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Organic Chemistry > 9 > Flashcards

9 Flashcards

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1
Q

Alcohol formula

A

R-O-H

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2
Q

Ether formula

A

R-O-R

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3
Q

Epoxide formula

A

three membered ring with an O in it

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4
Q

In an unsymmetrical ether the R groups are ______

A

different

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5
Q

an enol group is an sp2 hybridzied alcohol that is/isn’t attached to a ring

A

isn’t

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6
Q

A phenal is/is not attatched to a ring

A

is

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7
Q

In a ring -OH is labeled _

A

1

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8
Q

An epoxide is a special type of _____

A

ether

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9
Q

The C-O-C bon angle for an epoxide is __ degrees

A

60

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10
Q

Epoxides have ____ ______, making them more reactive than other ethers

A

angle strain

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11
Q

Alcohols and ethers have a _____ geometry

A

bent

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12
Q

In a carbon ring, the carbon bearing OH is labeled _

A

1

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13
Q

What does Isopropyl alcohol look like

A
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14
Q

Two alcohols changes the suffix to _____

A

diols

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15
Q

Compounds with three hydroxy groups are called ____

A

triols

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16
Q

If you had a methyl to the left of an ether and sec-butyl to the right of an ether, the ehter would be called:

A

Sec-butyl methyl ether

(b is earlier than m)

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17
Q

If you had an ethyl on both sides of an ether it would be called:

A

diethyl ether

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18
Q

In an either substituent (such as CH3O-) you replace the -yl with ____

A

-oxy

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19
Q

CH3O-

CH3CH2O-

(CH3)3C-O-

A

Methoxy

Ethoxy

Tert-butoxy

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20
Q

Name as an alekene oxide

A

2-methyl-1,2-epoxypropane

21
Q

R-CH2-OH —->R3C-OH

To the right____

To the left_____

A

Increasing steric hinderence to the right

Increasing ability to hydrogen bond to the left

22
Q

Alcohols, ether,s and epoxides having less than or equal to five C’s are H2O insoluable/soluable

while more means they H2O insoluable/soluable

A

soluable

insoluable

23
Q

A crown ether acts as a host to a__

A

cation which is called the guest

24
Q

Crown ethers can be used in ___ reactions

A

SN

25
Q

Ethers can be easily prepared in ___ reactions

A

SN2

26
Q

Alkooxides are formed through ____ chemistry

A

acid base

27
Q

Epoxides can be synthesized from_____

A

halohydrins

28
Q

-OH group of alcohols are a great/poor leaving group

A

poor

29
Q

So -OH must be converted into a better leaving group for alcohol SN reactions.

R-OH+H-CL–>R-OH2+Cl-

A
30
Q

Dehydration rections are the elimination of

A

H-O-H groups

31
Q

Dehydrations are carried out by using ____ in the present of an _____ base

A

H2SO4

Amine

32
Q

More substituated alcohols dehydrate slower/faster

A

faster (3 degree is best)

33
Q

The more substituated alkene is the major/minor product when a mixture of cons isomers is possible

A

major

34
Q

Reactions of Alcohol: Dehydration

Step 1

Step 2

Step 3

A

The O atom is protanated (-OH to -OH2) though sulferic acid

The C-O bond is broken forming a carbocation and H2O

Base romoves carbocations extra H in elimination

35
Q

Reactions of Alcohols: dehrydration

E1 dehydration of 2 and 3 degree alcohols with acid gives clean elimination without ____ products

E1 dehydration of alcohols is more synthetically useful than E1 dehydrohalogenation of alkyl halides

A

SN1

36
Q

Reactions of alcohols dehydration 1 degree*

Step 1

Step 2

A

The O atom is protonated with H2SO4

The C-H and C-O bonds are broken and the pie bond is formed

37
Q

Alcohol dehydration is thermodynamically favorable/unfavorable

A

unfavorable (endothermic)

38
Q

Despite being endorthermic, you can use ____ to remove product taking advantage of le chatliers principle

A

distillation

39
Q

Unstable carbocations rearrange to more stable carbocations

The migrating group moves in a ___ shift

A

1,2

40
Q

Movement of H is a 1,2-_____ shift

A

hydride

41
Q

Movement of an alkyl group is a 1,2-____ shift

A

alkyl

42
Q

A 1,2 methyl shift is a 4 step affiar

step 1 and 2

Step 3

Step 4

A

Formation of a 2 degree carbocation (-OH takes proton form H2SO4 then is eliminated as H2O)

Step 3 rearrangement of the carbocation by a 1,2-CH3 shift

Loss of proton to form the pie bond (picked off by HSO4-)

43
Q

Reactions of Alcohols: Dehydration

Rearrangments may occur whenever a carbocation is formed as a reactive intermediate (and the carbon the H is moving to is less stable as to equalize stability)

A

absorb

44
Q

Some alcohols ______ in the presence of strong acid

A

decompose

45
Q

Acommon reagent for alcohol decomposition is ____ or ____

A

POCL3 or pyradine

46
Q

Dehydration of alcohol (E2 elimination)

Steps 1 and 2

Step 3

A

Conversion of OH to a good leaving group (POCl3 attatches to OH and loses a Cl, then pyradine takes an H and O’s charge is restored)

The C-H and C-O bonds are broken and the pie bond is formed. The end leaving group is -OPOCl2 + a + charged pyradine

47
Q

Conversion of alcohols to alkyl halides

Must use H-X archetype because -OH is a poor leaving group. The H forms H2O and R attatches to X

A

Proton transfer shit absorb

48
Q

1 degree -OH have faster/slower rates of reactions with HX than 3 degree -OH

A

slower

49
Q

Conversionof Alcohols to Alkyl Halides

A

Organic Chemistry (9 decks)

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