygen in the first reaction preferentially gets protonated over the hydroxyl group in acetic acid. Protonation of the carbonyl in acetic acid produces a resonance stabilized intermediate where as in the other case the intermediate will have an isolated positive charge on its hydroxyl group.

26 Not so obvious electron pushing rxns students may struggle with

27 But where is the electron pair in the alkene
Not so obvious electron pushing rxns students may struggle with Reactions of pi bonds in alkenes Pi bond basic because a ”pi bond” can show chemical behavior as a base according to our three definintions for acids-bases. pi bonds can behave as a Lewis base electron pair donor pi bonds can behave as a Brownsted-Lowery base H+ acceptor But where is the electron pair in the alkene capable of donating then accepting a proton? • •

28 The electron pair is being share between the
Not so obvious electron pushing rxns students may struggle with • • The electron pair is being share between the two carbons C=C bond and the pi bond basic is capable electron donation and H+ accepting.

29 Not so obvious electron pushing rxns students may struggle with
unstable carbocation disobeys octet rule, 8K

30 Ochem I Reactions - Many rxns this semester can be labeled as either:
Acid-Base (Ch 2) Brownsted-Lowery - BLAB happy & know it - donate it, H+ Lewis Acid-Base Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective) SN2 (Ch 11) primary halides Eliminations alkene synthesis dehydration of alcohols acid catalyzed conditions dehydrohalogation, E2 basic dehalogenation of vicinal dihalides neutral Additions (Ch 7, 8, 9) radical additions HBr/ROOR electrophilic addition pi bond basic

31 Reactions this semester can be labeled as:
Acid-Base (Ch 2) Brownsted-Lowery - BLAB happy & know it - donate it, H+ your pKa will clearly show it Lewis Acid-Base

32 Reactions this semester can be labeled as:
Acid-Base (Ch 2) Brownsted-Lowery - BLAB happy & know it - donate it, H+ your pKa will clearly show it Lewis Acid-Base

33 Reactions this semester can be labeled as:
Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective) SN2 (Ch 11) primary halides

34 Reactions this semester can be labeled as:
HIGH instability Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective) Groud state

35 Reactions this semester can be labeled as:
Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective)

36 Reactions this semester can be labeled as:
Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective)

37 Reactions this semester can be labeled as:
Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective)

38 Reactions this semester can be labeled as:
Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective)

39 Reactions this semester can be labeled as:
Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective)

40 Reactions this semester can be labeled as:
Substitutions (Ch 6) radical substitutions radical stability trend Cl2/hv (nonselective) Br2/hv (selective)

41 Looking for CLUES CLUES Substrate conditions alkane alkene

42 Looking for CLUES CLUES Substrate conditions alkane alkene

43 Looking for CLUES CLUES Substrate conditions alkane alkene

44 Looking for CLUES CLUES Substrate conditions alkene Additions (Ch 7, 8, 9) radical additions HBr/ROOR electrophilic addition pi bond basic

45 Looking for CLUES CLUES Substrate conditions alkene Additions (Ch 7, 8, 9) radical additions HBr/ROOR electrophilic addition pi bond basic

46 Reactions this semester can be labeled as:
Additions (Ch 7, 8, 9) radical additions HBr/ROOR electrophilic addition pi bond basic

47 Reactions this semester can be labeled as:
Additions (Ch 7, 8, 9)

48 Reactions this semester can be labeled as:
Additions (Ch 7, 8, 9) radical additions HBr/ROOR electrophilic addition pi bond basic

49 Ochem I Reactions - Many rxns this semester can be labeled as either:
Eliminations alkene synthesis dehydration of alcohols acid catalyzed conditions dehydrohalogation, E2 basic dehalogenation of vicinal dihalides neutral

50 Reactions this semester can be labeled as:
Eliminations alkene synthesis dehydration of alcohols acid catalyzed conditions dehydrohalogation, E2 basic dehalogenation of vicinal dihalides neutral

51 Reactions this semester can be labeled as:
Eliminations alkene synthesis dehydration of alcohols acid catalyzed conditions dehydrohalogation, E2 basic dehalogenation of vicinal dihalides neutral

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