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"}.lst-kix_vfbrebmhauhm-0 > li:before{content:"→ "}ol.lst-kix_ub19s0tqph5s-4.start{counter-reset:lst-ctn-kix_ub19s0tqph5s-4 0}.lst-kix_l5p2f23q405o-2 > li:before{content:"" counter(lst-ctn-kix_l5p2f23q405o-2,lower-roman) ". 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"}ol.lst-kix_ub19s0tqph5s-1{list-style-type:none}.lst-kix_ub19s0tqph5s-5 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-5,lower-roman) ". "}.lst-kix_ub19s0tqph5s-7 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-7,lower-latin) ". "}ol.lst-kix_ub19s0tqph5s-0{list-style-type:none}.lst-kix_ub19s0tqph5s-3 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-3,decimal) ". "}.lst-kix_ub19s0tqph5s-4 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-4,lower-latin) ". "}ul.lst-kix_a89tr7pr5ebl-0{list-style-type:none}ul.lst-kix_a89tr7pr5ebl-1{list-style-type:none}ul.lst-kix_a89tr7pr5ebl-4{list-style-type:none}ul.lst-kix_a89tr7pr5ebl-5{list-style-type:none}ul.lst-kix_a89tr7pr5ebl-2{list-style-type:none}ul.lst-kix_a89tr7pr5ebl-3{list-style-type:none}.lst-kix_ub19s0tqph5s-2 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-2,lower-roman) ". "}ol.lst-kix_ub19s0tqph5s-5.start{counter-reset:lst-ctn-kix_ub19s0tqph5s-5 0}ol.lst-kix_l5p2f23q405o-3.start{counter-reset:lst-ctn-kix_l5p2f23q405o-3 0}ul.lst-kix_a89tr7pr5ebl-8{list-style-type:none}.lst-kix_ub19s0tqph5s-1 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-1,lower-latin) ". "}ul.lst-kix_a89tr7pr5ebl-6{list-style-type:none}ul.lst-kix_a89tr7pr5ebl-7{list-style-type:none}.lst-kix_ub19s0tqph5s-0 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-0,decimal) ") "}.lst-kix_l5p2f23q405o-1 > li{counter-increment:lst-ctn-kix_l5p2f23q405o-1}.lst-kix_ub19s0tqph5s-1 > li{counter-increment:lst-ctn-kix_ub19s0tqph5s-1}.lst-kix_l5p2f23q405o-3 > li{counter-increment:lst-ctn-kix_l5p2f23q405o-3}.lst-kix_ub19s0tqph5s-8 > li:before{content:"" counter(lst-ctn-kix_ub19s0tqph5s-8,lower-roman) ". "}.lst-kix_l5p2f23q405o-5 > li:before{content:"" counter(lst-ctn-kix_l5p2f23q405o-5,lower-roman) ". "}.lst-kix_l5p2f23q405o-6 > li:before{content:"" counter(lst-ctn-kix_l5p2f23q405o-6,decimal) ". "}.lst-kix_q7jx6yt6m6wv-7 > li:before{content:"o "}.lst-kix_q7jx6yt6m6wv-8 > li:before{content:"▪ "}.lst-kix_l5p2f23q405o-8 > li:before{content:"" counter(lst-ctn-kix_l5p2f23q405o-8,lower-roman) ". "}.lst-kix_l5p2f23q405o-5 > li{counter-increment:lst-ctn-kix_l5p2f23q405o-5}.lst-kix_l5p2f23q405o-7 > li:before{content:"" counter(lst-ctn-kix_l5p2f23q405o-7,lower-latin) ". "}.lst-kix_q7jx6yt6m6wv-3 > li:before{content:"● "}.lst-kix_q7jx6yt6m6wv-2 > li:before{content:"▪ "}.lst-kix_q7jx6yt6m6wv-4 > li:before{content:"o "}.lst-kix_q7jx6yt6m6wv-6 > li:before{content:"● "}.lst-kix_q7jx6yt6m6wv-5 > li:before{content:"▪ "}ol.lst-kix_l5p2f23q405o-6{list-style-type:none}ol.lst-kix_l5p2f23q405o-7{list-style-type:none}ol.lst-kix_l5p2f23q405o-4{list-style-type:none}ol.lst-kix_l5p2f23q405o-5{list-style-type:none}ol.lst-kix_l5p2f23q405o-8{list-style-type:none}.lst-kix_q7jx6yt6m6wv-0 > li:before{content:"• "}ol.lst-kix_l5p2f23q405o-2{list-style-type:none}.lst-kix_q7jx6yt6m6wv-1 > li:before{content:"o "}ol.lst-kix_l5p2f23q405o-3{list-style-type:none}ol.lst-kix_l5p2f23q405o-0{list-style-type:none}ol.lst-kix_l5p2f23q405o-1{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-8{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-7{list-style-type:none}ol.lst-kix_ub19s0tqph5s-7{list-style-type:none}.lst-kix_ub19s0tqph5s-8 > li{counter-increment:lst-ctn-kix_ub19s0tqph5s-8}ul.lst-kix_r8sre4ceg0t7-0{list-style-type:none}ol.lst-kix_ub19s0tqph5s-6{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-2{list-style-type:none}ol.lst-kix_ub19s0tqph5s-8{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-1{list-style-type:none}ol.lst-kix_ub19s0tqph5s-3{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-4{list-style-type:none}ol.lst-kix_ub19s0tqph5s-2{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-3{list-style-type:none}ol.lst-kix_ub19s0tqph5s-5{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-6{list-style-type:none}ol.lst-kix_ub19s0tqph5s-4{list-style-type:none}ul.lst-kix_r8sre4ceg0t7-5{list-style-type:none}.lst-kix_vfbrebmhauhm-1 > li:before{content:"o "}ol.lst-kix_l5p2f23q405o-7.start{counter-reset:lst-ctn-kix_l5p2f23q405o-7 0}.lst-kix_fbue3u31cx0k-8 > li:before{content:"▪ "}ul.lst-kix_q7jx6yt6m6wv-8{list-style-type:none}ul.lst-kix_q7jx6yt6m6wv-7{list-style-type:none}.lst-kix_vfbrebmhauhm-5 > li:before{content:"▪ "}ul.lst-kix_q7jx6yt6m6wv-6{list-style-type:none}ul.lst-kix_q7jx6yt6m6wv-5{list-style-type:none}ul.lst-kix_q7jx6yt6m6wv-4{list-style-type:none}ul.lst-kix_q7jx6yt6m6wv-3{list-style-type:none}.lst-kix_vfbrebmhauhm-3 > li:before{content:"● "}ul.lst-kix_q7jx6yt6m6wv-2{list-style-type:none}.lst-kix_fbue3u31cx0k-2 > li:before{content:"▪ "}ul.lst-kix_q7jx6yt6m6wv-1{list-style-type:none}ul.lst-kix_q7jx6yt6m6wv-0{list-style-type:none}.lst-kix_a89tr7pr5ebl-0 > li:before{content:"❖ "}.lst-kix_a89tr7pr5ebl-2 > li:before{content:"▪ "}.lst-kix_fbue3u31cx0k-4 > li:before{content:"o "}.lst-kix_a89tr7pr5ebl-4 > li:before{content:"o "}.lst-kix_vfbrebmhauhm-7 > li:before{content:"o "}.lst-kix_fbue3u31cx0k-6 > li:before{content:"● "}.lst-kix_uka1rlgx69n-6 > li:before{content:"● "}.lst-kix_ub19s0tqph5s-6 > li{counter-increment:lst-ctn-kix_ub19s0tqph5s-6}ol.lst-kix_ub19s0tqph5s-1.start{counter-reset:lst-ctn-kix_ub19s0tqph5s-1 0}.lst-kix_uka1rlgx69n-4 > li:before{content:"o "}.lst-kix_fbue3u31cx0k-0 > li:before{content:"o "}.lst-kix_uka1rlgx69n-8 > li:before{content:"▪ "}.lst-kix_l5p2f23q405o-3 > li:before{content:"" counter(lst-ctn-kix_l5p2f23q405o-3,decimal) ". "}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

• Naming

• 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

• Acidity

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

• Basicity

  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 RCH

• Oxidation of RCCH3 (ketones)

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

• Mechanism

• Hydrolysis of RCN

• Synthesis of RCN

• Other example

• Oxidation of dramatic compounds

• Reactions of         CH2CO2H (Carboxylic Acids)

• Nucleophilic (Acyl) substitution

 (Alconyl)

• Mechanism

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

Side Note:

Acids:

• Nucleophilic  Sn  Hx(X=Cl,Br,I) RCO2H
• Non-nucleophilic

• Mechanism:

• Mechanism in basic medium:
  

• Reduction of RCOH into I alcohol (RCH2OH)

Mechanism:

• Conversion into RCOCR

• Intromolecular conversion

        Butanedioic acid                        butanedioic anhydride

        CN: succinic acid                        CN: succinic anhydride

• Conversion into ester

• Fischer Esterification (only in acidic medium)

• Reversible reaction

• Mechanism:

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

• Conversion of RCO2HCH3

Mechanism:

• Conversion into Amides

• 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:

1. C=O most e- deficient
2. LG ability is highest

• Relative reactivity

• Naming for Acyl Halode

• Open chain acyl halide:

• In ring

• Synthesis of Acyl Halide

• 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

1. Reduction to 1+OH (RCH2OH)

• The only derivative that works with both NaBH4 acid LiAlH4 → usually not reactive
  

Mechanism:

1. Reduction to aldehyde (RCH)

• Must have less reactive reducing agent

• This reducing agent is less reactive because of steric hindrance

1. 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)

1. Conversion into Anhydrides (RCOCR)

Mechanisms: Nucleophilic Addition and Elimination

1. Reduction to esters (RCOR)

1. Reduction to amides (RCN)

Stoichiometric ration is given

Mechanism:

• Another amine → N must have at least 1 H

References: