Chp. 11-13 Exam Review

Question 1

What do you get when you oxidize secondary alcohol with PCC?

Answer 1

Ketone

Question 2

What is Markovnikov’s Rule?

Answer 2

* “The rich get richer”

* The carbon with the largest # of carbon atoms gets the X (halogen) or OH bind to it

Question 3

What is conjugation?

Answer 3

Sequence of alternating double or triple bonds.

Question 4

What are 5 common nucleophiles?

Answer 4

I-

Br-

Cl-

HS-

H2S

RSH

HO-

RO-

NC-

Question 5

What happens when secondary alcohol undergoes… a) KMnO4 b) H2CrO4 c) PCC

Answer 5

The secondary alcohol is converted to… a) Ketone b) Ketone c) Ketone

Question 6

What is oxidation?

Answer 6

1. Loss of electrons; 2. Adding an oxygen; 3. Adding an additional bond to the oxygen (eg. from single bonded oxygen, it becomes double bonded)

Question 7

What are the names of the molecules from left to right?

Answer 7

Ketone; aldehyde; carbocyclic acid

Question 8

What reagent can you use to convert an alkene to an epoxide?

Answer 8

MCPBA

Question 9

What is chromic acid?

Answer 9

H2CrO4

Question 10

What reagents can you use to reduce a ketone to a 2* alcohol?

Answer 10

NaBH4 or LAH

Question 11

What product do you get when you apply PCC on a 1* alcohol?

Answer 11

Aldehyde

Question 12

Are the following acids strong or weak? What are their pkas?

I-H

Br-H

Cl-H

SO3-H

HO3+

Answer 12

These are strong acids. Their pkas are…

I-H -11

Br-H -9

Cl-H -7

SO3-H -3

HO3+ -2

Question 13

What product do you get?

Answer 13

Question 14

What is this molecule?

Answer 14

Benzene

Question 15

What do you get when you oxidize a 1* alcohol with H2CrO4?

Answer 15

Carboxylic Acid

Question 16

What does aprotic mean?

Answer 16

The solvent does NOT have a proton on an electronegative atom.

Question 17

Are the following acids strong or weak? What are their pkas?

H20

1* alcohol

3* alcohol

NH3

Answer 17

These are weak acids. Their pkas are…

H20 15.7

1* alcohol 16

3* alcohol 18

NH3 38

Question 18

If the top row is a reactant, and the bottom row is the product, is this oxidation or reduction? Why?

Answer 18

Reduction. You are adding an H. (Gained electrons)

Question 19

What is the product if you use KMnO4, H2CrO4 or PCC with tertiary alcohol?

Answer 19

No Reaction

Question 20

What do you get when you oxidize primary alcohol with KMnO4?

Answer 20

Carboxylic Acid

Question 21

What product do you get if you reduce a carboxylic acid with NaBH4?

Answer 21

No Reaction

Question 22

What happens when primary alcohol undergoes… a) KMnO4 b) H2CrO4 c) PCC

Answer 22

The primary alcohol is converted to… a) Carboxylic acid b) Carboxylic acid c) Aldehyde

Question 23

Examples of polar aprotic solvents.

Answer 23

acetone, DMSO, DME and DMF

Question 24

When primary alcohol undergoes PCC, what happens?

Answer 24

It becomes an aldehyde.

Question 25

What are examples of reducing agents?

Answer 25

1) LiAlH4 (LAH); 2) NaBH4, H20; 3) H2, Ni; 4) Na, EtOH

Question 26

Is this oxidation or reduction? What are the reagents to get the products from top to bottom?

Answer 26

This is oxidation. KMnO4 H2CrO4 PCC

Question 27

What is a reduction?

Answer 27

Gain of electrons.

Question 28

What three reagents can you use to convert a 2\* alcohol to a ketone?

Answer 28

KMnO4 and H2CrO4 and PCC

Question 29

Does strong Acid have a weak conjugate base?

Answer 29

True

Question 30

What happens when tertiary alcohol undergoes... a) KMnO4 b) H2CrO4 c) PCC

Answer 30

What happens when tertiary alcohol undergoes... a) No reaction b) No reaction c) No reaction

Question 31

What do you get when you reduce a carboxylic acid with LAH? How about with NaBH4?

Answer 31

1\* alcohol; No Reaction

Question 32

What is the product from top to bottom?

Answer 32

Question 33

What mechanism is this? You have a tertiary, nucleophile, leaving group and a polar solven to stabilize the carbocation.

Answer 33

SN1

Question 34

This mechanism works for primary, maybe secondary; you need a strong nucleophile and leaving group; there is an inversion at the chirality center, need a polar solvent to dissolve nucleophile and it is favored by polar aprotic solvents.

Answer 34

SN2

Question 35

What is Hoffman Rule

Answer 35

\* Elimination yields the least substituted alkene \* use a bulky base such as tert-butoxide (t-BuOK) in tert-butyl alcohol (t-buOH).

Question 36

\* Favors substrates that can form stable carbocations. \* Bulky group \*Alcohols dehydrated follows this mechanism in 2\* and 3\* alcohols \* Favored by use of POOR NUCLEOPHILES (weak bases)

Answer 36

E1

Question 37

\* Uses a 2\* or 3\* alkyl halide is possible; \* HIgh temperature favors elimination over substitution \* Use EtONA/EtOH and t-BuOK/t-BuOH Zaitsev product \* Primary alcohols follow this mechanism or rearrangement \* H must be anti to leaving group

Answer 37

E2