CHEM 222 Lecture Notes - Lecture 17: Aminolysis, Ethyl Group, Penicillin

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17 Mar 2017

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Trends in acidity: electronegative element makes h more acidic since stabilizing the anion (weaker conjugate base, carboxylic acids are better acids than alcohols, second oxygen, so when remove the h get resonance stabilized anion. In the first one, the electron withdrawing group is closer and so has stronger effect: benzene has resonance, and acts as ewg, more alkyl groups are more electron donating so slight decrease in acidity. Key features of strong nucleophilic addition: tetrahedral intermediate ==> nu adds to the c=o, elimination --labile c-z leads to re-forming of c=o, irreversible addition --barrier for reverse reaction is too large. Weak nucleophilic addition-elimination: used to make esters from carboxylic acids, under acidic conditions, generally reversible, protonate before adding the nucleophile, to make carbonyl more electrophilic. Practice acidic hydrolysis: need acidic conditions for an ester --protonate first before adding in water, no net gain, acting as catalyst.

Related Questions

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graylouse963

Why do ionic compounds dissolve well in water? Select all that are true.

Question 5 options:

Because water and ionic compounds are both polar

Water molecules have partial charges that attract the ions in the solid compound, causing it to dissociate into separated ions

Because organic compounds are nonpolar

Water molecules can surround an ion, and neutralize the ion's charge using either it's partial positive or negative side.

The individual ions are solvated by water molecules which stabilizes the ions

2. Which compound is soluble in ether but not soluble in aqueous sodium hydroxide?

Question 2 options:

	ArOH
	Ar
	ArCOOH

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When you have a two-layer mixture of water and tert-butyl methyl ether, what physical property of these liquids assures you that the ether is the top layer?

Question 4 options:

low density was my answer was

You perform each extraction twice, first with 1 mL and second with 0.15 mL. Why is the second extraction necessary?

Question 8 options:

	several small extractions is better than one large one
	to remove any orgnaic material contaninating tube 2
	to remove any remaining neutral compound

7. Which of the following reactions is not favorable?

Question 7 options:

	ArCOOH + NaOH â ArCOO^-Na⁺ + H₂O
	ArOH + NaHCO₃ â ArO^-Na⁺ + CO₂ + H₂O
	ArCOOH + NaHCO₃ â ArCOO^-Na⁺ + CO₂ + H₂O

9.Why is phenol more acidic than an aliphatic alcohol?

Question 9 options:

	Its conjugates baseâs negative charge is localized on the oxygen
	Phenols have a stronger O-H bond
	Only the phenol can form hydrogen bonds
	Its conjugated base is stabilized by resonance

Which aqueous base reacts with a carboxylic acid but not with phenol? Why?

Question 10 options:

	Sodium bicarbonate, it is a weaker base and will only react with strong acids
	Sodium hydroxide, it is a strong base and will only react with strong acids
	Sodium bicarbonate, it is a weak base and will only react with weak acids
	Sodium hydroxide, it is a strong base and will only react with weak acids

1)The reaction of benzamide, C6H5CONH2, with LiAlH4 yields which of the following compounds?
A.benzoic acid
B.benzonitrile
C.benzylamine
D.ammonium benzoate
E. none of the above

2) Electron-releasing groups bonded to an amine nitrogen increases it basicity. T or F?

3) Ammonium salts are water soluble. T or F?

4)A compound which is insoluble in water but which dissolves in dilute hydrochloric acid is

A. probably an amide
B.possibly a carboxylic acid
C.almost certainly an amine
D.probably neither acidic nor basic
E.probably an ester

5)Primary and secondary amines react with nitrous acids to form stable diazonium salts. T or F?

6). Dimethylethylamine is classified as a

A.primary amine
B.secondary amine
C.tertiary amine
D.quaternary amine

7)Heating a(n) _______ results in a Cope elimination.

A.amine oxide
B.imine
C.enamine
D.oxime
E.quaternary ammonium salt

8) Aniline is less basic than methylamine because:

A. resonance in aniline increases the electron density on nitrogen: this effect is not possible for methylamine.

B.resonance in aniline stabilizes the nonprotonated base but does not stabilize the protonated base: in methylamine resonance is of no importance for the protonated or unprotonated forms.

C.the acid-base reaction of aniline with a proton is kinetically rather than thermodynamically controlled.

D.the ortho hydrogens of aniline interfere with protonation of its amino group.

E.The question is incorrect, aniline is actually more basic than methlamine.

9) Amines can best be separated from nitro compounds by an extraction procedure employing diethyl ether and:

A.water
B.aqueous HCl
C.aqueous NaOH
D.concentrated H2SO4

10) An amino group is a powerful ortho-para director. T or F?

11) What is the hybridization of the nitrogen atom in CH3NH2?

A. sp
B.sp2
C.sp3
D.s-sp3
E.a primary amine

12) Diazonium salts readily couple with phenols and aromatic amines to form azo compounds. T or F?

13) Aniline is a stronger base than ammonia. T or F?

14) What type of amine is tert-butyl amine?

A.primary
B.secondary
C.tertiary
D.quaternary
E.none of these

CHEM 222 Lecture Notes - Lecture 17: Aminolysis, Ethyl Group, Penicillin

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