Carbonyls (Ch 13-16)

Question 1

Aldehydes undergo Nucleophilic _______ reactions.

Answer 1

Addition

Question 2

Ketones undergo Nucleophilic ______ reactions.

Answer 2

Addition

Question 3

Carbonyl Compounds with LGs undergo Nucleophilic ________ Reactions

Answer 3

Substitution

Question 4

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

Answer 4

Addition then Elimination

Question 5

Which is more reactive: Aldehydes or Ketones?

Why?

Answer 5

Aldehydes

Because aldehydes are less crowded and less stable than ketones.

Question 6

Two Main Steps of Nucleophilic Addition

Answer 6

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

Question 7

Nucleophilic Addition of Aldehydes and Ketones forms _____.

Answer 7

Alcohols

Question 8

What are the 2 Steps of Nucleophilic Substitution Mechanism?

Answer 8

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

Question 9

Which Carboxylic Acid has the best LG?

Answer 9

Acid Chlorides

Question 10

Carboxylic Acid Derivative with Worst LG

Answer 10

Amides

Question 11

Which 2 compounds have LG of similar Basicity?

Answer 11

Esters
Carboxylic Acids

Question 12

2 Ways to ID Oxidation Reaction

Answer 12

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

Question 13

2 ways to ID reduction rxns

Answer 13

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

Question 14

Why are Carbolxylic Acid Derivatives Called Carboxylic Acid Derivatives?

Answer 14

A hydrolysis rxn results in a carboxylic acid

Question 15

2-ethylpentanal is what type of molecule?

Answer 15

aldehyde

-al suffix
C1 is the CHO carbon

Question 16

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

Answer 16

The chain connected directly to the O is the alkyl.

The chain with the carbonyl carbon is the acyl group.

Question 17

How to Name an Ester

Answer 17

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

Question 18

Alcohol + Carboxylic Acic –>

Answer 18

Ester

Question 19

What type of molecule is propyl 3-methylbutanoate?

Answer 19

Ester

Question 20

-OCH3

Answer 20

methoxy group

Question 21

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

Answer 21

Amide

Question 22

Namingng an Amide

Answer 22

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

Suffix -amide

Question 23

2, 2-dimethylcyclopentanone is what type of molecule?

Answer 23

Ketone

Question 24

suffix -one designates a _____

Answer 24

Ketone

Question 25

-al designates a _______

Answer 25

Aldehyde

Question 26

-oate designates a ____.

Answer 26

Ester

Question 27

-oic acid designates a _____.

Answer 27

Carboxylic Acid

Question 28

-oyl chloride designates a ______.

Answer 28

Acid Chloride

Question 29

Designates an Aldehyde

Answer 29

-al

Question 30

Designates and Ester

Answer 30

-oate

Question 31

Designates a Carboxylic Acid

Answer 31

-oic acid

Question 32

Designates an Acid Chloride

Answer 32

-oyl chloride

Question 33

Designates a Ketone

Answer 33

-one

Question 34

Acetal

Answer 34

2 Ethers on the Same Carbon (2 -OR groups on same carbon)

Question 35

Hemiacetal

Answer 35

An Alcohol and an Ether Group attached to the same Carbon (-OH and -OR group on same carbon)

Question 36

Hemiketal AKA

Answer 36

Hemiacetal

Question 37

Ketal AKA

Answer 37

Acetal

Question 38

NaBH4 acid or base strong or weak

Answer 38

weak base

Question 39

LiAlH4 acid or base strong or weak

Answer 39

strong base

Question 40

alkene --> alkane reducing reagent

Answer 40

H2/Pt

Question 41

Ketone --> Alcohol reducing reagent

Answer 41

H2/Pd-C

Question 42

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

Answer 42

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

Question 43

2 Reagents that can be used to reduce Aldehydes to Alcohols

Answer 43

NaBH4 LiAlH4

Question 44

Reagent used to Reduce Ketones to Alcohols

Answer 44

NaBH4

Question 45

Reagent used to Reduce Acid Chloride to Alcohol

Answer 45

LiAlH4 *Notes: Goes through a aldehyde intermediate

Question 46

Reagent used to Reduce Acid Chloride to Aldehyde

Answer 46

LiAl-tritertbutoxy

Question 47

Reagent used to Reduce Ester to Alcohol

Answer 47

LiAlH4

Question 48

Reagent used to Reduce Ester to Aldehyde

Answer 48

DIBAL-H