Question 1

The product of the following reaction sequence is nervonic acid.What is the structure of nervonic acid?

Accepted Answer

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

Question 2

Draw the most stable chair conformation of menthol and label each substituent as axial or equatorial.

Accepted Answer

All substituents are equatorial.

Question 3

Which of these lipids yields choline upon hydrolysis?

Accepted Answer

A) A lecithin only 
B) A sphingomyelin and a cerebroside 
C) A cephalin and a lecithin 
D) A cerebroside and a cephalin 
E) A lecithin and a sphingomyelin 
A) A lecithin only 
B) A sphingomyelin and a cerebroside 
C) A cephalin and a lecithin 
D) A cerebroside and a cephalin 
E) A lecithin and a sphingomyelin E

Question 4

Terpenes are built up from two or more five-carbon units known as ___.

Accepted Answer

The answer of Terpenes are built up from two or...

Question 5

Which fatty acid is likely to occur commonly in natural sources?

Accepted Answer

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

Question 6

Choline cannot be found as a product of hydrolysis of any representative of this class of lipids.

Accepted Answer

A) Cerebrosides 
B) Phosphatidylserine 
C) Plasmalogens 
D) Waxes 
E) None of these choices yield choline upon hydrolysis 
A) Cerebrosides 
B) Phosphatidylserine 
C) Plasmalogens 
D) Waxes 
E) None of these choices yield choline upon hydrolysis

Question 7

The synthesis of cortisone required placing a ketone function at the 11-position of a steroid.Where is position 11?

Accepted Answer

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

Question 8

What is a mixed triacylglycerol?

Accepted Answer

A) It is a lipid where a terpene is esterifying glycerol 
B) It is a triester of glycerol where the acyl groups are identical 
C) It is a triester formed by glycerol and acetic acid 
D) It is a triester of glycerol where the fatty acids are not all identical 
E) It is an ester between glycerol and cholesterol 
A) It is a lipid where a terpene is esterifying glycerol 
B) It is a triester of glycerol where the acyl groups are identical 
C) It is a triester formed by glycerol and acetic acid 
D) It is a triester of glycerol where the fatty acids are not all identical 
E) It is an ester between glycerol and cholesterol

Question 9

Which of the following statements regarding triacylglycerols is not true?

Accepted Answer

A) Some undergo autoxidation with oxygen from air. 
B) They are solid if they do not have alkene groups. 
C) They form lipid bilayers. 
D) They form micelles in water. 
E) Two of these choices are false statements. 
A) Some undergo autoxidation with oxygen from air. 
B) They are solid if they do not have alkene groups. 
C) They form lipid bilayers. 
D) They form micelles in water. 
E) Two of these choices are false statements.

Question 10

Salts of long-chain fatty acids are known as ___.

Accepted Answer

The answer of Salts of long-chain fatty acids are known...

Question 11

Which of the following could be used to prepare myristic acid,CH3(CH2)12COOH?

Accepted Answer

A) CH3(CH2)11CH2Br,CN-,heat; then H3O+,heat 
B) CH3(CH2)11CH2Br,Mg,(C2H5)2O; then CO2; then H3O+ 
C) CH3(CH2)12CHO,Ag2O,OH-; then H3O+ 
D) Two of these choices. 
E) All of these choices. 
A) CH3(CH2)11CH2Br,CN-,heat; then H3O+,heat 
B) CH3(CH2)11CH2Br,Mg,(C2H5)2O; then CO2; then H3O+ 
C) CH3(CH2)12CHO,Ag2O,OH-; then H3O+ 
D) Two of these choices. 
E) All of these choices.

Question 12

Myelin,the protective coating around nerve fibers,is made up of ___.

Accepted Answer

sphingolip

Question 13

How many stereogenic centers are there in cholesterol?

Accepted Answer

A) 2 
B) 4 
C) 6 
D) 8 
E) 16 
A) 2 
B) 4 
C) 6 
D) 8 
E) 16

Question 14

Rank the following fatty acids according to increasing melting point. I: CH3(CH2)16CO2H
II: CH3(CH2)7CH=CH(CH2)7CO2H (cis)
III: CH3(CH2)7CH=CH(CH2)7CO2H (trans)
IV: HO2C(CH2)7CH=CHCH2CH=CH(CH2)7CH3 (cis,cis)

Accepted Answer

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

Question 15

How many chiral centers does prostaglandin E2 have? Assign R,S configurations to these centers.

Accepted Answer

The answer of How many chiral centers does prostaglandin E2...

Question 16

How could you synthesize stearolic acid,CH3(CH2)7C=C(CH2)7COOH from oleic acid,CH3(CH2)7CH=CH(CH2)7COOH?

Accepted Answer

A) Br2,CCl4; then 3 NaNH2,heat; then H3O+ 
B) Li,liq.NH3; then H3O+ 
C) H2,Pd 
D) Peracid; then H3O+; then HA,H2O,heat 
E) Excess HCl; then KOH,C2H5OH,heat 
A) Br2,CCl4; then 3 NaNH2,heat; then H3O+ 
B) Li,liq.NH3; then H3O+ 
C) H2,Pd 
D) Peracid; then H3O+; then HA,H2O,heat 
E) Excess HCl; then KOH,C2H5OH,heat

Question 17

Which of these is a detergent?

Accepted Answer

A) CH3(CH2)16COO-Na+ 
B) [CH3(CH2)14COO-]2Ca2+ 
C) CH3(CH2)10CH2SO3-Na+ 
D) HOCH2CHOHCH2OH 
E) CH3(CH2)14CH2SH 
A) CH3(CH2)16COO-Na+ 
B) [CH3(CH2)14COO-]2Ca2+ 
C) CH3(CH2)10CH2SO3-Na+ 
D) HOCH2CHOHCH2OH 
E) CH3(CH2)14CH2SH

Question 18

Which is not a correct statement concerning naturally occurring triacylglycerols?

Accepted Answer

A) The greater the degree of unsaturation,the higher the melting point. 
B) Saponification yields glycerol and a mixture of carboxylic acid salts. 
C) Solid triacylglycerols are termed "fats." 
D) Regardless of the exact nature of the R groups,such compounds are water-insoluble. 
E) Such compounds frequently are called "triglycerides." 
A) The greater the degree of unsaturation,the higher the melting point. 
B) Saponification yields glycerol and a mixture of carboxylic acid salts. 
C) Solid triacylglycerols are termed "fats." 
D) Regardless of the exact nature of the R groups,such compounds are water-insoluble. 
E) Such compounds frequently are called "triglycerides."

Question 19

Identify the bonds that link the isoprene units in $\alpha$ -farnesene,shown below.How are these units linked: head to head,tail to head or tail to tail?   $\alpha$-farnesene

Accepted Answer

The answer of Identify the bonds that link the isoprene...

Question 20

The compounds I and II are:

Accepted Answer

A) Prostaglandins. 
B) Terpenoids. 
C) I is a prostaglandin; II is not a prostaglandin. 
D) I is an E type prostaglandin; II is an F type prostaglandin. 
E) Both are fatty acids. 
A) Prostaglandins. 
B) Terpenoids. 
C) I is a prostaglandin; II is not a prostaglandin. 
D) I is an E type prostaglandin; II is an F type prostaglandin. 
E) Both are fatty acids.

Exam 23: Lipids

The product of the following reaction sequence is nervonic acid.What is the structure of nervonic acid?

Draw the most stable chair conformation of menthol and label each substituent as axial or equatorial.

Which of these lipids yields choline upon hydrolysis?

Terpenes are built up from two or more five-carbon units known as ___.

Which fatty acid is likely to occur commonly in natural sources?

Choline cannot be found as a product of hydrolysis of any representative of this class of lipids.

The synthesis of cortisone required placing a ketone function at the 11-position of a steroid.Where is position 11?

What is a mixed triacylglycerol?

Which of the following statements regarding triacylglycerols is not true?

Salts of long-chain fatty acids are known as ___.

Which of the following could be used to prepare myristic acid,CH3(CH2)12COOH?

Myelin,the protective coating around nerve fibers,is made up of ___.

How many stereogenic centers are there in cholesterol?

Rank the following fatty acids according to increasing melting point. I: CH3(CH2)16CO2H II: CH3(CH2)7CH=CH(CH2)7CO2H (cis) III: CH3(CH2)7CH=CH(CH2)7CO2H (trans) IV: HO2C(CH2)7CH=CHCH2CH=CH(CH2)7CH3 (cis,cis)

How many chiral centers does prostaglandin E2 have? Assign R,S configurations to these centers.

How could you synthesize stearolic acid,CH3(CH2)7C=C(CH2)7COOH from oleic acid,CH3(CH2)7CH=CH(CH2)7COOH?

Which of these is a detergent?

Which is not a correct statement concerning naturally occurring triacylglycerols?

Identify the bonds that link the isoprene units in α\alphaα -farnesene,shown below.How are these units linked: head to head,tail to head or tail to tail? α\alphaα -farnesene

The compounds I and II are:

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which of the following could be used to prepare myristic acid,CH₃(CH₂)₁₂COOH?

Rank the following fatty acids according to increasing melting point. I: CH₃(CH₂)₁₆CO₂H II: CH₃(CH₂)₇CH=CH(CH₂)₇CO₂H (cis) III: CH₃(CH₂)₇CH=CH(CH₂)₇CO₂H (trans) IV: HO₂C(CH₂)₇CH=CHCH₂CH=CH(CH₂)₇CH₃(cis,cis)

How could you synthesize stearolic acid,CH₃(CH₂)₇C=C(CH₂)₇COOH from oleic acid,CH₃(CH₂)₇CH=CH(CH₂)₇COOH?