Chapter 16

Question 1

What is Formaldehyde?

Answer 1

H-(C=O)-H

Question 2

What is Acetaldehyde?

Answer 2

H3C-(C=O)-H

Question 3

What is Acetone?

Answer 3

H3C-(C=O)-CH3

Question 4

What is Acetophenone?

Answer 4

Ph-(C=O)-CH3

Question 5

What is Benzophenone?

Answer 5

Ph-(C=O)-Ph

Question 6

What is Benzaldehyde?

Answer 6

Ph-(C=O)-H

Question 7

What is an Alkanoyl Group? (also called an acyl group)

Answer 7

-(C=O)-R

Question 8

What are the two suffixes commonly used aldehyde nomenclature? (one short and one long)

Answer 8

-al (to replace an -e suffix) and (parent chain name)-aldehyde

Question 9

What is the suffix if a -CHO (aldehyde group) is attached to a ring?

Answer 9

-carbaldehyde

Question 10

How are dialdehydes named?

Answer 10

omit location number (aldehydes are assumed to be on the ends of the compound) and change the ending to -dial

Question 11

What is the suffix for ketones?

Answer 11

-one (to replace an -e suffix)

Question 12

What is the structure for the common names of ketones?

Answer 12

alkyl alkyl ketone

Question 13

How are diketones named?

Answer 13

both carbonyls require a location number and change the suffix to Dione

if in.a ring, the -e suffix remains and is immediately before the Dione suffix

Question 14

How are compounds containing both an aldehyde and a ketone named?

Answer 14

compound is named as an aldehyde and the ketone is named as an oxo substituent

ketone needs location number, aldehyde does not

Question 15

How are aldehydes and ketones named when there is an OH in the same compound?

Answer 15

the OH is a hydroxy substituent

Question 16

How are cyanohydrins C(-OH)(≣N) produced?

Answer 16

Add NaCN to an aldehyde or a ketone. The =O is replaced with a -OH and -C(triple bond)N

Question 17

What is the effect of the addition of HCl, H2O, and heat to a cyanohydrin C(-OH)(≣N)?

Answer 17

Produces a carboxylic acid with a double bond on the more substituted side

Question 18

What is the effect of the addition of LiAlH4 and H2O to a cyanohydrin C(-OH)(≣N)?

Answer 18

Replaces -C(triple bond)N with -CNH2, two hydrogens. (adds four hydrogens total)

Question 19

What is the effect of the addition of R-PPh3 to an aldehyde or a ketone? Bonus: What is this reaction called?

Answer 19

Replace =O with R

Witting Reaction, The Addition of Ylides/Zwitter ions

Question 20

What is the effect of adding a primary amine to an aldehyde or ketone? Bonus: What is the product called?

Answer 20

Replace =O with =NR, Imine

Question 21

What is the effect of adding a secondary amine to an aldehyde or ketone? Bonus: What is the product called?

Answer 21

Replace =O with -NR2 and double bond on more substituted side, Enamine

Question 22

What is the effect of the addition of N2H4/Oh/heat to an aldehyde or ketone? Bonus: What is this reaction called?

Answer 22

Replace =O with hydrogens, Wolff-Kishner Reduction

Question 23

What is the effect of the addition of alcohols to aldehydes or ketones? Bonus: What is the product called?

Answer 23

Replace =O with two -OR, acetal

Note: Also produces an intermediate of a hemiacetal, where one of the -OR groups is an -OH

Question 24

What is the effect of the addition of dialcohols to aldehydes or ketones?

Answer 24

Replace =O with two single bonds to the ends of an ORO (one bond to each O, produces a cyclic compound)

Question 25

What is the effect of the addition of Ag(NH3)2 to an aldehyde? Bonus: What is this reaction called?

Answer 25

Replaces hydrogen with a single bond to a O-, produces free Ag Tollen's Test, Silver Mirror

Question 26

What is the effect of addition SOCl2 to alcohols?

Answer 26

Forms alkyl chlorides with all alcohol except for 3* (replaces OH with Cl)

Question 27

What is the effect of the addition of Zn/Hg/HCl to an aldehyde or ketone? Bonus: What is this reaction called?

Answer 27

Replace =O with hydrogens, Clemmensen reduction

Question 28

What is the effect of the addition of EtSH to an aldehyde or ketone? Bonus: What is the product called?

Answer 28

Replaces =O with two -SEt, thioacetal

Question 29

What is the effect of the addition of HS-R-SH to an aldehyde or ketone? Bonus: What is the name of the product and the name of the reactant?

Answer 29

Cyclic thioacetal, replaces =O with single bonds to the ends of a SRS, reactant called a dithiol

Question 30

What is the effect of adding H2 and RaNi (Raney nickel) to a thioacetal (compound with -SR groups)?

Answer 30

Reduction to alkane, replaces the sulfur with hydrogen

Question 31

What is the effect of the addition of H2NNH2 to an aldehyde or ketone? Bonus: What is the name of the product and the name of the reactant? What happens when combined with OH-?

Answer 31

Replaces =O with =N-NH2 Reactant is hydrazine and product is hydrazone If the reaction is combined with OH- it just replaces the =O with two hydrogens.

Question 32

What is the effect of the addition of H2NNHPh to an aldehyde or ketone? Bonus: What is the product called?

Answer 32

Replaces =O with =NNHPh | Phenylhydrazone

Question 33

What is the effect of the addition of H2NOH to an aldehyde or ketone? Bonus: What are the product and reactant called?

Answer 33

Replaces =O with =NOH | Reactant is hydroxyl amine and product is oxime

Question 34

How do you get aldehydes from alcohols? Give some reagents?

Answer 34

oxidize 1* with PCC or Pyridine/CrO3

Question 35

How do you get aldehydes from carboxylic acids, esters, and acyl chlorides?

Answer 35

reduction with NaBH4, LiAlH(OtBu)3/Et2O,

Question 36

How do you get ketones from alcohols

Answer 36

oxidize 2* with H2CrO4, PCC, or KMnO4

Question 37

What are some reagents that will reduce aldehydes to alcohols without adding extra R groups?

Answer 37

LiAlH4 or NaBH4 or Na/EtOH

Question 38

What are reagents that will reduce aldehydes or ketones to alcohols and add extra R groups?

Answer 38

Grignard(RMgX) or RLi

Question 39

What are some reagents that will reduce ketones to alcohols without adding extra R groups?

Answer 39

LiAlH4 or NaBH4

Question 40

What reagents will oxidize aldehydes to carboxylic acids?

Answer 40

(with acid) | KMnO4/OH- or Ag2O/OH