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"}ol.lst-kix_ub19s0tqph5s-0.start{counter-reset:lst-ctn-kix_ub19s0tqph5s-0 0}.lst-kix_r8sre4ceg0t7-4 > li:before{content:"o "}.lst-kix_r8sre4ceg0t7-6 > li:before{content:"● "}.lst-kix_cch2ocafejm5-7 > li:before{content:"o "}.lst-kix_l5p2f23q405o-1 > li:before{content:"" counter(lst-ctn-kix_l5p2f23q405o-1,lower-latin) ". "}.lst-kix_ub19s0tqph5s-7 > li{counter-increment:lst-ctn-kix_ub19s0tqph5s-7}.lst-kix_l5p2f23q405o-4 > li{counter-increment:lst-ctn-kix_l5p2f23q405o-4}.lst-kix_998hy2mr7bdx-3 > li:before{content:"● "}.lst-kix_uka1rlgx69n-2 > li:before{content:"▪ "}.lst-kix_r8sre4ceg0t7-0 > li:before{content:"• "}.lst-kix_r8sre4ceg0t7-2 > li:before{content:"▪ "}.lst-kix_998hy2mr7bdx-5 > li:before{content:"▪ "}.lst-kix_uka1rlgx69n-0 > li:before{content:"▪ "}ol.lst-kix_l5p2f23q405o-8.start{counter-reset:lst-ctn-kix_l5p2f23q405o-8 0}.lst-kix_a89tr7pr5ebl-8 > li:before{content:"▪ "}.lst-kix_a89tr7pr5ebl-6 > li:before{content:"● "}.lst-kix_998hy2mr7bdx-1 > li:before{content:"o "}.lst-kix_cch2ocafejm5-1 > li:before{content:"o "}.lst-kix_cch2ocafejm5-3 > li:before{content:"● "}.lst-kix_r8sre4ceg0t7-8 > li:before{content:"▪ "}.lst-kix_cch2ocafejm5-5 > li:before{content:"▪ "}
CHE 118C – Nasiri SSI 2017We also discuss several other topics like What is chromosome's structure made up of?
If you want to learn more check out Define polarizability.
Head TA : rasquitieri@ucdavis.ed
Calculated grade = (83+156)/ (54+116) x 58We also discuss several other topics like What is stated in coercive acts 1774?
Ch 19 Carboxylic Acids
Don't forget about the age old question of Is “word crimes” an effective study tool or is it mocking the teachings of grammar?
CH4
Combustion
Free radical halogenationWe also discuss several other topics like What is the content of eisenstadt versus baird (1972)?
pKa = 6O
CH4 + HCO3- → No reaction
- Carboxylic acid has highest priority
→ Hexanoic acidDon't forget about the age old question of What is a social condition, event, or pattern of behavior that negatively affects the well-being of a significant number of people (or several significant people) who believe the condition, event, or pattern needs to be changed or ameliorated?
- Name of hydrocarbon – € + (oic cid)

Example:
Common name:
p-aminobenzoic acid
Systematic name:
4-aminobenzenecarboxylic acid
Example:
→ 5-oxopentanoic acid

→ 5-exohexanal
Example:

→ 3-methyl cyclohexanecarboxylic acid
Naming dioc acids
Ethanedioic acid
Common name: oxalic acid

Weak base
Which is stronger acid?

Acetic acid Formic acid
- Electron pulling group increases acidity by induction effect
Which is stronger acid?

O and N can get involved in donating and resonance
- By resonance: e- donating
- By induction: e- withdrawing
- Will use resonance unless it is invaluable
Example: rank the following compound in order of increasing acidity (1 is strongest acid)

- Para/ortho have resonance
Para

Meta

Para

e- donating

B is stronger base because of resonance
Example: Rank the following in order of increasing basicity (1 is strongest base)

C and A are almost equal pKe
- Less steric hindrance = more available lone pair

- Must have lone pair to be able to accept H+ to become a base
- Must be accessible
- Synthesis of Carboxylic acids
- Oxidation of Primary alcohols (RCH2OH)


- Oxidation of RCCH3 (ketones)

- Reaction of organometallic compounds (RMg, RLI) with CO2





- Oxidation of dramatic compounds

- Reactions of CH2CO2H (Carboxylic Acids)

- Nucleophilic (Acyl) substitution
(Alconyl)

- Conversion of RCOH → RC-X (X= Cl, Br, I)

Side Note:
Acids:
- Nucleophilic Sn Hx(X=Cl,Br,I) RCO2H
- Non-nucleophilic

- Mechanism in basic medium:
- Reduction of RCOH into I alcohol (RCH2OH)

Mechanism:


- Intromolecular conversion

Butanedioic acid butanedioic anhydride
CN: succinic acid CN: succinic anhydride

- Fischer Esterification (only in acidic medium)


- Responsible for knowing the reverse reaction as well (it is exactly the same but going the opposite direction)

Mechanism:


- Please don’t use this reaction for synthesis of amide on exams! ( it is not practical in practice)
- Hell-Volnard-Zelinsky Reaction

Mechanism:
Step 1: formation of RCH2CBr

Step 2:


Ch 20: Derivatives of Carboxylic acids

- C,N,O all have 2p∞ orbitals so they are compatible

- Resonance shortens bond length
- Derivatives of RCO2H naming, Synthesis and Reactions
- Arkoryl halides are most reactive because:
- C=O most e- deficient
- LG ability is highest




- Most reactive derivative can easily go to less reactive derivative
Never Happens
- Reactions of Acyl Hallides
Primary alcohol
Aldehyde
Ketone
Anhydride
Esters
Amide
Symmetrical alcohol (2 identical R groups hydrolyzed)
-
Carboxyl acid is the mother of all organic compounds
- Alkonoyl halide is very reactive with H2O
- Every carboxylic acid derivative will carry out this reaction (8) by hydrolysis
- Reduction to 1+OH (RCH2OH)
- The only derivative that works with both NaBH4 acid LiAlH4 → usually not reactive
Mechanism:

- Reduction to aldehyde (RCH)
- Must have less reactive reducing agent

- This reducing agent is less reactive because of steric hindrance

- Conversion to Ketones (RCR)

→ cannot use very reactive organo metallic compound: it will react with the aldehyde and ketone, so use organo cuprate (which is made from organo lithium)

- Conversion into Anhydrides (RCOCR)

Mechanisms: Nucleophilic Addition and Elimination

- Reduction to esters (RCOR)

- Reduction to amides (RCN)

Stoichiometric ration is given
Mechanism:

- Another amine → N must have at least 1 H
