Test 3 Review PDF

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Unit 7 ● Carboxylic Acids ○ Formula: R-COOH ○ Replace the ‘e’ ending with ‘oic acid’ ○ ortho (o) = 1,2 on the ring ○ meta (m) = 1,3 on the ring ○ para (p) = 1,4 on the ring ○ React with strong bases to form carboxylate salts ○ React with alcohols to produce ester and water ● Esters ○ Formula: R-COO-R ○ Replace ‘oic acid’ with ‘oate’ ○ Naming ■ Alcohol side (R-C=O) 1st then everything else ○ Acid hydrolysis produce carboxylic acid and alcohol

Unit 8 ● Amines ○ Formula: ■ Tertiary amines do not hydrogen bond to each other

○ Replace the ‘e’ ending with amines ■ Aromatic Amines ● The amine of benzene is named aniline (Systematic name = benzenamine) ■ Common Name ● Name the alkyl groups attached to the N in alphabetical order ● Add –amine ● The name is continuous, no spaces between groups ■ Alkylammonium Salts ● Name amine salts by replacing the suffix – amine with ammonium ● Add the name of the anion ● Converting amines to salts often makes insoluble amines soluble as the salts are ionic

○ Amines are weak bases ■ accept H+ when dissolved in water ○ boiling points between alkanes and alcohols ■ Tertiary amines boil lower than 1o or 2o of similar molecular weight ○ Heterocyclic Amines ■ Cyclic compounds ■ Have at least one double bond in the ring ● Amides ○ a reaction between a carboxylic acid derivative and an amine or ammonia ○ Formula:

○ Replace the ‘e’ ending with amides ■ Names are derived from the carboxylic acid ● Remove –oic acid and replace with –amide ■ Nitrogen substituents are prefixed to the name ● indicated by N○ Amides hydrolyze with: ■ Acid to produce ● Carboxylic acid ● Amine salt ■ Base to produce ● Carboxylic acid salt ● Amine o o ○ 1 and 2 amines react with acid chlorides and acid anhydrides to produce amides ○ Most amides are solids at room temperature due to internal hydrogen bonding

Other Important Information ● Common Name ○ Carboxylic Acids ■ Benzene → Benzoic Acid ■ Sodium acetate (Sodium ethanoate) ■ Acetic acid (ethanoic acid) ■ Butyric acid (butanoic acid) ■ Sodium propanoate or sodium propionate (sodium + propanoic acid)

○ Esters ■ Ethyl butyrate (ethyl butanoate) ■ Propyl propionate (propyl propanoate) ■ Propyl acetate (propyl ethanoate)

○ Amines ■ Methylamine (methanamine) ■ Dimethylamine (N, N - methanamine) ■ Trimethylamine (N, N - dimethylmethanamine) ■ Ethylamine (ethanamine) ■ Propylamine (propanamine) ■ butylamine (butanamine)

○ Amides ■ Ethanoic acid/acetic acid (ethanamide/acetamide)

■ ■ ■ ■ ■ ■

Propanoic acid/Propionic acid (propanamide/propionamide) Formamide (methanamide) Acetamide (ethanamide) Propionamide (propanamide) N-Methylformamide (N-Methylmethanamide) N-Methyacetamide (N-Methylethanamide)

● Remember* ○ Oxidizing Agent: Chromic Acid (H2CrO4) ○ Carboxylic Acids ■ Formula: R - COOH ■ Replace the ‘e’ ending with ‘oic acid’ ■ ortho (o) = 1,2 on the ring ■ meta (m) = 1,3 on the ring ■ para (p) = 1,4 on the ring ■ Carboxylate Salts ● Carboxylic Acids reacting with strong bases (NaOH) ● Replace ‘oic acid’ with ‘ate’ ● Formula: R-COO- Cation+ ■ React with alcohols to produce ester and water ○ Esters ■ Formula: R-COO-R ■ Replace ‘oic acid’ with ‘oate’ ■ Naming ● Alcohol side (R-C=O/R-CO) = yl ending ● Carboxylic side (C=OO-R/COO-R) = oate ending ■ Acid hydrolysis produce carboxylic acid and alcohol ● with heat and sulphuric acid (H2SO4) ● carboxylic acid and alcohol = heat and sulphuric acid ( H2SO4) ○ Amines ■ Formula: ● Tertiary amines do not hydrogen bond to each other

■ Replace the ‘e’ ending with amines ● Aromatic Amines ○ The amine of benzene is named aniline (Systematic name =

benzenamine) ● Common Name ○ Name the alkyl groups attached to the N in alphabetical order ○ Add –amine ○ The name is continuous, no spaces between groups ● Alkylammonium Salts ○ Name amine salts by replacing the suffix – amine with ammonium ○ Add the name of the anion ○ Converting amines to salts often makes insoluble amines soluble as the salts are ionic ○ Amides ■ Formula:

■ Replace the ‘e’ ending with amides ● Names are derived from the carboxylic acid ○ Remove –oic acid and replace with –amide ● Nitrogen substituents are prefixed to the name ○ indicated by N-

Unit 7 Summary of Reactions

Unit 8 Summary of Reactions

Unit 9 Charts NMR Chart

IR Chart

Unit 9 Guidelines 1. Look at the chemical formula for specific atoms (oxygen and/or nitrogen)

2. Check the FTIR spectra for functional groups related to the atoms found in the chemical formula a. If oxygen present, check for: i. ≈ 3400 cm -1 , big and broad “tongue” (Alcohol, O-H stretch) ii. ≈ 3400 cm -1 , big and very broad “hair beard” (Carboxylic acid, O-H stretch) iii. ≈ 1725 cm -1 , big and narrow “sword” (Carbonyl, C=O stretch) iv. ≈ 1150 cm -1 , big and narrow (Alcohol or ether, C-O stretch) b. If nitrogen present, check for: i. ≈ 3400 cm -1 , double peak (1 o amine) or single peak (2 o amine) N-H stretch ii. ≈ 1675 cm -1 , carbonyl peak also present indicates there’s an amide c. One last significant area to check: i. ＞ 3000 cm -1 , C=C present and likely in a ring (sp 2 hybridized C-H stretch) ii. ＜ 3000 cm -1 , C-C present (sp 3 hybridized C-H stretch) 3. 3. After identifying what functional groups are present, return to the chemical formula and draw all possible isomers of the compound. If this isn’t possible or there are too many possibilities refer to the NMR integration. 4. Refer to the integration on the NMR spectrum, remember chemically equivalent protons! a. 1H – commonly refers to a CH or OH b. 2H – commonly refers to CH 2 c. 3H – refers to CH 3 d. 4H – refers to 2 CH 2 groups with chemically equivalent protons e. 6H – refers to 2 CH 3 groups with chemically equivalent protons (iso-) f. Even #＞ 6H – refers to carbon chain with many CH 2 5. Draw the compound and confirm identity with NMR integration and downfield shifts (ppm) TL;DR 1. Look at the atoms in the chemical formula 2. Check IR for functional groups related to atoms 3. Draw possible structures 4. Check NMR integration, identify alkyl groups 5. Determine compound...