Carbonyls (Ch 13-16) Flashcards

1
Q

Aldehydes undergo Nucleophilic _______ reactions.

A

Addition

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2
Q

Ketones undergo Nucleophilic ______ reactions.

A

Addition

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3
Q

Carbonyl Compounds with LGs undergo Nucleophilic ________ Reactions

A

Substitution

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4
Q

A Nucleophilic Substitution Reaction is composed of which 2 types of reactions?

A

Addition then Elimination

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5
Q

Which is more reactive: Aldehydes or Ketones?

Why?

A

Aldehydes

Because aldehydes are less crowded and less stable than ketones.

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6
Q

Two Main Steps of Nucleophilic Addition

A
  1. Nucleophilic Attack of the carbonyl carbon
  2. Protonation of the -O to form -OH
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7
Q

Nucleophilic Addition of Aldehydes and Ketones forms _____.

A

Alcohols

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8
Q

What are the 2 Steps of Nucleophilic Substitution Mechanism?

A
  1. Nucleophilic Attack of the Carbonyl C
    (Moved the Double Bond e- onto the O)
  2. the pi bond is reformed and Z comes off as a LG
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9
Q

Which Carboxylic Acid has the best LG?

A

Acid Chlorides

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10
Q

Carboxylic Acid Derivative with Worst LG

A

Amides

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11
Q

Which 2 compounds have LG of similar Basicity?

A

Esters
Carboxylic Acids

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12
Q

2 Ways to ID Oxidation Reaction

A

Increase in # of C-Z bonds
Decrease in # of C-H bonds

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13
Q

2 ways to ID reduction rxns

A

Decrease in # of C-Z bonds
Increase in # of C-H bonds

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14
Q

Why are Carbolxylic Acid Derivatives Called Carboxylic Acid Derivatives?

A

A hydrolysis rxn results in a carboxylic acid

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15
Q

2-ethylpentanal is what type of molecule?

A

aldehyde

-al suffix
C1 is the CHO carbon

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16
Q

When naming an ester, which side is the alkyl group and which side is the acetyl group?

A

The chain connected directly to the O is the alkyl.

The chain with the carbonyl carbon is the acyl group.

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17
Q

How to Name an Ester

A

1) Name the Alkyl Group
2) Name the Acyl Group
3) Suffix -oate

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18
Q

Alcohol + Carboxylic Acic –>

A

Ester

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19
Q

What type of molecule is propyl 3-methylbutanoate?

A

Ester

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20
Q

-OCH3

A

methoxy group

21
Q

What type of molecule is 3-methoxy-N-methylbutanamide?

A

Amide

22
Q

Namingng an Amide

A

Specify which C or N substituents are attached to. C1 is the Carbonyl Carbon.

Suffix -amide

23
Q

2, 2-dimethylcyclopentanone is what type of molecule?

A

Ketone

24
Q

suffix -one designates a _____

A

Ketone

25
Q

-al designates a _______

A

Aldehyde

26
Q

-oate designates a ____.

A

Ester

27
Q

-oic acid designates a _____.

A

Carboxylic Acid

28
Q

-oyl chloride designates a ______.

A

Acid Chloride

29
Q

Designates an Aldehyde

A

-al

30
Q

Designates and Ester

A

-oate

31
Q

Designates a Carboxylic Acid

A

-oic acid

32
Q

Designates an Acid Chloride

A

-oyl chloride

33
Q

Designates a Ketone

A

-one

34
Q

Acetal

A

2 Ethers on the Same Carbon

(2 -OR groups on same carbon)

35
Q

Hemiacetal

A

An Alcohol and an Ether Group attached to the same Carbon

(-OH and -OR group on same carbon)

36
Q

Hemiketal AKA

A

Hemiacetal

37
Q

Ketal AKA

A

Acetal

38
Q

NaBH4

acid or base
strong or weak

A

weak base

39
Q

LiAlH4

acid or base
strong or weak

A

strong base

40
Q

alkene –> alkane

reducing reagent

A

H2/Pt

41
Q

Ketone –> Alcohol

reducing reagent

A

H2/Pd-C

42
Q

H2/Pd-C will reduce a _____ before ______.

A

H2/Pd-C will reduce an alkene to alkane before reducing =O (ketone) to -OH (alcohol)

43
Q

2 Reagents that can be used to reduce Aldehydes to Alcohols

A

NaBH4
LiAlH4

44
Q

Reagent used to Reduce Ketones to Alcohols

A

NaBH4

45
Q

Reagent used to Reduce Acid Chloride to Alcohol

A

LiAlH4

*Notes: Goes through a aldehyde intermediate

46
Q

Reagent used to
Reduce Acid
Chloride to Aldehyde

A

LiAl-tritertbutoxy

47
Q

Reagent used to Reduce Ester to Alcohol

A

LiAlH4

48
Q

Reagent used to Reduce Ester to Aldehyde

A

DIBAL-H

49
Q
A