Deck 20: Organic Chemistry II

Question 1

Consider the reaction
CH₃(CH₂)₄CH₂CH(Br)CH₃ + NaOH $\rightarrow$ CH₃(CH₂)₄CH₂CH(OH)CH₃
(optically pure enantiomer)
The rate law for this reaction over a wide range of [OH^-] is R = k₁[RX] + k₂[RX][OH^-] where RX is 2-bromooctane and k₂/k₁ = 20.At very low hydroxide ion concentration,

A)the product of the reaction does not rotate the plane of polarized light.
B)the product formed is CH₃(CH₂)₄CH=CHCH₃ and not the alcohol.
C)the reaction proceeds by an S_N2 mechanism.
D)the hydroxide ion attacks the face of the carbocation in a concerted mechanism on the face opposite the leaving group.
E)the product is optically active and rotates the plane of polarized light in the opposite direction with respect to 2-bromooctane.

Answer 1

the product of the reaction does not rotate the plane of polarized light.

Question 2

Which of the following compounds is most likely to undergo nucleophilic substitution by an S_N2 reaction?

A)CH₃CH₂CH₂Br
B)(CH₃CH₂)₃CBr
C)CH₃CH₂CBr(CH₃)CH₃
D)(CH₃)₃CBr

Answer 2

CH₃CH₂CH₂Br

Question 3

Consider the reaction
CH₃(CH₂)₄CH₂CH(Br)CH₃ + NaOH $\rightarrow$ CH₃(CH₂)₄CH₂CH(OH)CH₃
(optically pure enantiomer)
If 2-bromooctane rotates the plane of polarized light to the right while the product rotates the plane of polarized light to the left,which of the following statements is true?

A)This is an example of an elimination reaction.
B)The reaction occurs by an S_N2 mechanism.
C)The reaction occurs by an S_N1 mechanism.
D)This is an example of an addition reaction.
E)This is an example of an electrophilic substitution.

Answer 3

The reaction occurs by an S_N2 mechanism.

Question 4

Which of the following do not function as nucleophiles in nucleophilic substitution reactions?
1.H₂O
2.SH^-
3.CN^-
4.PH₃ 5.CH₃CH₂O^-

A)1 and 4
B)2,3,and 5
C)1,2,and 4
D)5
E)4

Question 5

Ethers are less volatile than alcohols of the same molar mass.

Question 6

Which of the following is a tertiary alcohol?

A)C₆H₅CH₂OH
B)C(CH₃)₃OH
C)CH₃CH₂OH
D)CH(CH₃)₂OH
E)CH₃(CH₂)₃OH

Question 7

The -OH group occurs in

A)aldehydes and alcohols.
B)alcohols only.
C)alcohols,phenols,and carboxylic acids.
D)phenols and ketones.
E)ketones and carboxylic acids.

Question 8

If 2-bromobutane reacts with OH^- by an S_N2 mechanism,the product is optically active and has the reverse chirality compared to the reactant.

Question 9

Which of the following is the most volatile?

A)CH₃CH(OH)CH₂CH₃
B)CH₃(CH₂)₃OH
C)(CH₃)₂C(OH)CH₃
D)(CH₃)₃COH
E)CH₃CH₂OCH₂CH₃

Question 10

The compound 3-bromo-3-ethylpentane likely undergoes nucleophilic substitution by an S_N1 reaction.

Question 11

How many secondary alcohols are there with the formula C₄H₉OH?

A)4
B)2
C)3
D)1
E)5

Question 12

In the S_N1 mechanism for nucleophilic substitution,the carbocation produced is a Lewis acid and the nucleophile is a Lewis base.

Question 13

What is the product of the reaction
C₅H₉CH₂CH₂Br + NaCN $\rightarrow$

Question 14

If 2-bromobutane reacts with OH^- by an S_N1 mechanism,the product is optically active and has the reverse chirality compared to the reactant.

Question 15

The compound CH₃CH₂OCH₂CH₃ is

A)an alcohol.
B)an ester.
C)a ketone.
D)an aldehyde.
E)an ether.

Question 16

Which of the following is most volatile?

A)(CH₃)₂C(OH)CH₃
B)(CH₃)₃COH
C)CH₃CH(OH)CH₂CH₃
D)CH₃(CH₂)₃OH
E)CH₃CH₂CH₂CH₃

Question 17

How many primary alcohols are there with the formula C₄H₉OH?

A)4
B)3
C)5
D)1
E)2

Question 18

Where is the electrophilic site in the compound 2-bromo-2-methylbutane?

Question 19

The major product of the reaction of (CH₃)₂CHCH(Br)CH₃ with concentrated KOH in alcohol solvent is

A)2-methyl-2-butene.
B)3-methyl-1-butene.
C)2-hydroxy-3-methylbutane.
D)pentene.
E)3-methylbuatanol.

Question 20

Which of the following is a secondary alcohol?

A)CH₃CH₂OH
B)C₆H₅CH₂OH
C)C(CH₃)₃OH
D)CH₃(CH₂)₃OH
E)CH(CH₃)₂OH

Question 21

The formation of an amide from a primary amine and a carboxylic acid is

A)a substitution reaction.
B)an oxidation reaction.
C)an addition reaction.
D)an elimination reaction.
E)a condensation reaction.

Question 22

Which of the following compounds is the strongest acid?

A)5
B)3
C)2
D)1
E)4

Question 23

When an ester is formed via a condensation reaction with elimination of water,the oxygen atom in the water molecule comes from

A)the hydroxyl group of the acid.
B)the alcohol.
C)the aldehyde.
D)the carbonyl group of the acid.
E)the solvent.

Question 24

Oxidation of 2-propanol gives

A)acetaldehyde.
B)propanoic acid.
C)acetone.
D)dimethyl ether.
E)acetic acid.

Question 25

What is the product of the following reaction?

Question 26

All the following produce a silver mirror with Tollens reagent except

A)HCHO.
B)CH₃CH₂CH(CHO)CH₃.
C)CH₃CH₂COCH₃.
D)CH₃(CH₂)₃CHO.
E)CH₃CH₂CHO.

Question 27

The product of the reaction of CH₃CH₂CHO with excess KMnO₄(aq)in acidic solution is

A)CH₃CH₂COOH.
B)CH₃CH₂COCH₂CH₃.
C)CH₃COOH.
D)CH₃CH₂CH₃.
E)CH₃CH₂OH.

Question 28

The carbonyl group occurs in all the following except

A)amides.
B)ketones.
C)carboxylic acids.
D)aldehydes.
E)phenols.

Question 29

There are two isomeric butanals that differ in the position of the carbonyl group.

Question 30

Oxidation of secondary alcohols produces

A)acids.
B)aldehydes.
C)ketones.
D)Secondary alcohols cannot be oxidized.
E)ethers.

Question 31

When aldehydes react with Tollens reagent,

A)a red precipitate forms.
B)silver ions are produced.
C)a ketone is produced.
D)the aldehyde reduces silver ions.
E)an alcohol is produced.

Question 32

Which of the following produces a silver mirror with Tollens reagent?

A)CH₃COOH
B)CH₃C(O)OCH₃
C)CH₃COCH₃
D)CH₃OCH₃
E)CH₃CHO

Question 33

To produce butanone,which of the following should be reacted with Na₂Cr₂O₇(aq),H₂SO₄(aq)?

A)CH₃CH₂CH(OH)CH₃
B)CH₃CH₂CH(COOH)CH₃
C)CH₃CH₂CH(CH₂OH)CH₃
D)(CH₃)₂CHCHO
E)CH₃CH₂CH₂CH₂OH

Question 34

Predict the product of the reaction of acetic acid with trimethylamine.

A)CH₃CON(CH₃)₃⁺
B)CH₃CONHCH₃
C)CH₃CON(CH₃)₂
D)CH₃CONH₂
E)No reaction occurs.

Question 35

Name the compound CH₃COO(CH₂)₄CH₃.

A)Methyl pentanoate
B)Hexanoic acid
C)2-hexanone
D)Pentyl acetate
E)Butyl acetate

Question 36

Predict the product(s)of the reaction of acetic acid with methylamine at 200^oC.

A)CH₃COO^-and CH₃NH₃⁺
B)No reaction occurs.
C)CH₃C(O)OCH₃
D)CH₃CONHCH₃
E)CH₃CONH₂

Question 37

The ester CH₃COO(CH₂)₄CH₃,which is responsible for the odor of bananas,can be prepared from

A)CH₃CH₂OH and CH₃(CH₂)₃COOH.
B)CH₃CHO and CH₃(CH₂)₃CH₂OH.
C)CH₃COOH and CH₃(CH₂)₃CH₂OH.
D)CH₃CHO and CH₃(CH₂)₃COOH.
E)CH₃COOH and CH₃(CH₂)₃CHO.

Question 38

Both C₆H₅OH and C₆H₅CH₂OH are weak acids with K_a values about 10^-10

Question 39

Which of the following can produce esters?

A)A primary alcohol plus K₂Cr₂O₇(aq),H₂SO₄
B)An alcohol plus an aldehyde
C)An aldehyde plus KMnO₄(aq)in acidic solution
D)An acid plus an alcohol
E)An acid plus an aldehyde

Question 40

When aldehydes react with Tollens reagent,

A)a red precipitate forms.
B)a ketone is produced.
C)silver ions are produced.
D)an alcohol is produced.
E)a carboxylic acid is produced.

Question 41

The systematic name of CH₃CH₂CH(CHO)CH₃ is

A)2-ethylpropanal.
B)2-pentanal.
C)3-methylbutanal.
D)2-pentanone.
E)2-methylbutanal.

Question 42

Which of the following would be attacked by a nucleophilic reagent?

A)2,3,and 5
B)1 and 4
C)3 and 5
D)2 and 5
E)3 only

Question 43

Which of the following reactants can be used to produce propanamide?

A)5 and 6
B)4 and 7
C)2,4,and 11
D)4 and 5
E)2,4,and 8

Question 44

Which of the following reactants can be used to produce butanamide?

A)1 and 6
B)1 and 3
C)4 and 7
D)8 and9
E)6 and 11

Question 45

Condensation polymerization involves the use of

A)one or two monomers,each with a nitrile group.
B)one or two monomers with reactive groups at each end of the molecules.
C)a monomer with a double bond.
D)a monomer with a triple bond.
E)one or two monomers,each with one reactive group.

Question 46

The following polymer is called

A)teflon.
B)PVC.
C)polypropylene.
D)polyethylene.
E)polystyrene.

Question 47

What is the product of the reaction
CH₃CH(NH₂)CH₃ + CH₃CH₂C(O)OCH₃ $\rightarrow$

Question 48

Which of the following monomers is used to produce polystyrene?

A)CH(CH₃)CH₂
B)CHClCH₂
C)CH₂CH₂
D)CH(CN)CH₂
E)CH(C₆H₅)CH₂

Question 49

Fill in the missing compound in the following reaction.
CH₃CH₂Br + __________ $\rightarrow$ CH₃CH₂CN + NaI

Question 50

Which of the following monomers is used to produce Teflon?

A)CHClCH₂
B)CF₂CF₂
C)CH₂CH₂
D)CH(CH₃)CH₂
E)CH(CN)CH₂

Question 51

What is the product of the reaction
C₆H₅COCl + CH₃NH₂ $\rightarrow$

Question 52

The following polymer is called

A)polyester.
B)dacron.
C)teflon.
D)kevlar.
E)nylon-66.

Question 53

Which of the following would be attacked by an electrophilic reagent?

A)2 and 5 only
B)1 and 4 only
C)1,2,4,and 5
D)3 and 5
E)1 And 4 only

Question 54

The polymer that is formed from acrylonitrile is

A)teflon.
B)orlon.
C)cucite.
D)polystyrene.
E)PVC.

Question 55

All the following polymers are produced by addition polymerization except

A)polyethylene.
B)Dacron.
C)PVC.
D)polypropylene.
E)Teflon.

Question 56

What reactants could be used to synthesize CH₃CONH₂?

Question 57

Fill in the missing compounds or reagents in the following reaction scheme.
C₆H₅CHCH₂ + ______ $\rightarrow$ C₆H₅CH(Br)CH₃ + CH₃CH₂O^-Na⁺ $\rightarrow$ ________

Question 58

The structure of rubber,a polymer,is What is the formula of the monomer used to produce rubber?

A)(CH₃)₂CCHCH₃
B)CH₃CCCH₃
C)CH₂CCCH₂
D)CH₂C(CH₃)CHCH₂
E)CH₃CH(CH₃)CH₂CH₃

Question 59

The systematic name of CH₃CH₂COCH₃ is

A)2-butanone.
B)3-butanal.
C)methypropylether.
D)2-butanal.
E)3-butanone.

Question 60

What is the product of the reaction
CH₃CH₂CH₂Br + NaHS $\rightarrow$

Question 61

Fill in the missing reactants and products.

Question 62

Amines react with both carboxylic acids and acid chlorides to produce amides.

Question 63

What are the formulas of the monomers used to produce the nylon polymer shown below?

A)NH₂CH₂CH₂NH₂ and (COCl)-C₆H₄-(COCl)(substituents are para)
B)NH₂CH₂CH₂Cl and (COCl)-C₆H₄-(COOH)
C)HOOC-CH₂CH₂-COOH and NH₂-C₆H₄-NH₂ (substituents are para)
D)ClCH₂CH₂Cl and (COOH)-C₆H₄-(COOH)(substituents are para)
E)ClCH₂CH₂Cl and NH₂-C₆H₄-NH₂ (substituents are para)

Question 64

The primary structure of aspartame is This dipeptide is

A)Phe-Asp.
B)Trp-Glu.
C)Phe-Glu.
D)Tyr-Glu.
E)Tyr-Asn.

Question 65

Which of the following refers to the secondary structure of a protein?

A)Denaturation
B)( $\alpha$ helix)
C)Amino acid sequence
D)Disulfide linkages
E)Base pairs

Question 66

Which of the following polymers are addition polymers?

A)1,3,and 5
B)2 and 3
C)2 and 4
D)4 and 5
E)3 only

Question 67

Which of the following polymers are condensation polymers?

A)3 only
B)2 and 4
C)2 and 3
D)4 and 5
E)1,3,and 5

Question 68

Which of the following is a peptide bond?

A)(-C(O)O-)
B)(-CONH-)
C)(-C-NH-)
D)(-C=N-)
E)(-C(O)-)

Question 69

Complete hydrolysis of a hexapeptide yielded Arg,Tyr,Val,Phe,Cys.After partial hydrolysis,the fragments Tyr-Cys,Arg-Phe,Cys,Val-Arg,and Phe-Tyr were obtained.What are the possible sequences in the hexapeptide?

Question 70

What reactants would be used to synthesize the following compound? Choose from the following.

Question 71

The primary structure of a peptide is This peptide is

A)Tyr-Asn-Cys-Phe.
B)Tyr-Glu-Cys-Phe.
C)Phe-Asp-Cys-Tyr.
D)Phe-Glu-Met-Tyr.
E)Tyr-Asp-Met-Phe.

Question 72

If the base sequence along a portion of one strand of a double helix is CTACACG,the corresponding sequence on the other strand is

A)GATGTGC.
B)CUACACG.
C)TCGTGTC.
D)CTUCUCG.
E)CTACACG.

Question 73

Esters can be produced by a condensation reaction between acid halides and alcohols.If the acid halide CH₃COCl reacts with ethanol,which of the following is eliminated?

A)HCl
B)H₂O
C)OH^-
D)H₃O⁺

Question 74

Consider the reactions
CH₃CH₂CH₃ + Br₂/light $\rightarrow$ A
A + NaCN $\rightarrow$ B
Identify A and B.

Question 75

The typical amino acid,NH₂CHRCOOH,has pK_a1 and pK_a2 of 2.4 and 9.8,respectively.What is(are)the major species in an aqueous solution whose pH is 10?

Question 76

When amines condense with carboxylic acids,what molecule is eliminated?

Question 77

The $\alpha$ helix results from the pairing of specific bases by hydrogen bonding.Which pairs form hydrogen bonds?

A)AT and GC
B)AC and GC
C)GT
D)AT,GC,AC,and GT
E)AC

Question 78

How many hydrogen bonds are formed between T and A?

A)2
B)1
C)3
D)4

Question 79

In the reaction of CH₃CH₂COOH with CH₃NH₂,what molecule is eliminated?

Question 80

What reactants could be used to synthesize CH₃CH₂CH₂C(O)OCH₃?