Question 1

Predict the major organic product of the reaction sequence below:

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 2

Reasoning by analogy,one would predict that the reaction of carbon disulfide with sec-butylmagnesium bromide should yield which of the following (after acidification)?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 3

Choose the reagent(s)that would bring about the following reaction: CH3CH2CH2COOH --$\rightarrow$CH3CH2CH2CH2OH

Accepted Answer

A)  H2/Ni 
B)  Li/liq NH3 
C)  LiAlH[OC(CH3)3]3 
D)  NaBH4,CH3OH 
E)  LiAlH4,ether 
A)  H2/Ni 
B)  Li/liq NH3 
C)  LiAlH[OC(CH3)3]3 
D)  NaBH4,CH3OH 
E)  LiAlH4,ether

Question 4

Intramolecular dehydration to form a cyclic monoester is most likely to occur when which of the following is heated with acid?

Accepted Answer

A)  CH3CH2CH2CHOHCO2H 
B)  CH3CH2CHOHCH2CO2H 
C)  CH3CH2CH2CH2CO2H 
D)  CH3CHOHCH2CH2CO2H 
E)  HO2CCH2CH2CO2H 
A)  CH3CH2CH2CHOHCO2H 
B)  CH3CH2CHOHCH2CO2H 
C)  CH3CH2CH2CH2CO2H 
D)  CH3CHOHCH2CH2CO2H 
E)  HO2CCH2CH2CO2H

Question 5

What would be the final organic product of the following reaction?

Accepted Answer

A)  2,2-Dimethylpropanoic acid 
B)  Methyl 2,2-dimethylpropanoate 
C)  2,2-Dimethyl-1-propanol 
D)  t-Butyl methyl ether 
E)  3,3-Dimethyl-2-butanone 
A)  2,2-Dimethylpropanoic acid 
B)  Methyl 2,2-dimethylpropanoate 
C)  2,2-Dimethyl-1-propanol 
D)  t-Butyl methyl ether 
E)  3,3-Dimethyl-2-butanone

Question 6

Predict the major organic product of the reaction sequence,

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 7

An acid-catalyzed esterification (a reaction between a carboxylic acid and an alcohol)is called a ________________.

Accepted Answer

Fischer es

Question 8

A compound with the molecular formula C18H18O4 has a 1H NMR spectrum that consists of: singlet,
 $\delta$ 2.7
Singlet,
 $\delta$  3.1
Multiplet,
 $\delta$  7.3
The IR spectrum shows a strong absorption band near 1750 cm-1.The most likely structure for the compound is:

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 9

The product,Z,of the following sequence of reactions is which compound?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 10

What is the reactant of the following reaction sequence?

Accepted Answer

A)  HCO2CH2C6H5 
B)  C6H5CH2COOH 
C)  C6H5CH2Cl 
D)  C6H5CHClCOOH 
E)  O=C(CH2C6H5)2 
A)  HCO2CH2C6H5 
B)  C6H5CH2COOH 
C)  C6H5CH2Cl 
D)  C6H5CHClCOOH 
E)  O=C(CH2C6H5)2

Question 11

Which carboxylic acid would decarboxylate when heated to 100-150$\degree$C?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  More than one of these 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  More than one of these 
E)  None of these

Question 12

Which of these combinations will not produce benzoic acid?

Accepted Answer

A)  C6H5CH2OH + KMnO4/OH - /H2O,heat;then H3O+ 
B)  C6H5CH3 + KMnO4/OH - /H2O,heat;then H3O+ 
C)  C6H6 + CO2,high pressure 
D)  C6H5COCH3 + I2/OH - /H2O;then H3O+ 
E)  C6H5COCl + OH - /H2O;then H3O+ 
A)  C6H5CH2OH + KMnO4/OH - /H2O,heat;then H3O+ 
B)  C6H5CH3 + KMnO4/OH - /H2O,heat;then H3O+ 
C)  C6H6 + CO2,high pressure 
D)  C6H5COCH3 + I2/OH - /H2O;then H3O+ 
E)  C6H5COCl + OH - /H2O;then H3O+

Question 13

What would be the final product?

Accepted Answer

A)  C6H5CH2CO2CH3 
B)  C6H5CH2CH2NHCH3 
C)  C6H5CH2COCH3 
D)  C6H5CH2CH(CH3)CN 
E)  C6H5CH2CHO 
A)  C6H5CH2CO2CH3 
B)  C6H5CH2CH2NHCH3 
C)  C6H5CH2COCH3 
D)  C6H5CH2CH(CH3)CN 
E)  C6H5CH2CHO

Question 14

Which reagent would best serve as the basis for a simple chemical test to distinguish between C6H5CH=CHCOOH and C6H5CH=CHCH3?

Accepted Answer

A)  Concd.H2SO4 
B)  Br2/CCl4 
C)  CrO3/H2SO4 
D)  NaHCO3/H2O 
E)  KMnO4/H2O 
A)  Concd.H2SO4 
B)  Br2/CCl4 
C)  CrO3/H2SO4 
D)  NaHCO3/H2O 
E)  KMnO4/H2O

Question 15

Which compound would be most reactive toward nucleophilic acyl addition-elimination?

Accepted Answer

A)  CH3CO2Na 
B)  CH3COCl 
C)  (CH3CO)2O 
D)  CH3CONH2 
E)  CH3CO2CH3 
A)  CH3CO2Na 
B)  CH3COCl 
C)  (CH3CO)2O 
D)  CH3CONH2 
E)  CH3CO2CH3

Question 16

Draw the structure for 4-methylpentyl 3-ethylpentanoate.

Accepted Answer

The answer of Draw the structure for 4-methylpentyl 3-ethylpentanoate....

Question 17

Cyclic esters are called _____________,while cyclic amides are called _________.

Accepted Answer

The answer of Cyclic esters are called _____________,while cyclic amides...

Question 18

Which of the following would be the weakest acid?

Accepted Answer

A)  Benzoic acid 
B)  4-Nitrobenzoic acid 
C)  4-Methylbenzoic acid 
D)  4-Methoxybenzoic acid 
E)  4-Iodobenzoic acid 
A)  Benzoic acid 
B)  4-Nitrobenzoic acid 
C)  4-Methylbenzoic acid 
D)  4-Methoxybenzoic acid 
E)  4-Iodobenzoic acid

Question 19

What would be the final product,F,of the following sequence of reactions?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 20

Suggest a structure consistent with the following spectroscopic data:
C5H10O2
IR: 1745cm−1
1H NMR: 
triplet 3H,
 $\delta$ 0.90
multiplet 2H,
 $\delta$1.60
singlet 3H,
 $\delta$ 1.95
triplet 2H,
 $\delta$ 3.95
13C NMR
Broadband decoupled: 10.41,20.91,22.14,66.10,171.09  $\delta$
DEPT 90: no peaks
DEPT 135: 10.41,20.91 $\delta$ (positive);22.14,66.10  $\delta$(negative)

Accepted Answer

The answer of Suggest a structure consistent with the following...

Exam 17: Aldehydes and Ketones Ii Aldol Reactions

Predict the major organic product of the reaction sequence below:

Reasoning by analogy,one would predict that the reaction of carbon disulfide with sec-butylmagnesium bromide should yield which of the following (after acidification)?

Choose the reagent(s)that would bring about the following reaction: CH3CH2CH2COOH -- →\rightarrow→ CH3CH2CH2CH2OH

Intramolecular dehydration to form a cyclic monoester is most likely to occur when which of the following is heated with acid?

What would be the final organic product of the following reaction?

Predict the major organic product of the reaction sequence,

An acid-catalyzed esterification (a reaction between a carboxylic acid and an alcohol)is called a ________________.

A compound with the molecular formula C18H18O4 has a 1H NMR spectrum that consists of: singlet, δ\deltaδ 2.7 Singlet, δ\deltaδ 3.1 Multiplet, δ\deltaδ 7.3 The IR spectrum shows a strong absorption band near 1750 cm-1.The most likely structure for the compound is:

The product,Z,of the following sequence of reactions is which compound?

What is the reactant of the following reaction sequence?

Which carboxylic acid would decarboxylate when heated to 100-150 °\degree° C?

Which of these combinations will not produce benzoic acid?

What would be the final product?

Which reagent would best serve as the basis for a simple chemical test to distinguish between C6H5CH=CHCOOH and C6H5CH=CHCH3?

Which compound would be most reactive toward nucleophilic acyl addition-elimination?

Draw the structure for 4-methylpentyl 3-ethylpentanoate.

Cyclic esters are called _____________,while cyclic amides are called _________.

Which of the following would be the weakest acid?

What would be the final product,F,of the following sequence of reactions?

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Choose the reagent(s)that would bring about the following reaction: CH₃CH₂CH₂COOH -- $\rightarrow$ CH₃CH₂CH₂CH₂OH

A compound with the molecular formula C₁₈H₁₈O₄ has a ¹H NMR spectrum that consists of: singlet, $\delta$ 2.7 Singlet, $\delta$ 3.1 Multiplet, $\delta$ 7.3 The IR spectrum shows a strong absorption band near 1750 cm^-1.The most likely structure for the compound is:

Which carboxylic acid would decarboxylate when heated to 100-150 $\degree$ C? $Which carboxylic acid would decarboxylate when heated to 100-150 \degree C?$

Which reagent would best serve as the basis for a simple chemical test to distinguish between C₆H₅CH=CHCOOH and C₆H₅CH=CHCH₃?

Cyclic esters are called _____,while cyclic amides are called _.