10- CARBOXYLIC ACIDS & DERIVATIVES

d. Electron-poor carbonyl carbon = welcomes nucleophiles

Reactivity property of carboxylic acids and derivatives describing their carbonyl carbon

a. Electron-rich carbonyl carbon = welcomes electrophiles
b. Electron-poor carbonyl carbon = welcomes electrophiles
c. Electron-rich carbonyl carbon = welcomes nucleophiles
d. Electron-poor carbonyl carbon = welcomes nucleophiles

c. Nucleophilic Acyl Substitution

Common mechanism for reactions of carboxylic acids and derivatives

a. Electrophilic Aromatic Substitution
b. Nucleophilic Addition
c. Nucleophilic Acyl Substitution
d. Free Radical Substitution

d. Formic

Monocarboxylic acid with 1 carbon

a. Acetic
b. Propionic
c. Butyric
d. Formic

c. Acetic

Monocarboxylic acid with 2 carbons

a. Formic
b. Propionic
c. Acetic
d. Butyric

d. Propionic

Monocarboxylic acid with 3 carbons

a. Butyric
b. Acetic
c. Valeric
d. Propionic

b. Butyric

Monocarboxylic acid with 4 carbons

a. Valeric
b. Butyric
c. Caproic
d. Propionic

d. Valeric

Monocarboxylic acid with 5 carbons

a. Caproic
b. Butyric
c. Enanthic
d. Valeric

c. Caproic

“Capr6ic”

Monocarboxylic acid with 6 carbons

a. Enanthic
b. Capric
c. Caproic
d. Caprylic

d. Enanthic

Monocarboxylic acid with 7 carbons

a. Caprylic
b. Caproic
c. Pelargonic
d. Enanthic

d. Caprylic

“eyt=8” → “Caprylic”

Monocarboxylic acid with 8 carbons

a. Pelargonic
b. Caproic
c. Capric
d. Caprylic

c. Pelargonic

Monocarboxylic acid with 9 carbons

a. Capric
b. Caprylic
c. Pelargonic
d. Caproic

a. Capric

Monocarboxylic acid with 10 carbons

a. Capric
b. Caproic
c. Caprylic
d. Enanthic

b. Oxalic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 2 carbons

a. Malonic
b. Oxalic
c. Succinic
d. Glutaric

c. Malonic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 3 carbons

a. Oxalic
b. Succinic
c. Malonic
d. Glutaric

d. Succinic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 4 carbons

a. Malonic
b. Glutaric
c. Oxalic
d. Succinic

d. Glutaric

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 5 carbons

a. Adipic
b. Succinic
c. Pimelic
d. Glutaric

a. Adipic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 6 carbons

a. Adipic
b. Pimelic
c. Glutaric
d. Suberic

c. Pimelic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 7 carbons

a. Adipic
b. Suberic
c. Pimelic
d. Azelaic

d. Suberic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 8 carbons

a. Pimelic
b. Azelaic
c. Sebacic
d. Suberic

c. Azelaic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 9 carbons

a. Suberic
b. Sebacic
c. Azelaic
d. Pimelic

d. Sebacic

“2C-10C → Oh My Such Good Apple Pie Sweet As Sugar”

Dicarboxylic acid with 10 carbons

a. Azelaic
b. Suberic
c. Pimelic
d. Sebacic

c. Conversion to Acyl Halides

Reaction of carboxylic acids involving conversion to acyl halides using SOCl₂

a. Esterification
b. Aminolysis
c. Conversion to Acyl Halides
d. Hydration

d. SOCl₂

Reagent used to convert R-COOH to an acyl halide (R-C=O-Cl)

a. PBr₃
b. KOH
c. NH₃
d. SOCl₂

c. Acyl halide

Product formed when R-COOH reacts with SOCl₂

a. Ester
b. Amide
c. Acyl halide
d. Alcohol

c. Esterification/Alcoholysis

Reaction of carboxylic acids with R'OH to produce an ester

a. Aminolysis
b. Hydration
c. Esterification/Alcoholysis
d. Conversion to Acyl Halides

c. Alcoholysis

Another name for Esterification

a. Aminolysis
b. Hydrolysis
c. Alcoholysis
d. Acylation

d. Ester

Product formed when R-COOH reacts with R'OH during Esterification

a. Amide
b. Acyl halide
c. Alcohol
d. Ester

d. Conversion to Amides/Aminolysis

Reaction of carboxylic acids with NH₃ to produce an amide

a. Esterification
b. Conversion to Acyl Halides
c. Hydrolysis
d. Conversion to Amides/Aminolysis

c. Ammonium salt (R-COO⁻NH₄⁺)

Initial product formed at room temperature when R-COOH reacts with NH₃

a. Amide
b. Acyl halide
c. Ammonium salt (R-COO⁻NH₄⁺)
d. Ester

d. 500°C

Temperature required for Aminolysis (direct method) to convert the ammonium salt to an amide

a. 100°C
b. 200°C
c. 300°C
d. 500°C

c. Two

Number of processes available for Conversion to Amides/Aminolysis

a. Four
b. Three
c. Two
d. One

b. R-COOH → Acyl halide (R-C=O-Cl) via SOCl₂

First step of the alternative process for Conversion to Amides using SOCl₂

a. R-COOH + NH₃ → Amide directly
b. R-COOH → Acyl halide (R-C=O-Cl) via SOCl₂
c. R-COOH + R'OH → Ester
d. R-COOH → Ammonium salt via NH₃

c. Acyl halide + NH₃ → Amide

Second step of the alternative process for Conversion to Amides after forming the acyl halide

a. Acyl halide + R'OH → Ester
b. Acyl halide + H₂O → Carboxylic acid
c. Acyl halide + NH₃ → Amide
d. Acyl halide + KOH → Alcohol

c. R-COOH + NH₃ → Ammonium salt → (500°C) → Amide

Correct sequence of the direct method for Conversion to Amides

a. R-COOH + NH₃ → Amide (room temp, no heat needed)
b. R-COOH + SOCl₂ → Acyl halide + NH₃ → Amide
c. R-COOH + NH₃ → Ammonium salt → (500°C) → Amide
d. R-COOH + R'OH → Ester + NH₃ → Amide

b. R-COOH + SOCl₂ → Acyl halide + NH₃ → Amide

Correct sequence of the alternative method for Conversion to Amides

a. R-COOH + NH₃ → Ammonium salt → (500°C) → Amide
b. R-COOH + SOCl₂ → Acyl halide + NH₃ → Amide
c. R-COOH + R'OH → Ester + NH₃ → Amide
d. R-COOH + H₂O → Hydrate + NH₃ → Amide

d. Hydrolysis

Reaction of all carboxylic acid derivatives involving addition of H₂O to produce a carboxylic acid and a leaving group

a. Saponification
b. Esterification
c. Aminolysis
d. Hydrolysis

b. Carboxylic acid and leaving group

Product formed when any carboxylic acid derivative undergoes Hydrolysis

a. Ester and alcohol
b. Carboxylic acid and leaving group
c. Amide and water
d. Acyl halide and amine

c. Saponification

Base-mediated hydrolysis of carboxylic acid derivatives

a. Aminolysis
b. Alcoholysis
c. Saponification
d. Esterification

d. NaOH and H₂O

Reagents used in Saponification of carboxylic acid derivatives

a. H₂O and HCl
b. SOCl₂ and H₂O
c. NH₃ and H₂O
d. NaOH and H₂O

c. Na⁺ (soap)

Product formed when a carboxylic acid derivative undergoes Saponification using NaOH and H₂O

a. Amide
b. Ester
c. Na⁺ (soap)
d. Acyl halide

d. LiAlH₄

Strong reducing agent used to reduce a carboxylic acid (RCOOH) to an aldehyde then to a primary alcohol

a. NaBH₄
b. K₂Cr₂O₇
c. PCC
d. LiAlH₄

a. RCOOH → Aldehyde → Primary alcohol

Correct sequence of products in the Redox (reduction) of carboxylic acids using LiAlH₄

a. RCOOH → Aldehyde → Primary alcohol
b. RCOOH → Primary alcohol → Aldehyde
c. RCOOH → Ketone → Secondary alcohol
d. RCOOH → Aldehyde → Secondary alcohol

d. Primary alcohol

Final product formed when a carboxylic acid undergoes complete reduction using LiAlH₄

a. Secondary alcohol
b. Aldehyde
c. Ketone
d. Primary alcohol

c. NaBH₄

Weak reducing agent used to achieve reduction to aldehyde only from carboxylic acids

a. LiAlH₄
b. K₂Cr₂O₇
c. NaBH₄
d. KMnO₄

d. Aldehyde only

Product formed when a carboxylic acid is reduced using NaBH₄

a. Primary alcohol
b. Ketone
c. Secondary alcohol
d. Aldehyde only

c. LiAlH₄ produces primary alcohol; NaBH₄ produces aldehyde only

Key distinction between LiAlH₄ and NaBH₄ as reducing agents for carboxylic acids

a. LiAlH₄ produces aldehyde only; NaBH₄ produces primary alcohol
b. Both produce primary alcohol as final product
c. LiAlH₄ produces primary alcohol; NaBH₄ produces aldehyde only
d. Both produce aldehyde as final product

d. Saponification

Among Hydrolysis and Saponification, the one that is base-mediated is

a. Both Hydrolysis and Saponification
b. Hydrolysis
c. Neither; both are acid-mediated
d. Saponification