Exam 3
Provide the IUPAC name for the following compound, including stereochemical designators as appropriate.
(S,Z)-2-bromohex-3-enal
Provide the proper IUPAC name for CH3CHOHCH2COCH2C(CH3)2CH2CH3.
2-hydroxy-6,6-dimethyl-4-octanone
Provide the IUPAC name for (CH3)3CCH2CHClCH2CHO.
3-chloro-5,5-dimethylhexanal
Name the following compound.
4,7,7-trimethyl2-octanone or 4,7,7,-trimethyloctan-2-one
Provide the proper IUPAC name for (CH3)2CHCH2CH2COCH=CH2
6-methylhept-1-en-3-one
Which of the following reactions is favorable, in the direction indicated, under fairly "normal" laboratory conditions?
A)
Show how you would perform the following synthesis.
A) 1. O3 2. (CH3)2S
Which sequence ranks the following carbonyl compounds in order of increasing rate of nucleophilic addition?
A) 2<3<1
Which sequence ranks the following carboxylic acid derivatives in order of increasing rate of hydrolysis?
A) 2<3<1
Which compound will show an intense peak in the mass spectrum at m/z 58?
A) CH3COCH2CH2CH3
Shown below is the structure of Lactimidomycin, a potent inhibitor of cell migration, proliferation and protein synthesis. Identify the carboxylic acid derivative/s in the structure of Lactimidomycin.
A) Ester
Acetals will react with ________.
A) H3O+
What is the correct IUPAC name for the following compound?
A) N-ethyl-2,N-dimethylbutanamide
What product will result from the reaction shown?
A) acetal
Which of the following compounds is most soluble in water?
A) acetone
What type of compound results from the reaction of ethyl formate with cyclohexylamine?
A) amide
The first mechanistic step in the direct reaction of an amine with a carboxylic acid to produce an amide is ________.
A) an acid-base reaction
106) Mark all the sequences of reactions that convert a carboxylic acid to an aldehyde. (More than one answer is possible.) A) 1) CH2N2 2) DIBAL 3) H3O+ B) 1) NaBH4 2) H3O+ 3) PCC C) 1) SOCl2 2) LiAl(Ot-Bu)3H D) 1) LiAlH4 2) Ag(NH3)2OH
A) and C
In 1H NMR, the chemical shifts for protons α to a carbonyl group ________.
A) are similar for all acid derivatives
The hydrolysis of esters, amides, and nitriles ________.
A) can be carried out under acidic or basic conditions
When an aldehyde is reacted with HCN in the presence of KCN, what product is formed?
A) cyanohydrin
Which of the following describes a synthesis of an aldehyde?
A) hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst
Two equivalents of methyl magnesium bromide will add to ________.
A) lactones
Why are the OH groups of carboxylic acids more acidic than alcohols?
A) resonance stabilization of the carboxylate ion
What is the common name for the following compound?
A) γ-hydroxyvaleric acid
In the proton NMR spectra of aldehydes and ketones, the protons bonded to carbons adjacent to the carbonyl group typically fall into which of the chemical shift ranges below?
B) 2.0-3.0 ppm
Which of the following correctly describes the bond angle and hybridizations present in formaldehyde?
B) C, sp2; O, sp2; HCO, ~120°
What compound is produced when cyclohexene is treated with concentrated KMnO4?
B) adipic acid
The cyclic structure of glucose is shown below. What functional groups are present in this molecule?
B) hemiacetal
Cyclic amides are called ________.
B) lactams
In a carboxylic acid, the hybridization of the C is ________ and the OCO bond angle is ________.
B) sp2; greater than 120°
Amides are less basic than amines because ________.
B) the carbonyl group withdraws electrons by resonance
What is the product of the following reaction?
C) (CH3)3CCH2CH2CH2CH2NH2
Which of the following reagents convert(s) benzoyl chloride to phenyl propyl ketone?
C) (CH3CH2CH2)2CuLi
How would you perform the following transformation?
C) 1. DIBAL-H 2. H2O
Which of the following would be the preferred reagents used in the following synthesis?
C) 1. LiAlH4-THF 2. H3O+
While the carbonyl stretching frequency for simple aldeydes, ketones, and carboxylic acids is about 1710 cm-1, the carbonyl stretching frequency for esters is about ________.
C) 1735 cm-1
Which of the reagents listed below would work best in the following reaction?
C) BH3 -THF
In nucleophilic acyl substitution ________.
C) addition to the carbonyl by a nucleophile is followed by loss of the leaving group
Oxidation of a 1° alcohol with pyridinium chlorochromate results in the production of ________.
C) an aldehyde
After completing the synthesis of 3-methylpentanoic acid, which of the following treatments will neutralize the mineral acids and facilitate the distribution of the organic acid from the organic layer to the aqueous extraction layer?
C) extraction with aqueous NaHCO3
Which of the following is the strongest acid?
C) trichloroacetic acid
What is the common name for the following carboxylic acid derivative?
C) β-hydroxyvaleronitrile
E) 2-methylcyclohexanone < cyclohexanone < CH3CHO < H2CO
CH3COCH2CH3 < CH3CH2CHO < H2CO < Cl3CCHO
By which single reaction can benzene be readily converted into acetophenone?.
CH3COCl, AlCl3 - a Friedel-Crafts acylation reaction
The most characteristic IR stretch of butanenitrile occurs at approximately what wavenumber?
D) 2200 cm-1
Which of the following sequences ranks the structures below in order of increasing acidity?
D) 2<1<3
Predict the major organic product from the following reaction.
D) 2° amide
Another name for β-methoxybutyraldehyde is ________.
D) 3-methoxybutanal
What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence of steps?
D) 3-methylbutanoic acid
What compound is produced when N,N-dimethylpropanamide is treated with LiAlH4?
D) CH3CH2CH2N(CH3)2
Which of the following statements is true?
D) The carbonyl carbon in a carboxylic acid gives a 13C signal in the same region as a carbonyl carbon from an ester or amide in the range of 150 to 180 ppm.
Which of the following is the most reactive carboxylic acid derivative?
D) acid chloride
Phthalic acid produces what acid derivative upon heating?
D) an anhydride
Acid chlorides can be prepared from carboxylic acids by treatment with ________.
D) both A and B
Which of the following compound(s), when reacted with aniline, yield(s) acetanilide?
D) both A and B
The combination of a carbonyl group and a hydroxyl group on the same carbon atom is called a ________ group.
D) carboxyl
Which of the following is the strongest acid?
D) fluoroacetic acid
An acid which could not be prepared by the reaction of an organic halide with cyanide ion followed by acid hydrolysis of the nitrile is ________.
D)(CH3)3CCO2H
Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing Keq for this equilibrium?
E) 2-methylcyclohexanone < cyclohexanone < CH3CHO < H2CO
In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about ________.
E) 200 ppm
Which of the following compounds would show only one triplet in its off resonance decoupled spectrum?
E) 3-pentanone
In the mass spectrum of pentanoic acid, the base peak occurs at m/z ________.
E) 60
Which of the following is the strongest acid?
E) O2NCH2CO2H
What intermediate occurs when a ketone undergoes a Wolff-Kishner reduction?
E) a hydrazone
Esters and amides are most easily made by nucleophilic acyl substitution reactions on
E) acid chlorides.
hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst
E) all of the above
Which of the following compounds is(are) hydrolyzed to butanoic acid upon heating in H2O H2SO4?
E) both A and C
Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation?
E) both b and d
Carboxylic acids can be made from Grignards by treating the Grignard reagents with ________.
E) carbon dioxide
The hydrolysis of esters in base is called ________.
E) saponification
What two alkenes, which contain only one double bond, yield exclusively propanoic acid upon oxidation with hot concentrated KMnO4?.
E- and Z-hex-3-ene
Arrange the following three amides in order of increasing boiling point: propanamide, N- methylacetamide, and N,N-dimethylformamide.
N,N-dimethylformamide < N-methylacetamide < propanamide
Provide the major organic product which results when PhCHOHCH3 is treated with PCC.
PhCOCH3
Provide the structure of benzophenone.
PhCOPh
How does the O-H stretch in the IR spectrum of a carboxylic acid differ from the O-H stretch of an alcohol?
The O-H stretch of a carboxylic acid is broader and shifted to lower wavenumbers.
Acids can be reduced to aldehydes by _______
_.B) conversion to the acid chloride followed by treatment with LiAlH[OC(CH3)3]3
An unknown compound is insoluble in water but dissolves in an aqueous solution of sodium bicarbonate with a release of carbon dioxide bubbles. The compound is almost certainly
a carboxylic acid
What are the major organic products when 1 equivalent of acetic formic anhydride reacts with 1 equivalent of methanol?
acetic acid and methyl formate
Carbonated beverages typically have pHs below 7.0. What acid is present which lowers the pH? Show the reaction by which it is formed..
carbonic acid, CO2 + H2O → H2CO3
Name the compound which results when δ-valerolactone is heated in a large excess of methanol in the presence of catalytic acid.
methyl 5-hydroxypentanoate
What compound results when ethyl benzoate is stirred in methanol containing a trace of HCl and by what name is this process known?
methyl benzoate; transesterification
List the following five compounds, ethanamide, 1-propanol, methyl formate, acetic acid, and propanenitrile, in order of increasing boiling point. Start with the lowest boiling compound.
methyl formate < propanenitrile < 1-propanol < acetic acid < ethanamide
Are carboxylic acids of more than 10 carbons more soluble in polar or nonpolar solvents?
nonpolar solvents
Name the following compound.
p-chlorobenzaldehyde or 4-chlorobenzaldehyde
2-Phenylethanol yields what acid upon treatment with cold chromic acid?
phenylacetic acid
What are the products of the reaction of phenylacetic acid with oxalyl chloride?
phenylacetyl chloride, HCl (g), CO (g), and CO2 (g)
What salt results from the reaction of benzoic acid with potassium hydroxide?
potassium benzoate
What products result from the reaction of sodium propanoate with hydrobromic acid?
propanoic acid and sodium bromide
Hept-3-yne yields what acids upon treatment with concentrated permanganate of ozone followed by water?
propanoic and butanoic acids
