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Questions to review for my Organic Chemistry Midterm, please provide answers

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Test 2 review
Multiple questions
Note: nomenclature questions can include R/S stereogenic centers, E or Z
alkenes.
Nomenclature
1) Aldehydes
2) Ketones
3) Carboxylic acid
4) Ester
5) Amide
6) Anhydride
7) Nitrile
Examples:
Que. 1) What is the IUPAC name of the following compound?
a. 4-phenyl-3-hexanone
b. 3-phenyl-4-hexanone
c. 1,2-diethyl-2-phenylethanal
d. 1-methyl-1-phenyl-2-butanone
Que. 2) What is the IUPAC name of the following compound?
a. (2S,4R)-dimethylpentanal
b. (2S,4S)-dimethylpentanal
c. (R)-2,4-dimethylpentanal
d. (S)-2,4-dimethylpentanal
Que. 3 ) What is the IUPAC name of the following compound
OH
a. 3,3-dimethylhexanoic acid
Screen Shot 2020-03-22 at 6.25.45 PM.png
b. 2,2-dimethylpentanoic acid
Que. 7) Which combination(s) of alkyl bromide and carbonyl compound can be
c. 2,2-dimethylpentana
used to prepare the following product by addition of the Grignard reagent derived
d. 4,4-dimethyl-6-hexanoyl acid
from the alkyl bromide to the carbonyl compound?
Que. 4) What is the IUPAC name of the following compound?
OH
a. butyl isopropanoate
b. isopropyl pentanoate
c. pentanoyl isopropane
CH& Br
CH3CH2 CH2Br
CH3CH2Br
(CH3)2CHBr
d. Isopropyloxybutanal
Que. 5) What is the IUPAC name of the following compound?
Ph
N ( CH 3 ) 2
a. only 1 and 2
a. dimethylamino-3-phenylpropanoic acid
b. only 3 and 4
b. N,N-dimethyl 2-phenylethyl amide
c. only 2 and 3
c. N,N-dimethyl 3-phenylpropanamide
d. only 1, 2 and 3
d. dimethyl 2-phenylpropanolamine
Que. 8) What is the major organic product obtained from the following reaction?
Nucleophilic addition to aldehydes and ketones
Examples:
1. LiAIHA
Que. 6) What is the major organic product obtained from the following reaction?
2. HaO
Note that Et20 is acting as solvent,
a. 2-pentanol
1. (CH3)2CHCH2MgBr
b. pentane
Et20
c. 1-pentene
2. H30*
d. (E) 2-pentene
a. 2,3-dimethyl-3-heptanol
Carbohydrates (Ch 25)
b. 2,4-dimethyl-4-heptanol
Intramolecular cyclization (hemiacetal formation)
c. 3,5-dimethyl-4-heptanol
Define relationship between different monomers as constitutional isomers,
d. 3,5-dimethyl-3-heptanol
enantiomers, diastereomers or tautomers.
Anomeric Carbon
D and L configuration
Aldose versus ketose
Furanose versus pyranose
Glycosidic linkage/name
Page 2 of 12
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Que. 9) What is the major organic product obtained from the following reaction?
Que. 11) What is the relationship between D-ribose and D-xylose?
CHO
CHO
H-SO4
OH
OH
a. 1
b. 2
CH2OH
CH2OH
C. 3
D-Ribose
D-Xylose
d. 4
a. constitutional isomers
b. enantiomers
c. diastereomers
Que. 10) What is the relationship between D-erythrose and D-threose?
d. tautomers
CHO
Que. 12) Which carbon in the following carbohydrate is th e anomeric carbon?
OH
HO
iv
H
CH2OH
CH2OH
CH2OH
.OH
D-Erythrose
D-Threose
OH
OH
a. constitutional isomers
a. i
b. enantiomers
b. ii
c. diastereomers
c. ili
d. tautomers
d. i
Que. 13) Which of the following has a D-configuration?
CHO
CHO
CHO
a. only 1 and 2
b. only 1 and 3
c. only 2 and 3
d. only 1, 2 and 3
Page 4 of 12
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Que. 14) What is (are) the major organic product(s) obtained from the following
reaction?
Que. 17) Which of the following represent a ketose?
HO
CH2 OH
HO
HO
HO
CH.OH
CH3OH
CH2OCH
CHOH
CH,OH
HOCH2
OH
-OCH3
HO
HO-
CH2OH
-OH
OH
CH2OH
HO-
- H
OH
OH
OH
OH
OCH
OH
OH
OH
OH
- OH
CH2OH
a. only 1
a. only 1 and 2
b. only 2
b. only 1 and 3
c. only 2 and 3
c. only 2 and 3
d. 1, 2 and 3
d. 1, 2 and 3
Que. 15) Which of the following represents a furanose?
Que. 18) Which of the following represent an aldose?
CHO
CH2OH HOCH ,
H-
OH
CHOH
HO
H-
-OH HO
CH2OH
OH HO
OH
a. only 1
b. only 2
a. only 1 and 2
b. only 1 and 3
c. only 3
d. only 2 and 3
c. only 2 and 3
Que. 16) Which of the following represents a pyranose?
d. 1, 2 and 3
HC
Carboxylic acids (Ch 17) and derivatives (Ch 18)
CH2OH
CHO
Aqueous solubility
HO
-OH
Boiling point
Separation of acids from carboxylates
-OH
Spectroscopy
OH
CH2OH
Rankings of acid strengths
Reactions of acids (for example with thionyl chloride)
a. only 1
Decarboxylation
b. only 2
Ester formation
Reduction
c. only 3
d. only 1 and 2
Examples:
Que. 19) Which of the following is the most soluble in water?
a. hexane
b. 1-pentanol
c. pentana
Page 6 of 12
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d. butanoic acid
Que. 24) What is the major organic product obtained from the following reaction?
Que. 20) Which of the following has the highest boiling point?
a. hexane
b. 1-pentanol
Ph
c. pentanal
d. butanoic acid
Ph
OH
acids?
Que. 21) Which of the following statements is not true regarding benzoic acid
Ph
a. The neutral acid is the predominant species in aqueous solution at pH <2.
b. The anionic carboxylate is the predominant species in aqueous solution at
a. 1
PH >7.
b. 2
c. Sodium benzoate is less soluble in water than benzoic acid.
c. 3
d. Benzoic acid is extracted out of diethyl ether by treatment with aqueous
d. 4
sodium bicarbonate
Que. 25) What is the best choice of reagent(s) to perform the following
Que. 22) Which of the following is the correct order of decreasing acid strength
transformation
(more acidic > less acidic)?
a. ICH2COOH > CICH2COOH > FCH2COOH
b. Cl2CHCOOH > CICH2COOH > CH3COOH
C. CH3CH2OH > FCH2COOH > CICH2COOH
OCH3
d. CH3COOH > FCH2COOH > CH3CH2OH
a. CH3OH, H2SO4
b. CH31, H2SO4
Que. 23) What is the major organic product obtained from the following reaction?
c. NaOCH3
d. CH3L
Que. 26) What is the best choice of reagent(s) to perform the following
transformation?
"OH
SOCK2
OH
Ph
OH
a. 1. LiAlH4; 2. H30+
Ph
b. H2, Pt
c. 1. NaBH4; 2. H20
d. Nah
a. T
. 2
Que. 27) Consider the following 'H NMR to answer the following question.
C. 3
d 4
Page 8 of 12
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a. 1 = lactone; 2 = ester; 3 = amide
b. 1 = ester; 2 = ester; 3 = imide
c. 1 = ester; 2 = imide; 3 = amide
d. 1 = lactone; 2 = anhydride; 3 = imide
Que. 30) What is the correct assignment of the functional groups in the following
10
compounds?
P-44-081
Chemical shift (8)
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/
(National Institute of Advanced Industrial Science and Technology, 11-07-08)
This compound is known to contain both a -C=O group and an -OH group.
Based on this spectrum, this compound would be classified as aliphatic
NHCH ,
carboxylic acid
a. True
a. 1 = amide; 2 = imide; 3 = nitrile
b. False
b. 1 = lactam; 2 = amide; 3 = imide
c. 1 = lactam; 2 = imide; 3 = amide
Que. 28) What is the correct assignment of the names of the following
d. 1 = imide; 2 = amide; 3 = lactam
substituted benzenes?
Que. 31) Which of the following is the correct order of decreasing reactivity in
hydrolysis reactions (more reactive > less reactive)?
Ph-C=N
Ph-
ph -
a. esters > amides > acid chlorides
b. amides > acid chlorides > esters
1
2 NH 2
3 OH
c. acid chlorides > esters > amides
a. 1 = benzonitrile; 2 = benzyl amine; 3 = benzyl alcohol
d. esters > acid chlorides > amides
b. 1 = benzyl amine; 2 = benzonitrile; 3 = benzamide
c. 1 = benzamide; 2 = benzonitrile; 3 = benzoic acid
Que. 32) Which of the following can be made by acid-promoted hydrolysis of a
d. 1 = benzonitrile; 2 = benzamide; 3 = benzoic acid
nitrile?
an acid
Que. 29) What of the following is the correct assignment of the classes of the
an alcohol
following compounds?
an imine
an imide
Page 10 of 12
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Que. 33) What is the major organic product obtained from the following reaction?
HO
HO
a. 1
b. 2
c. 3
d. 4
Que. 34) What is the major organic product obtained from the following reaction?
OH
OH
OH
2
a. 1
b. 2
C. 3
d. 4
Page 12 of 12

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