Review for Finals
From the given compounds below, which will not form a silver mirror in Tollen’s Test but will give a positive result in Iodoform Test? • • • •
3-hexanol 3-pentanone 2-methylcyclohexanal phenylethanone
From the given compounds below, which will not form a silver mirror in Tollen’s Test but will give a positive result in Iodoform Test? • • • •
3-hexanol 3-pentanone 2-methylcyclohexanal phenylethanone
Why was Ingrain dyeing employed in the Sudan I experiment?
• Fully formed Sudan I is too large to anchor itself on the cloth • The cloth and Sudan I have the same intermolecular forces of attraction • Sudan I is able to form chemical interaction with the cloth via salt linkages • Sudan I can bond well with the functional groups present in the cloth
Why was Ingrain dyeing employed in the Sudan I experiment?
• Fully formed Sudan I is too large to anchor itself on the cloth • The cloth and Sudan I have the same intermolecular forces of attraction • Sudan I is able to form chemical interaction with the cloth via salt linkages • Sudan I can bond well with the functional groups present in the cloth
Which will react the fastest in Seliwanoff’s Test? • • • •
Fructose Glucose Galactose Starch
Which will react the fastest in Seliwanoff’s Test? • • • •
Fructose Glucose Galactose Starch
Which of the following cannot be used as a starting material for soap making? • • • •
Cooking oil Mayonnaise Glycerol Lye
Which of the following cannot be used as a starting material for soap making? • • • •
Cooking oil Mayonnaise Glycerol Lye
Which substituent enhances the acidity of carboxylic acids when bonded directly to the acyl carbon? • • • •
-CH2CH3 -OCH3 -OH -NO2
Which substituent enhances the acidity of carboxylic acids when bonded directly to the acyl carbon? • • • •
-CH2CH3 -OCH3 -OH -NO2
Hinsberg test for Nmethylethanamine will yield a product that is ___ in excess NaOH and ___ in 5% HCl acid. • • • •
Soluble, insoluble Soluble, soluble Insoluble, insoluble Insoluble, soluble
Hinsberg test for Nmethylethanamine will yield a product that is ___ in excess NaOH and ___ in 5% HCl acid. • • • •
Soluble, insoluble Soluble, soluble Insoluble, insoluble Insoluble, soluble
Which among the following combination (compound-reagentresult) is correct? • Acetone - Ag(NH3)2+ – silver mirror • Propanal – Na citrate, NaHCO3 and CuSO4 in water – brick red ppt • Formalin – Schiff’s reagent – light pink color • Cylopentanone – I2 in KI and NaOH – yellow ppt
Which among the following combination (compound-reagentresult) is correct? • Acetone - Ag(NH3)2+ – silver mirror • Propanal – Na citrate, NaHCO3 and CuSO4 in water – brick red ppt • Formalin – Schiff’s reagent – light pink color • Cylopentanone – I2 in KI and NaOH – yellow ppt
Which of the following is not a property of soap?
• Soaps have hydrophobic and hydrophilic parts • Soaps are the result of the reaction between glucose and potassium hydroxide • The hydrophobic part of soap is its nonpolar tail • The nonpolar part causes the formation of micelles
Which of the following is not a property of soap?
• Soaps have hydrophobic and hydrophilic parts • Soaps are the result of the reaction between glucose and potassium hydroxide • The hydrophobic part of soap is its nonpolar tail • The nonpolar part causes the formation of micelles
Esters form a magenta colored complex with FeCl3 after treatment with ______. • • • •
NH4OH with alcoholic KOH Alcoholic NH4Cl and alcoholic KOH Neutral NH4Cl and alcoholic KOH Alcoholic NH2OH·HCl and Alcoholic KOH
Esters form a magenta colored complex with FeCl3 after treatment with ______. • • • •
NH4OH with alcoholic KOH Alcoholic NH4Cl and alcoholic KOH Neutral NH4Cl and alcoholic KOH Alcoholic NH2OH·HCl and Alcoholic KOH
Which of the following is formed upon addition of benzensulfonyl chloride and NaOH with aniline? • • • •
Sulfonamine Sulfonamide Sulfoxamine Sulfonylamide
Which of the following is formed upon addition of benzensulfonyl chloride and NaOH with aniline? • • • •
Sulfonamine Sulfonamide Sulfoxamine Sulfonylamide
Which of the following acyl compound-alcohol pair produces ester in the least amount? • • • •
Methanoic anhydride and ethanol Acetic acid and butanol Sodium butanoate and propanol Ethanamide and 2-propanol
Which of the following acyl compound-alcohol pair produces ester in the least amount? • • • •
Methanoic anhydride and ethanol Acetic acid and butanol Sodium butanoate and propanol Ethanamide and 2-propanol
Ribonucleic Acid, RNA, contains the sugar ribose. What test can be used to detect its presence in a sample of RNA? • • • •
Hydroxamic Acid Test Bial’s Test Ninhydrin Test Hinsberg Test
Ribonucleic Acid, RNA, contains the sugar ribose. What test can be used to detect its presence in a sample of RNA? • • • •
Hydroxamic Acid Test Bial’s Test Ninhydrin Test Hinsberg Test
Which type of amine cannot be characterized using Hinsberg’s method? • • • •
Primary Amine Secondary Amine Tertiary Amine Amphoteric Amine
Which type of amine cannot be characterized using Hinsberg’s method? • • • •
Primary Amine Secondary Amine Tertiary Amine Amphoteric Amine
A soap molecule is a/an • • • •
Ester Carboxylic acid Amide Carboxylate Salt
A soap molecule is a/an • • • •
Ester Carboxylic acid Amide Carboxylate Salt
The product of the hydrolysis of this acid derivative changes a litmus paper from red to blue and produces a distinct sour smell. What could be this compound?
The product of the hydrolysis of this acid derivative changes a litmus paper from red to blue and produces a distinct sour smell. What could be this compound?
Which of the following would prevent the formation of side products in the synthesis of Sudan I?
• Preparing phenyldiazonium chloride solution in a acidic medium • Recrystallization of the product • Preparing β-naphthol solution in acidic medium • None of the above
Which of the following would prevent the formation of side products in the synthesis of Sudan I?
• Preparing phenyldiazonium chloride solution in a acidic medium • Recrystallization of the product • Preparing β-naphthol solution in acidic medium • None of the above
What test/reagent may be used to confirm the product of methanol and benzoic acid upon refluxing with H2SO4 ? • • • •
Friedel-Craft’s alkylation 5% NaHCO3 Lucas Test Hydroxamic Acid Test
What test/reagent may be used to confirm the product of methanol and benzoic acid upon refluxing with H2SO4 ? • • • •
Friedel-Craft’s alkylation 5% NaHCO3 Lucas Test Hydroxamic Acid Test
3-phenylbutanal will give positive result on the following tests except: • • • •
Reaction with 2,4-DNPH Schiff’s test Iodoform test Benedict’s test
3-phenylbutanal will give positive result on the following tests except: • • • •
Reaction with 2,4-DNPH Schiff’s test Iodoform test Benedict’s test
Modified True or False 1. Seliwanoff’s test is a test for RNA. 2. Compounds that yield the same osazone are known as enantiomers. 3. Soap molecules tend to form micelles due to their hydrophobic heads.
Modified True or False 1. Bial’s Test is a test for RNA. 2. Compounds that yield the same osazone are known as epimers. 3. Soap molecules tend to form micelles due to their hydrophobic tails.
4. Reaction of acetic acid with FeCl3 gives a flesh colored precipitate. 5. Refluxing purifies the synthesized ester through removal of excess water by evaporation. 6. In the synthesis of ester, H2SO4 acts as the catalyst by making the C=O of the carboxylic acid a good leaving group. 7. 2-pentanol and acetone can’t be differentiated using Iodoform test.
4. Reaction of acetic acid with FeCl3 gives a Red solution/red complex. 5. Distillation purifies the synthesized ester through removal of excess water by evaporation. 6. In the synthesis of ester, H2SO4 acts as the catalyst by making the O-H of the carboxylic acid a good leaving group. 7. 2-pentanol and acetone can’t be differentiated using Iodoform test. TRUE!
8. The coupling reagent should contain strongly electron donating groups to facilitate the coupling reaction in the synthesis of diazo compounds. 9. Diazotization requires primary alkylamines to react with HONO to produce the diazonium salt. 10. Base hydrolysis of primary amides yields a vapor that turns litmus paper red to blue.
8. The coupling reagent should contain strongly electron donating groups to facilitate the coupling reaction in the synthesis of diazo compounds. TRUE 9. Diazotization requires primary aromatic amines to react with HONO to produce the diazonium salt. 10. Base hydrolysis of primary amides yields a vapor that turns litmus paper red to blue. TRUE
11. Cyclobutanol produces a yellow orange precipitate with 2,4-DNPH. 12. In diazotization, sodium nitrite is converted to HNO2, the primary diazotization reagent. 13. Hydrolysis of polysaccharides takes time due to several double bonds that need to be broken. 14. Given 1 mole of triglyceride, three moles of KOH is necessary for saponification.
11. Cyclobutanol produces a yellow orange solution with 2,4-DNPH. 12. In diazotization, sodium nitrite is converted to HNO2, the primary diazotization reagent. TRUE 13. Hydrolysis of polysaccharides takes time due to several glycosodic bonds that need to be broken. 14. Given 1 mole of triglyceride, three moles of KOH is necessary for saponification. TRUE
Azo DYES!!! Give the amine and coupling compound.
• Eriochrome Black T- complexometric indicator
Amine
Coupling agent
Azo DYES!!! Give the amine and coupling compound. • Fast Yellow AB- food dye (harmful)
• AMINE
• Coupling Agent
Azo DYES!!! Give the amine and coupling compound. • Alizarin Yellow R – pH indicator
• Amine
• Coupling Agent
Azo DYES!!! From the reagents, give the Azo Dye!
• Citrus Red 2 – carcinogenic dye used on some skin of oranges
Azo DYES!!! From the reagents, give the Azo Dye!
• Methyl Red – used as pH indicator
CHEMICAL Differentiation! Give test/reagent and visible result that would differentiate the compounds.
CHEMICAL Differentiation! Give test/reagent and visible result that would differentiate the compounds.
• FeCl3 – colored complex • Lucas Test layer
CHEMICAL Differentiation! Give test/reagent and visible result that would differentiate the compounds.
CHEMICAL Differentiation! Give test/reagent and visible result that would differentiate the compounds.
• • • • • •
5% NaHCO3 - effervescence 2,4-DNPH – yellow orange crystals Tollen’s Test – silver mirror Benedict’s Test – brick red ppt Schiff’s Test – purple/violet complex pH – acidic or solubility in NaOH
CHEMICAL Differentiation! Give test/reagent and visible result that would differentiate the compounds.
CHEMICAL Differentiation! Give test/reagent and visible result that would differentiate the compounds.
• Hinsberg Test – Dense layer/residue
• Test for Nitrogen – Blue green solution
CHEMICAL Differentiation! Give test/reagent and visible result that would differentiate the compounds.
• Iodoform – yellow ppt • Hinsberg Test residue • Schiff’s Test – violet complex • T-butyl chloride, AlCl3 – orange crystal
Unknown Analysis: Draw the Structure of the Unknown Compound • Resveratrol – a polyphenol found in the skin of red grapes, with formula C14H12O3 Test/Reagent
Observation/ Result
Inference
Ignition test
(1)
Aromatic Ring present
Conc. H2SO4
soluble
(2)
(3)
White to yellow/orange crystals
Aromatic ring is present
KMnO4
(4)
Alkene part is present
(5)
Yellow solution, negative
Saturated part is absent
(6)
Highly colored complex
3,5-disubstituted phenol is present Para-substituted phenol is also present
2,4-DNPH
Yellow solution, no ppt
(7)
5% NaHCO3
NVR
(8)
(9)
negative
Ester group is absent
Unknown Analysis: Draw the Structure of the Unknown Compound • Resveratrol – a polyphenol found in the skin of red grapes, with formula C14H12O3 Test/Reagent
Observation/ Result
Inference
Ignition test
Sooty Flame
Aromatic Ring present
Conc. H2SO4
soluble
Solubility class: N
AlCl3, t-butyl chloride
White to yellow/orange crystals
Aromatic ring is present
KMnO4
Decolorization, brown ppt
Alkene part is present
Br2 in water, Light
Yellow solution, negative
Saturated part is absent
FeCl3
Highly colored complex
3,5-disubstituted phenol is present Para-substituted phenol is also present
2,4-DNPH
Yellow solution, no ppt
No carbonyl group
5% NaHCO3
NVR
No carboxylic acid part
Hydroxyamic Test
negative
Ester group is absent
Unknown Analysis: Draw the Structure of the Unknown Compound • Resveratrol – a polyphenol found in the skin of red grapes, with formula C14H12O3
Unknown Analysis: Draw the Structure of the Unknown Compound • Unknown compound with formula: C8H9O2N • Compound is para substituted Test/Reagent
Observation
Interference
5% HCl
NVR
(1)
(2)
Yellow soln
Not an aldehyde or ketone
5% NaHCO3
NVR
(3)
Benzenesulfonyl chloride
No residue
(4)
FeCl3
(5)
Phenol group present
Hydroxamic acid test
(6)
No ester group present
Unknown Analysis: Draw the Structure of the Unknown Compound • Unknown compound with formula: C8H9O2N • Compound is para substituted Test/Reagent
Observation
Interference
5% HCl
NVR
Not basic
2,4-DNPH test
Yellow soln
Not an aldehyde or ketone
5% NaHCO3
NVR
Not strong acid no RCOOH
Benzenesulfonyl chloride, NaOH
Insoluble
secondary amine
FeCl3
Colored complex
Phenol group present
Hydroxamic acid test
Clear solution
No ester group present
• Unknown compound with formula: C8H9O2N • Compound is para substituted
Reminder for Final Exam: • • • •
Date: October 6, 2012 Saturday Time: 4-6 pm Coverage: expt 10 – 16 Review on different qualitative test (know reagents and result)
