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O Chem II CSCC > Alcohols > Flashcards

Alcohols Flashcards

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1
Q

why do alcohols have relatively high boiling points?

A

Because they have london dispersion forces AND dipole: dipole forces AND hydrogen bonding

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2
Q

what do you call it when you do rxns to an alcohol that already exists: oxidation or reduction?

A

oxidation

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3
Q

what do you call it when you’re trying to create an alcohol from and aldehyde or ketone or COOH or ester: oxidation or reduction?

A

reduction

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4
Q

what 4 things can you reduce in order to make an alcohol?

A

aldehyde or ketone or COOH or ester

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5
Q

what are the 4 types of rxns you can do to make alcohols?

A

substitution, reduction, addition, gringard

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6
Q

what is PCC sometimes seen with in oxidation rxns?

A

CH2Cl2 dichloromethane

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7
Q

what is a carbonyl?

A

carbon atom double-bonded to an oxygen atom: C=O

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8
Q

what is an epoxide?

A

a cyclic ether with a three-atom ring.

This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers.

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9
Q

what is a ketone?

A

a ketone is a functional group with the structure R₂C=O, where R can be a variety of carbon-containing substituents.

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10
Q

what is an ester?

A

chemical compound derived from an acid in which at least one –OH group is replaced by an –O–alkyl group.

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11
Q

what is this functional group?

A

alhedyde

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12
Q

what is an alkyl group?

A

an alkane missing one hydrogen

exp methYL instead of methANE

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13
Q

what is an aldehyde?

A

carbon atom shares a double bond with an oxygen atom, a single bond with a hydrogen atom, and a single bond with another atom or group of atoms

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14
Q

what is this functional group?

A

carboxyllic acid

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15
Q

what is this functional group?

A

epoxide

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16
Q

what is this functional group?

A

ester

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17
Q

what is this functional group?

A

ketone

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18
Q

what is the oxidation sequence when you use a weak oxidizer (like PCC) with a primary alcohol?

A

alcohol to aldehyde

stops short of progressing from aldehyde to carboxyllic acid

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19
Q

what is the oxidation sequence when you use a weak oxidizer (like PCC) with a secondary alcohol?

A

alcohol to ketone.

That’s it.

20
Q

what is the oxidation sequence when you use a strong oxidizer with a tertiary alcohol?

A

no rxn

21
Q

what is the reduction sequence when you use a strong reducer with a carboxyllic acid????

A

carboxyllic acid to aldehyde to primary alcohol????

22
Q

how can you tell how acidic an alcohol is?

A

look as the stregnth/pka value of its conjugate base

pka table on p 471 in textbook

23
Q

what is the reduction sequence when you use a strong reducer with a ketone?

A

ketone to secondary alcohol

24
Q

what is the reduction sequence when you use the strong reducer LiAlH4 with a ketone?

A

ketone goes to secondary alcohol

25
Q

what is the reduction sequence when you use the strong reducer LiAlH4 with a aldehyde?

A

aldehyde goes to primary alcohol

26
Q

what is the reduction sequence when you use the strong reducer LiAlH4 with a Carboxyllic acid?????

A

the COOH gets deprotonated????

27
Q

what is the reduction sequence when you use the strong reducer LiAlH4 with a ester?

A

ester gets cleaved into 2 alcohols

28
Q

what is the reduction sequence when you use the mild reducer NaBH4 with a ketone?

A

ketone goes to 2o alcohol

29
Q

what is the reduction sequence when you use the mild reducer NaBH4 with a aldehyde?

A

aldehyde goes to primary alcohol

30
Q

what is the reduction sequence when you use H2/Pt as a reducer?

A

the same as the other reducers, except it will also reduce any other pi bonds (e.g. C=C or C triple bond C)

31
Q

what does H2/Pt reduce C=C to?

A

C-C

32
Q

Sometimes the alcohols you’re reducing also have C triple bond C in them. What reagents do you need to reduce the C triple bond C to a CIS C=C?

A

H2/Lindler’s catalyst

33
Q

what does H2/Pt reduce C=O to?

A

C-OH

34
Q

what is an alkane?

A

a cabon completely saturated with hydrogens.

Has no pi bonds.

35
Q

how can you tell if an alcohol will likely be soluable in water?

A

if it has 5 or fewer carbons for every OH group, it will likely be soluable in water

36
Q

how can you tell how acidic a given alcohol is?

A

by looking at the pka of its conjugate base (from the table on p. 471 in the book)

or if you’re extra, compare the conjugate according to ARIO (atom, induction, resonance, and orbital hybridization.)

37
Q

do strong acids have high pka values or low pka values?

A

low

38
Q

what is so special about Grignard reagents?

A

they let you use carbons as nucleophiles

39
Q

where does the Mg fit into a grignard reagent?

A

Between the R group and the leaving group

exp. R-Mg-Cl

40
Q

where/how does the electrophile get protonated in the last step of a grignard rxn?

A

the second, water workup step of the rxn

41
Q

what is an alkoxide ion?

A

the conjugate base of an alcohol

42
Q

what is a counterion?

A

positively charged ions that accompany negatively charged bases

exp. Li+ is the counterion to OH-, which started as LiOH

43
Q

what are 3 weak nucleophiles you can use when making an alcohol via SN1 rxn?

A

CH3OH, H2O, and CH3SH

44
Q

which reagent can do rearrangement when you use it to make Markonikov alcohols: hydration or mercuration?

A

hydration

45
Q

Sometimes the alcohols you’re reducing also have C triple bond C in them. What reagents do you need in order to reduce the C triple bond C to a TRANS C=C?

A

Na/NH3

46
Q

Sometimes the alcohols you’re reducing also have C triple bond C in them. What reagents do you need in order to reduce the C triple bond C directly down to a C-C?

A

H2/Pt

47
Q

when you attack an alkyl halide with a grignard, does the alkyl halide kick off any leaving groups?

A

no

O Chem II CSCC (14 decks)

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