CHEM 238 Lab Final Exam Quizlet (2023 Spring)

Based on the set of carbocations (see the results worksheet and final exam review video image), rank the carbocations from least to most stable.

F < C < B < A < E < D (I think)

Lab #1 Pre-Lab Question #5: For the Ferric Chloride Test, the deeper the color produced, the more acetylsalicylic acid. True or False.

False

Lab #2 Pre-Lab Question #3: Isoborneol is the endo product. True or False.

False

Lab #6 Pre-Lab Question #1: When performing a simple distillation, you should keep boiling the liquid until the container is dry and empty. True or False.

False

Lab #7 Pre-Lab Question #2: For the extraction portion of the Derivatives of Carboxylic Acids experiment, the top layer will be the aqueous layer and the bottom layer will be the organic layer. True or False.

False

Lab #9 Pre-Lab Question #5: Wash acetone and reagent-grade acetone are the same. True or False.

False

Based on Safety Case Study #4, acryoyl chloride doesn't spread quickly in the environment. True or False.

False, it is volatile and spreads quickly

The baeyer-dewsen synthesis is used for large scale commercial production. True or False.

False, the pfleger synthesis is used for this

At low temperatures the reaction is under _________________ control whereas at high temperatures the reaction is under __________________ control.

kinetic; thermodynamic

The lower the change in Gibbs Free energy, the ____________ (lower/higher) the path is in energy and the lower the free energy, the ____________ (lower/higher) the stability.

lower; higher (I think)

What are the 2 Category II carboxylic acid derivatives?

Aldehydes & Ketones

Which category of the derivatives of carboxylic acids can have a group be replaced by a Nucelophile?

Category I

In a carbonyl functional group, the carbon has a partial ____ charge and the oxygen has a partial ____ charge.

+; -

Lab #4 Discussion Worksheet Kinetic vs Thermodynamic Question #2: Rank the carbocation intermediates from least stable to most stable (see discussion questions). which is the kinetic control carbocation intermediate?

- The secondary carbocation is more stable than the primary carbocation. - The secondary carbocation is the kinetic control carbocation intermediate.

The kinetic product is always the _________ conjugate addition product.

1,2

What are the 4 Category 1 carboxylic acid derivatives?

1. Acid Chloride 2. Anhydride 3. Ester 4. Amide

What are two reactions by which indigo is produced?

1. Bayer-Dewsen Synthesis 2. Pfleger Synthesis

Lab #1 Discussion Questions #3: Describe three advantages of preparing natural products through chemical synthesis, as opposed to harvesting them from the natural source.

1. Chemical synthesis allows from higher purity than harvesting 2. Chemical synthesis can be scaled if large quantities are needed 3. Chemical synthesis has less detrimental impact on the environment, making it more sustainable

What are the steps and reagents used in the borohydride reduction of camphor reaction?

1. NaBH4, EtOH 2. H2O

What 4 Factors affects a carbocation's stability?

1. Number of adjacent alkyl groups - increased number of groups means more charge dispersal between bonds 2. Adjacent pi bonds - allows for resonance hybrids to help delocalize charge 3. Adjacent atoms with lone pairs - gives electrons to satisfy the octet 4. Electron withdrawing groups can destabilize

Ideal Recrystallization Solvent Characteristics

1. The solvent should not chemically react with the compound. 2. The solvent should dissolve the compound when hot. 3. This same solvent should not dissolve the compound when cold. 4. The solvent should either dissolve the impurities at all temperatures or not dissolve impurities at all.

Lab #1 Pre-Lab Question #1: If you start with 1.98 grams of salicylic acid (138.12 g/mol), assuming excess of all other reactants, what is the theoretical yield, in grams (2 dec places), of acetylsalicylic acid (180.16 g/mol)?

2.58 g

Grignard reactions form a new C-C bond. In the case of aldehydes, the product is a ____ alcohol and in the case of ketones, the product is a ____ alcohol. An ester, on the other hand, reacts ________ with the grignard reagent to get a ____ alcohol.

2°; 3°; twice; 3° Note: know how this reaction works!

Lab #4 Discussion Worksheet Kinetic vs Thermodynamic Question #3, 4, & 5: 3. Which product favorite if kinetically driven? 4. Draw two contributing resonance structures following protonation of diene (see discussion questions). 5. From question 4, indicate what major product would be under low and high temperature conditions?

3. X1 4. basically have one as 1,2 and one as 1,4 5. low temperature product would be the 1,4 one and high temperature product would be the 1,2 one (pretty sure this needs fact checking)

Lab #2 Pre-Lab Question #1: Theoretically, for every one mole of NaBH4, ______ moles of an aldehyde can be reduced.

4

Borneol has a 1H NMR shift at ________ppm while Isoborneol has a 1H NMR shift at ________ppm.

4.00; 3.61

Lab #2 Pre-Lab Question #5: Jeanette isolated her product and used an NMR spectrometer to obtain an NMR spectrum. The signal for borneol at 4.00 ppm has an integration of 4.222 and the signal for isoborneol at 3.61 ppm has an integration of 4.321. What is the percentage of isoborneol (round to 2 decimal places)?

50.58% - % isoborneol = (integration of isoborneol / (integration of borneol + isoborneol)) x 100 - % isoborneol = (4.321/(4.222+4.321)) x 100 = 50.58% KNOW THIS!!!

At high temperatures, both paths are _________________ and the ___________ stable path dominates. A. reversible; more B. reversible; less C. irreversible; more D. irreversible; less

A

Borneol is the _______ (or ________) product while Isoborneol is the _______ (or _________) product. A. endo; minor; exo; major B. endo; major; exo; minor C. exo; minor; endo; major D. exo; major; endo; minor

A

Category I derivatives of carboxylic acids _________ a leaving group and often _________ resonance forms. A. have; have B. have; lack C. lack; have D. lack; lack

A

Lab #5 Pre-Lab Question #5: For a carbocation, electron donating groups ________ and electron withdrawing groups ________. A. stabilize, destabilize B. destabilize, destabilize C. destabilize, stabilize D. stabilize, stabilize

A

Lab #5 Pre-Lab Question #3: Sodium hypochlorite is considered an (choose multiple).... A. corrosive B. irritant C. reductant D. acid

A & B

Lab #5 Pre-Lab Question #4: If you come into contact with salicylamide, hydrochloric acid, sodium iodide, or sodium hypochlorite; you should (choose multiple)... A. notify your TA B. wash the affected area with running water for 15 minutes C. neutralize the chemical with its polar opposite D. deodorize the chemical

A & B

Lab #7 Pre-Lab Question #5: Which of the following derivatives of carboxylic acids have resonance forms (choose multiple)? A. amide B. anhydride C. ketone D. aldehyde

A & B

When isobutylene is combined with HBr, which of the following are possible intermediates (choose multiple)? A. a tertiary carbocation B. a primary carbocation C. a primary carbanion D. a secondary carbocation

A & B

Lab #7 Pre-Lab Question #4: Which of the following statements are true regarding carboxylic acids (choose multiple)? A. The oxygen in the carbonyl bond is more electronegative than the carbon. B. The oxygen in the O-H bond is acidic. C. The oxygen in the O-H bond is more electronegative than the hydrogen. D. The oxygen in the carbonyl bond is more electrophilic than the carbon.

A & C

Lab #4 Pre-Lab Question #2: At _______ temperature, ________ control is exerted (choose multiple). A. high, thermodynamic B. high, kinetic C. low, thermodynamic D. low, kinetic

A & D

What is a positive test result via the Iodoform Test?

A bright yellow precipitate, known as Iodoform, should form. This indicates that the compound is a methyl ketone.

Crossed Aldol Reaction

A chemical reaction in which an enol or enolate ion of one ketone or aldehyde reacts with the carbonyl group of a different aldehyde or ketone under basic or acidic conditions.

What is an enol?

A compound that contains "-en" which is an alkene and an "-ol" which is an alcohol.

How can you get an inconclusive Schiff's Test?

A faint color change can indicate an aromatic aldehyde or aliphatic ketone and can't distinguish between these two.

What is the significance of the Schiff's Test?

A qualitative test used to distinguish aliphatic aldehydes from aromatic aldehydes, aliphatic ketones, and aromatic ketones via a rapid color case.

What is the significance of the Tollens' Test?

A qualitative test used to identify aldehydes which can be oxidized to a carboxylic acid. It's mainly used to disinguish between aldehydes and ketones.

What is the significance of the Iodoform Test?

A qualitative test used to identify the presence of a methyl ketone or secondary alcohols that oxidize to methyl ketones.

Lab #3 Pre-Lab Question #5: Grignard reagents can react with which of the following categories of compounds to form alcohols (choose multiple)? A. ketones B. esters C. aldehydes D. alkanes

A, B, & C

Lab #9 Pre-Lab Question #3: The extent to which dyes are absorbed or adsorbed by fabrics is based on (choose multiple)...... A. ionic interactions B. hydrogen bonding interactions C. color flow interactions D. solubility interactions

A, B, & D

Lab #1 Pre-Lab Question #4: Which of the following apply to phosphoric acid (choose multiple)? A. Contact can severely burn eyes B. Wear gloves when handling C. Contact can severely burn skin D. Inhalation will irritate nose, mouth, and throat

A, B, and C

Based on Safety Case Study #2, which of the following recommend nitrile rubber gloves for skin protection (choose multiple)? A. Salicylic Acid B. Camphor C. Acetone D. Dichloromethane E. Sodium Borohydride

A, B, and E

Lab #9 Pre-Lab Question #4: Which of the following are naturally occuring fabrics (choose multiple)? A. Silk B. Nylon C. Wool D. Cotton

A, C, & D

Lab #1 Pre-Lab Question #2: Which of the following are compounds that are produced by living organisms (choose multiple)? A. Secondary metabolites B. Natural products C. Acetylsalicylic acid D. Primary metabolites

A, C, and D

Based on Safety Case Study #2, which of the following are both a physical and chemical mitigation (the others are just physical)? A. Hand-Washing B. Gloves C. Goggles D. Safety Shower E. Eyewash F. Fume Hoods G. Appropriate Clothing

A, D, and E

What is the ideal range for melting point for a product to be considering purified?

About 1-2°C max. A range above 2°C indicates that impurities are likely present in the product.

Based on Safety Case Study #5, how does acryloyl chloride chemically interact with humans?

Acryloyl chloride has the ability to interact with water or other organic compounds present in human tissues, which can lead to the formation of hydrochloric acid and other reactive species. This is because acryloyl chloride is a highly reactive compound due to chlorine being a good leaving group. In humans, water, alcohols, amino acids, proteins, and DNA all have the ability to react via nucleophilic attack reactions.

Category II derivatives of carboxylic acids tend to undergo which type of reactions?

Addition Reactions

How many hydrogen NMR peaks will there be in anisole? How about in the major product upon iodination? And in the minor product upon iodination?

Anisole: 4 1H NMR peaks (idk why the 3rd spectrum only has 3 unless I'm wrong) Major Product: 3 1H NMR peaks Minor Product: 4 1H NMR peaks

Aliphatic aldehydes will produce a practically _____________________ color change while ketones and aromatic aldehydes will produce the same color change at a ______________ rate. A. instantaneous; faster B. instantaneous; slower C. delayed; faster D. delayed; slower

B

At low temperatures, conjugated dienes tend to favor the ________ adduct whereas at high temperatures they tend to favor the ________ adduct. A. 1,4; 1,2 B. 1,2; 1,4 C. 1,4; 1,3 D. 1,2; 1,3

B

Based on Safety Case Study #4, the acrylation reaction requires what two components? A. 1° amine and acrylic acid B. 1° amine and acryloyl chloride C. 2° amine and acrylic acid D. 2° amine and acryloyl chloride E. 3° amine and acrylic acid F. 3° amine and acryloyl chloride

B

In the formation of an azo dye, a ____________ aryl amine is used to be converted into a _____________ salt which reacts with a _____________ compound to produce an azo dye. A. primary; ammonium; phenolic B. primary; diazonium; phenolic C. primary; diazonium; alkyl D. secondary; ammonium; phenolic E. secondary; ammonium; alkyl F. secondary; diazonium; alkyl G. tertiary; ammonium; phenolic H. tertiary; diazonium; phenolic I. tertiary; ammonium; alkyl

B

In the organohalide, the carbon is __________________ while in the Grignard reagent the carbon is __________________. A. electrophilic; electrophilic B. electrophilic; nucleophilic C. nucleophilic; electrophilic D. nucleophilic; nucleophilic

B

Indigo is notorious for its vibrant colors primarily due to? A. ring structure B. pi conjugation C. carbonyl group D. hyperconjugation

B

Lab #5 Pre-Lab Question #2: The prevalence of goiters in certain regions was linked to..... A. a lack of electrophiles B. iodine deficiency C. too many aromatic compounds in the water D. an industrial factory that aerosolized chlorine

B

Lab #8 Pre-Lab Question #2: TPCP is a colored compound. What is the chemical basis for the color? A. carbonyl functional group B. conjugation C. cyclic structure D. aromaticity

B

Lab #8 Pre-Lab Question #5: What is another name for an aldol product? A. alpha ketone B. beta-hydroxycarbonyl C. beta-halocarbonyl D. alcohol

B

Meta directors _________ only deactivating. Furthermore, these directors are typically _____________ ___________________ _____________ (________). A. are; Electron Donating Groups (EDGs) B. are; Electron Withdrawing Groups (EWGs) C. aren't; Electron Donating Groups (EDGs) D. aren't; Electron Withdrawing Groups (EWGs)

B

The indigo synthesis is a type of ___________________ reaction. A. Addition B. Condensation C. Elimination D. Oxidation E. Reduction

B

Via the Ferric Chloride Test, Salicylic Acid ________ form a deep ___________ color while acetylsalicylic acid _______ form this color. A. will; yellow; won't B. will; purple; won't C. won't; yellow; will D. won't; purple; will

B

Lab #8 Pre-Lab Question #4: Which of the following types of compounds typically readily form resonance structures (choose multiple)? A. alcohols B. enols C. aromatic rings D. alkyl halides

B & C

Lab #9 Pre-Lab Question #2: In order to be an organic dye, a chemical compound should (choose multiple)....... A. redirect light energy into a specific wavelength B. contain conjugated pi bonds C. absorb a wavelength of light D. contain a ring structure

B & C

Lab #3 Pre-Lab Question #1: Which of the following techniques will you use during the Synthesis of Benzoic Acid Derivatives Experiment (choose multiple)? A. recrystallization B. vacuum filtration C. TLC D. extraction

B & D

Lab #8 Pre-Lab Question #3: What functional groups must be present in an enol (choose multiple)? A. ketone B. alcohol C. halide D. alkene

B & D

Lab #4 Pre-Lab Question #1: Which of the following are methods of calculating molecular properties (choose multiple)? A. balls on a string B. ab initio C. semi-empirical D. molecular mechanics

B, C, & D

Molecular mechanics can be used to calculate (choose multiple): A. the melting point of a molecule B. heat of formation of a compound C. dipole moment of a molecule D. molecular geometry

B, C, & D

Based on Safety Case Study #2, which of the following are preventive safety measures (the others are responsive)? A. Hand-Washing B. Gloves C. Goggles D. Safety Shower E. Eyewash F. Fume Hoods G. Appropriate Clothing

B, C, F, and G

At low temperatures, both paths are _________________ and the ___________ path dominates. A. reversible; faster B. reversible; slower C. irreversible; faster D. irreversible; slower

C

Azo dyes account for ________ of all commercial dyes (choose best answer). A. >40% B. >50% C. >60% D. >70%

C

Based on Safety Case Study #4, where should acryloyl chloride be disposed of? A. sink B. solid waste container in fume hood C. liquid waste container in fume hood D. take it home with you

C

In Electrophilic Aromatic Substitution (EAS) reactions, the overall energy of the system is ________________ and the carbocation intermediate is ___________________ via resonance. A. increased; stabilized B. increased; destabilized C. decreased; stabilized D. decreased; destabilized

C

Indigo is water ___________ and thus needs to be converted into ____________________ via ______________ to form a water ______________ compound. [Blank 2] can then proceed via ________________ to get back indigo. A. soluble; Leucoindigo; reduction; insoluble; oxidation B. soluble; Leucoindigo; oxidation; insoluble; reduction C. insoluble; Leucoindigo; reduction; soluble; oxidation D. insoluble; Leucoindigo; oxidation; soluble; reduction E. soluble; Leucoindigo; reduction; soluble; oxidation F. insoluble; Leucoindigo; reduction; insoluble; oxidation G. insoluble; Indigofera; oxidation; soluble; reduction H. insoluble; Indigofera; reduction; soluble; oxidation

C

Lab #3 Pre-Lab Question #2: Which of the following is another term for a Grignard reagent? A. organolithium reagent B. organosodium reagent C. organomagnesium reagent D. organomercury reagent

C

Lab #3 Pre-Lab Question #3: Regarding the polarity of the C-X bond in an organohalide, the carbon has a partial _______ charge, and the halide has a partial ______ charge. A. negative, positive B. negative, negative C. positive, negative D. positive, positive

C

Ortho and para directors ________ only activating. Furthermore, these directors are typically _____________ ___________________ _____________ (________). A. are; Electron Donating Groups (EDGs) B. are; Electron Withdrawing Groups (EWGs) C. aren't; Electron Donating Groups (EDGs) D. aren't; Electron Withdrawing Groups (EWGs)

C

In the Iodination of Salicylamide, where will the iodine be placed upon reaction (consider steric hinderance)? A. at the position ortho to the -OH (meta to -CONH2) B. at the position meta to the -OH (para to -CONH2) C. at the position para to the -OH (meta to -CONH2) D. at the position ortho to the -CONH2 (meta to -OH)

C Note: C will form as the major product but A also forms as the minor product.

What is the substitution pattern of the final major product in the Iodination of Salicylamide reaction? A. 1,2-disubstituted B. 1,2,3-trisubstituted C. 1,2,4-trisubstituted

C Note: This is due to a peak on the IR between 800-850 cm^-1.

In Fischer Esterification, which two compounds are needs to form an ester? A. aldehyde and alcohol B. ketone and alcohol C. carboxylic acid and alcohol D. aldehyde and ketone E. Actually requires four compounds

C Note: know the reaction and curved arrow mechanism!

Lab #6 Pre-Lab Question #5: Which of the following are potential unknown aldehydes or ketones for the Reactions of Aldehydes and Ketones experiment? A. benzaldehyde B. benzoic acid C. cyclopentanone D. heptan-2-one

C & D

Lab #3 Pre-Lab Question #4: If you get hydrochloric acid or sodium hydroxide on your skin (choose multiple)... A. wash the affected area with running water for 15 minutes B. notify your TA C. shake it off (Taylor's Version) D. rub some dirt on it

C (jkjk though Taylor is goated) Correct Answer: A & B

In a 1,2,4-trisubstituted substitution pattern for the Iodination of Salicylamide reaction, you would observe ___ singlet(s), ___ doublet(s), and ___ triplet(s). A. 1; 1; 1 B. 1; 2; 0 C. 2; 1; 0 D. 2; 2; 2 E. 2; 2; 1 F. 1; 0; 1 G. 1; 2; 1 F. 25; 36; 49

C (look at lab final exam review video)

In the crossed aldol reaction of dibenzyl ketone with benzil, which reactant can be enolized and which cannot?

Can: dibenzyl ketone Cannot: benzil

Lab #4 Discussion Worksheet #2 and #5: Explain the order of stability of carbocation intermediates.

Carbocation stability generally dependent on the degree in which 3° > 2° > 1°. However, delta E gives more insight....(sort of). "Missing Resonance Delocalization" um Intermediate B is most stable, followed by C and then A because intermediate B and C have very electronegative atoms attached at the end of their parent chain, acting as a stabilizing factors. All three are secondary and allylic though.

Lab #2 Pre-Lab Question #2: Order based upon the oxidation state of carbon from most to least oxidized. Ketone Saturated Hydrocarbon Carboxylic Acid Alcohol

Carboxylic Acid > Ketone > Alcohol > Saturated Hydrocarbon

Category II derivatives of carboxylic acids _________ a leaving group and often _________ resonance forms. A. have; have B. have; lack C. lack; have D. lack; lack

D

C-O reduction can be accomplished using Sodium Borohydride, which is a _________ reducing agents, specifically dealing with reducing only _______________ and ______________. A. mild; carbonyls; esters B. mild; carboxylic acids; ketones C. mild; esters; aldehydes D. mild; ketones; carbonyls E. mild; aldehydes; ketones F. strong; carbonyls; esters G. strong; carboxylic acids; ketones H. strong; esters; aldehydes I. strong; ketones; carbonyls J. strong; aldehydes; ketones

E

The reactivity of Category I compounds is defined by the ____________ of the C-____ double bond. A. hybridization; N B. hybridization; O C. hybridization; X D. polarity; N E. polarity; O F. polarity; X

E

If there is a tie in the degree of the carbocation, what is taken into acccount?

Electronegativity and the resonance/inductive effect

Lab #5: Iodination of Salicylamide

Fun times!

In the reaction of salicylic acid with acetic anhydride, the reagent used is ____________ and the products formed are _________________ _______ (AKA ___________) and __________ ______.

H3PO4; acetylsalicylic acid; aspirin; acetic acid

Lab #5 Pre-Lab Question #1: Typically, in order to perform an electrophilic aromatic substitution, you need the two reagents? A. an electrophile and an acid B. an electrophile and a base C. a nucleophile and a base D. a nucleophile and an acid

I got this wrong.....I put A (please lmk if you know the answer)

Lab #4 Discussion Worksheet #1 and #4: Draw the reaction coordinate diagram......*sobs in background*

IDK sadly

Lab #6 Pre-Lab Question #4: Which of the following forms of analysis are based on a physical property of your unknown? A. IR spectroscopy B. distillation C. 1H NMR D. Tollens' Test

Idk I got this wrong.....I put A and B (please lmk if you know).

How can you get an inconclusive Iodoform Test?

If the brown color upon addition of the iodine-potassium iodide solution stays discharged or forms a light hue of coloration not indicative of the yellow precipitate. Usually negative test result but not always.

How can you get an inconclusive Tollens' Test?

If there are contaminants or substances preventing the reaction from going to completion.

Where does the acidic proton come from in a grignard reaction?

It comes from the acidic workup step, which involves the addition of water or dilute acid after the Grignard reaction has occurred.

Lab #8: Aldol Condensation

Keep it up!

General Info

Know how to interpret IR, 1H NMR, and 13C NMR (hard to incorporate that into a quizlet)!

Lab #9: Preparation of Azo Dyes

Last lab woohoo!

Lab #6: Reactions of Aldehydes and Ketones

Let's keep it going!

Lab #4: Molecular Modeling

Let's keep up the good work!

Lab #8 Discussion Questions #2: Provide the aldol product and enone (dehydration) product of self-aldol condensation reaction of acetone.

Look at discussion questions! Basically, line up the CH3 of one reactant and O of the other and perform a "snip" that creates a bond. Aldol product contains an OH while the enone product dehydrates to form a double bond. (mid explanation)

Lab #5 Discussion Questions #1: predict the major product for the following iodination reactions. Be sure to account for steric influence. a-c) look at structures in the discussion questions

Look at discussion questions! a) "I" added ortho to -CH3 and meta to -NO2 b) "I" added ortho to one -Cl and para to the other -Cl c) "I" added ortho to one -CH3 and para to the -NH2 (meta to the other -CH3 but that's not important)

Lab #5 Discussion Questions #2: Consider the reaction. (look at discussion questions) a) Circle the major product. b) Predict the number of peaks expected in the 13C spectrum of anisole. c) Match the structure with the spectrum.

Look at discussion questions! a) Major product has "I" added para to -OCH3 b) 5 peaks expected c) Anisole --> 3rd spectrum Major Product --> 1st spectrum Minor Product --> 2nd spectrum

Lab #1 Discussion Questions #1: Provide Curved Arrow Mechanism for Preparation of Aspirin (Acetylation of Salicylic Acid). --> I can't do this in Quizlet

Look at discussion questions!!!

Lab #7 Discussion Questions #1: Provide the full curved-arrow mechanism for the Fischer esterification shown below. (Review Discussion Questions)

Look at discussion questions!!!

Lab #8 Discussion Questions #1: Provide the curved-arrow mechanism for the second aldol condensation reaction en route to TPCP. --> can't on quizlet

Look at discussion questions!!!

Lab #9 Discussion Questions #2: Provide a reasonable curved-arrow mechanism (including resonance arrows) for this transformation of NaNO2 to NO+ and then to a benzendiazonium ion. --> can't do this on quizlet

Look at discussion questions!!!

Lab #9 Discussion Questions #1: Predict the structure of azo dyes C1-C3.

Look at discussion questions!!! For all three, where the -OH is the N2+ (which will become N=N) from the starting material wants to connect to the ortho or para (if ortho is occupied) position to it (sort of).

In the Iodination of Salicylamide, the reagents used are _________ and NaOCl dissolved in EtOH.

NaI

A carboxylic acid would have key functional groups and peaks where on an IR spectrum and NMR spectra? (use the charts)

OH: about 3000 cm^-1 Carbonyl: about 1680 cm^-1 1H NMR: 10-13 ppm 13C NMR: 170-180 ppm

Redox Reactions

Oxidation is loss of electron density on carbon. Reduction is gain of electron density on carbon. "OIL RIG"

________________ can cause the formation of C-O, C-N, and C-X bonds while _______________ causes the cleavage of these bonds.

Oxidation; Reduction

In Acid Chloride Ammonolysis, which two reactants are used and what are the products?

Reactants: Acid Chloride and Ammonium Hydroxide Products: Amide, HCl, and Water

In Acid Chloride Hydrolysis, which two reactants are used and what are the products?

Reactants: Acid Chloride and Water Products: Carboxylic Acid and HCl

Energy Diagrams (see review video and discussion worksheet) - Know Enthalpy Change & Activation Energy and be able to Draw with Intermediates (I'm not good at this....)

Show energy changes during a reaction. - Enthalpy Changes: change in energy between reactant and product --> determines thermodynamics of reaction - Activation Energy: amount of energy needed to transition between reactant to products --> determines kinetics of reaction

Based on Safety Case Study #2, which of the following are hazards to the skin, which to the eye/face, and which is an inhalation hazard? A. Hand-Washing B. Gloves C. Goggles D. Safety Shower E. Eyewash F. Fume Hoods G. Appropriate Clothing

Skin: A, B, D, G Eye/Face: C, E Inhalation: F

Category I derivatives of carboxylic acids tend to undergo which type of reactions?

Substitution Reactions

Order the carbocations based on stability from most to least stable. Secondary Methyl Tertiary Primary

Tertiary > Secondary > Primary > Methyl

In a positive Schiff's Test, upon reaction of the Schiff's reagent with the unknown compound, what should the result be?

The color should change almost instantaneously to a deep wine-purple color (or another immediate and vivid color change). This would indicate the presence of an aliphatic aldehyde.

Based on Safety Case Study #5, how did the acryloyl chloride come into contact with the student? Name at least two of the mistakes that were made.

The acryloyl chloride came into contact with the student because the contents of the beaker overflowed out of the beaker due to bumping and the student wasn't following the appropriate personal protective equipment guidelines. The first mistake was that the student wasn't wearing a helmet and was incorrectly wearing the N-90 mask, exposing the student to more risk. The second mistake was that the student left the fume hood partially open while the contents of the beaker were heating, allowing dangerous vapors to be expelled more readily.

Based on Safety Case Study #5, what is the reasoning for spreading ammonia around the top of the bottle containing acryloyl chloride? How does this occur?

The ammonia is sprinkled around the acryoyl chloride bottle in order to prevent dangerous fumes and vapors from the acryloyl chloride solution from quickly spreading to the environment, thus neutralizing the effects of acryloyl chloride vapors.

Based on Safety Case Study #2, why would the composition of the gloves make a difference?

The composition of the nitrile gloves would make it less resistant to solvation or degradation by a liquid solvent. This is beneficial for the compounds in the previous question since they are solid at room temperature.

Lab #4 Discussion Worksheet #3: The delta E of molecule F stands out from the other values. Does this mean F is the most or least stable carbocation? Why?

The delta E of molecule F is higher than the delta E of the other molecules. This means that F is the least stable carbocation. This is further demonstrated because molecule F is the only structure with a primary carbocation. Also, F is the least stable because the cation is not delocalized.

What is a positive test result via the Tollens' Test?

The formation of a silver mirror (or the formation of a black precipitate if test tube is contaminated). This would indicate the compound is an aldehyde.

Based on Safety Case Study #5, what is the biggest difference between acryloyl chloride and benzoyl chloride in terms of how it can come into contact with living organisms (humans)?

The main difference between acryloyl chloride and benzoyl chloride in terms of contact with living organisms is based on their structure and reactivity. Acryloyl chloride contains a vinyl group adjacent to a carbonyl whereas benzoyl chloride contains a phenyl group, thus making acryloyl chloride more reactive than benzoyl chloride. Furthermore, due to the benzene ring, benzoyl chloride is more likely to participate in electrophilic aromatic substitution reactions whereas acryloyl chloride has the ability to undergo addition reactions due to the presence of the carbon-carbon double bond. Note: this might be wrong

True or False: The products of the borohydride reduction of camphor contain diastereotopic protons.

True

Lab #6 Pre-Lab Question #3: Match the positive test result with the qualitative test. Tollens' Test Iodoform Test Schiff's Test Yellow Precipitate Wine-Colored Solution Silver Mirror

Tollens' Test --> Silver Mirror Iodoform Test --> Yellow Precipitate Schiff's Test --> Wine-Colored Solution

An enol can have multiple resonance forms. True or False.

True

Based on Safety Case Study #4, acryoyl chloride is a highly flammable liquid and vapor that can cause sever skin burns and eye damage. True or False.

True

Lab #1 Pre-Lab Question #3: For the Ferric Chloride Test, the deeper the color produced, the more salicylic acid. True or False.

True

Lab #2 Pre-Lab Question #4: Hot glass looks the same as cold glass. True or False.

True

Lab #5 Pre-Lab Question #6: Aromatic compounds are considered toxic. True or False.

True

Lab #6 Pre-Lab Question #2: A positive result from the Iodoform Test indicates the presence of a methyl ketone. True or False.

True

Lab #7 Pre-Lab Question #1: Concentrated sulfuric acid will produce serious burns on contact with skin. True or False.

True

Lab #7 Pre-Lab Question #3: When you invert a Pasteur pipet, the contents of the pipet will go into the bulb. That presents a safety hazard and contamination risk for anyone that uses the bulb afterwards. True or False.

True

Lab #8 Pre-Lab Question #1: Heating mantles should be plugged into variacs and then the variac has a dial to set the amount of power to deliver to the heating mantle. True or False.

True

Lab #9 Pre-Lab Question #1: Since you will be working with dyes, you shouldn't wear white clothing or at least clothing that you do not want to accidentally dye. True or False.

True

Based on Safety Case Study #4, when dealing with acryloyl chloride it is recommended to wear nitrile gloves, a helmet, and an N-90 mask. True or False. If the answer is True, what one other item of recommended PPE is necessary?

True Apron covering entire body

Lab #7: Derivatives of Carboxylic Acids

We've made it this far let's keep going!

Lab #2: Borohydride Reduction of Camphor

Woohoo!

Lab #4 Discussion Worksheet Kinetic vs Thermodynamic Question #1: Draw and rank the products from most thermodynamically stable to least thermodynamically stable. Which is the thermodynamic control product?

X2 > X1 > Y1 (see discussion questions) Thermodynamic Control Product: Y1 Rules: 1. Zaitsev's Rule 2. Carbocation Stability

Good Luck everyone!

Y'all will do amazing!

Lab #1: Preparation of Aspirin

Yay! Let's begin!

Lab #3: Synthesis of a Benzoic Acid Derivative

Yippee!

Lab #1 Discussion Questions #2: A student records a mass of 1.23 g of salicylic acid. Following the final filtration, 1.72 g of crude aspirin is isolated. a) Calculate Theoretical Yield. b) Calculate Percent Yield. c) Is the percent yield in part b accurate?

a) 1.60 g - 1.23 g x (1 mol/138.12 g) x (180.16 g/1 mol) = 1.60 g b) 108% - actual/theoretical x 100 = 1.72/1.60 x 100 = 108% c) No, the percent yield over 100% signifies that there are impurities present. This is likely due to lot of excess water or some of reactant being left over.

Lab #8 Discussion Questions #3: Provide the major product for the following crossed aldol condensation reactions. Assume dehydration occurs. a) Look at structures in DQs b) Look at structures in DQs c) Look at structures in DQs

a) Look at DQs b) Look at DQs c) Look at DQs Note: the double bond formed in the enone product is always at the position alpha to the carbonyl carbon

Lab #7 Discussion Questions #2: Consider the Fischer Esterification Reactions. a) Provide Missing Starting Material. b) Match the products to the 1H NMR spectra provided.

a) Look at discussion questions but wherever there is an CH3-O bond or either side of the cyclic O in the product is where there is an OH in the starting material (might not be explaining this right) b) Product A --> 2nd spectrum Product B --> 3rd spectrum Product C --> 1st spectrum

Lab #2 Discussion Questions #1: NaBH4 reacts slowly with water to generate H2 gas. a) Provide the curved-arrow mechanism for this transformation for 1 equivalent of H2. b) Do you expect aqueous NaBH4 solution to be acidic, basic, or neutral?

a) Look at discussion questions or ask me b) basic (due to hydrolysis of BH4- ions with H2O)

Lab #2 Discussion Questions #3: See figure of (+)-camphor in discussion questions. a) Is the bridgehead carbon bearing a methyl group (adjacent to the carbonyl) an R or S stereocenter? b) Is the bridgehead carbon bearing a hydrogen an R or S stereocenter?

a) R stereocenter b) R stereocenter

Lab #2 Discussion Questions #2: You run the borohydride reduction of camphor. Following isolation of your product, you obtain spectral data. a) Your IR spectrum shows significant absorption bands at 1740 cm^-1 and 3400 cm^-1. What can you deduce from this data? b) Your 1H NMR spectrum shows a broad peak at 1.56. What is it? How can you adjust your protocol to ensure that peak is not present in the spectrum of your final purified product?

a) There is a carbonyl (C=O) stretch and an O-H stretch, likely indicating an alcohol, present in the final product. b) The peak at 1.56 is likely residual water from the recrystallization step, signifying insufficient drying. The protocol could be adjusted to better dry the product prior to obtaining a 1H NMR spectrum.

In an Aldol Condensation reaction, there is an addition of an enol or enolate to a __________________ or _______________.

aldehyde; ketone

Schiff's test primarily distinguishes between _______________ and _______________ aldehydes.

aliphatic; aromatic

Based on Safety Case Study #3, what subcategories can the liquid waste streams be split into (for helping define the nature of chemicals dissolved in solution)?

aqueous acidic waste, aqueous basic waste, aqueous oxidizing waste, and aqueous heavy metal waste

Based on Safety Case Study #3, what are the three main types of liquid waste streams typical in organic chemistry labs?

aqueous, non-halogenated organic, and halogenated organic

During the borohydride reduction of camphor, the reaction breaks down camphor into ____________ and _____________ products.

borneol; isoborneol

In the Benzoic Acid Derivative reaction, the CO2 is converted into upon reaction with the grignard reagent and water?

carboxylic acid

What is regiochemistry and which carbocation product will dominate (major product)? What is the rule for this?

describes where the reaction takes place and the more stable carbocation leads to the major product Markovnikov's Rule: more stable intermediate --> major product

Based on Safety Case Study #3, what is the first step in segregating chemical waste?

determining whether it is hazardous to the environment and/or what it might react with as it enters local sewage

In the crossed aldol reaction of dibenzyl ketone with benzil, which reactant has alpha protons?

dibenzyl ketone

What are the byproducts in the baeyer-dewsen synthesis?

indigo and acetic acid

Grignard reagents are both _______________ and ________. The magnesium gets a partial ___ charge and the carbon of the R group gets a partial ___ charge.

nucleophilic; basic; +; -

Based on the structure of salicylamide, what ortho-/para- director and what meta- director does it have?

o/p: -OH group meta: -CONH2 group

Via the Grignard reaction, the final product will always be an _________________ (organic/inorganic) compound.

organic

Ferric Chloride Test

qualitatively determines the presence of a phenol functional group and forms a highly colored iron-phenol complex if present

In a positive Iodoform Test, a bright ____________ precipitate, known as ________________ is formed.

yellow; Iodoform