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Z - Chem 2220 (S&T) Organic Chemistry II > Chapter 16 > Flashcards

Chapter 16 Flashcards

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1
Q

What is Formaldehyde?

A

H-(C=O)-H

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2
Q

What is Acetaldehyde?

A

H3C-(C=O)-H

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3
Q

What is Acetone?

A

H3C-(C=O)-CH3

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4
Q

What is Acetophenone?

A

Ph-(C=O)-CH3

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5
Q

What is Benzophenone?

A

Ph-(C=O)-Ph

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6
Q

What is Benzaldehyde?

A

Ph-(C=O)-H

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7
Q

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

A

-(C=O)-R

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8
Q

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

A

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

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9
Q

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

A

-carbaldehyde

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10
Q

How are dialdehydes named?

A

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

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11
Q

What is the suffix for ketones?

A

-one (to replace an -e suffix)

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12
Q

What is the structure for the common names of ketones?

A

alkyl alkyl ketone

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13
Q

How are diketones named?

A

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

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14
Q

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

A

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

ketone needs location number, aldehyde does not

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15
Q

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

A

the OH is a hydroxy substituent

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16
Q

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

A

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

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17
Q

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

A

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

18
Q

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

A

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

19
Q

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

A

Replace =O with R

Witting Reaction, The Addition of Ylides/Zwitter ions

20
Q

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

A

Replace =O with =NR, Imine

21
Q

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

A

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

22
Q

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

A

Replace =O with hydrogens, Wolff-Kishner Reduction

23
Q

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

A

Replace =O with two -OR, acetal

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

24
Q

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

A

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

25
Q

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

A

Replaces hydrogen with a single bond to a O-, produces free Ag

Tollen’s Test, Silver Mirror

26
Q

What is the effect of addition SOCl2 to alcohols?

A

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

27
Q

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

A

Replace =O with hydrogens, Clemmensen reduction

28
Q

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

A

Replaces =O with two -SEt, thioacetal

29
Q

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?

A

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

30
Q

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

A

Reduction to alkane, replaces the sulfur with hydrogen

31
Q

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-?

A

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.

32
Q

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

A

Replaces =O with =NNHPh

Phenylhydrazone

33
Q

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

A

Replaces =O with =NOH

Reactant is hydroxyl amine and product is oxime

34
Q

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

A

oxidize 1* with PCC or Pyridine/CrO3

35
Q

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

A

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

36
Q

How do you get ketones from alcohols

A

oxidize 2* with H2CrO4, PCC, or KMnO4

37
Q

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

A

LiAlH4 or NaBH4 or Na/EtOH

38
Q

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

A

Grignard(RMgX) or RLi

39
Q

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

A

LiAlH4 or NaBH4

40
Q

What reagents will oxidize aldehydes to carboxylic acids?

A

(with acid)

KMnO4/OH- or Ag2O/OH

Z - Chem 2220 (S&T) Organic Chemistry II (12 decks)

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