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CHEM 246 > EXAM 3 > Flashcards

EXAM 3 Flashcards

1
Q

What does aldehyde reacting with NaBH4 and H3O+ yield?

A

no rxn

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2
Q

What does aldehyde reacting with LiAlH4 and H3O+ yield?

A

C bonded to R, OH, and 2H

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3
Q

What does ketone reacting with NaBH4 and H3O+ yield?

A

C bonded to R, R’, OH, and H

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4
Q

What does ketone reacting with LiAlH4 and H3O+ yield?

A

C bonded to R, R’, OH, and H

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5
Q

What does carboxylic acid reacting with LiAlH4 and H3O+ yield?

A

C bonded to OH and R

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6
Q

What does an ester reacting with LiAlH4 and H3O+ yield?

A

C bonded to OH and R + HOR’

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7
Q

What yields when you react RMgBr with R’ containing double bonded O and H3O+?

A

R-R’ now containing OH instead of double bonded O

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8
Q

What yields when you react an anhydride with R’‘OH?

A

ester and carboxylic acid

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9
Q

What yields when you react an anhydride with RNH2?

A

amide and carboxylic acid

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10
Q

What yields when you react an anhydride with RMgBr?

A

primary alcohol

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11
Q

What yields when you react an anhydride with [H]?

A

primary alcohol

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12
Q

Describe alpha substitution reaction

A

H breaks off carbon next to double bonded O and goes to base, break double bonded O to yield alkene in middle, break this double bond to add E to that C and reform double bonded O

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13
Q

What yields when you react aldehyde with CrO3?

A

carboxylic acid

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14
Q

What yields when you react aldehyde with NaOH?

A

deprotonated carboxylic acid

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15
Q

What happens when you react a gringard reagent with carbon dioxide and H3O+?

A

carboxylic acid

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16
Q

What happens when you react R-C triple bonded with KOH and H3O+?

A

carboxylic acid

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17
Q

What happens when you react R-C-X with NaCN?

A

R-C-CN

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18
Q

What happens when you react R-C-CN with LiAlH and H3O+?

A

C-C-NH2

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19
Q

What happens when you react R-C-CN with KOH and H3O+?

A

R-carboxylic acid

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20
Q

What happens when you react carboxylic acid with SOCl3?

A

replace OH with Cl

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21
Q

What happens when you react carboxylic acid with PBr3?

A

replace OH with Br

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22
Q

What yields when you react R-C=O bonded to good LG with NH3?

A

replace good leaving group with NH2

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23
Q

What yields when you react R-C=O bonded to good LG with R’OH?

A

ester

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24
Q

What yields when you react R-C=O bonded to good LG with H2O?

A

carboxylic acid

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25
Q

What yields when you react R-C=O bonded to good LG with carboxylic acid?

A

anyhydride

26
Q

What yields when you react R-C=O bonded to good LG with DiBAlH?

A

aldehyde

27
Q

What yields when you react R-C=O bonded to good LG with LiAlH4 and H3O+?

A

primary alcohol

28
Q

What yields when you react R-C=O bonded to good LG with R’MgX and H3O+?

A

C bonded to OH, R and 2R’

29
Q

What yields when you react R-C=O bonded to good LG with (Cu2R’)Li and H3O+?

A

C bonded to R, R’, and double bonded O

30
Q

What yields when you react primary alcohol with Ness Martin?

A

aldehyde

31
Q

What yields when you react ester with LiAlH4?

A

primary alcohol

32
Q

What yields when you react ester with DiBAlH

A

aldehyde

33
Q

What yields when you react ester with Grignard?

A

C bonded to OH, R, 2R’

34
Q

What yields when you react ester with R’2CuLi?

A

C bonded to R, R’, and double bonded O

35
Q

What yields when you react 2propanol with Dess Martin?

A

ketone

36
Q

What yields when you react aldehyde with nucleophile and HA?

A

C bonded to OH, R, H, and Nu

37
Q

What yields when you react aldehyde with NuH2?

A

C bonded to R, H, and double bonded Nu

38
Q

How do you form imine?

A

double bonded O and RNH2

39
Q

How do you form examine?

A

double bonded O and R2NH2

40
Q

What is an imine?

A

carbon molecule with double bond connected to N

41
Q

What is enamine?

A

alkene with N single bonded to it

42
Q

What happens when you react a secondary alcohol with CrO3?

A

replace alcohol with double bonded O

43
Q

What happens when you react primary alcohol with CrO3?

A

form carboxylic acid

44
Q

What happens when you react secondary alcohol with Dess Martin?

A

replace alcohol with double bonded O

45
Q

What happens when you react primary alcohol with Dess Martin?

A

form aldehyde

46
Q

What happens when you react ketone with NH2NH2 and KOH?

A

replace double bonded O with 2 Hs

47
Q

What happens when you react ketone with 2ROH and H+?

A

replace double bonded O with 2 OR groups

48
Q

Describe Witting Rxn

A

switch O on double bond (stable molecule) with group bonded to R3P (less stable molecule)

49
Q

How do you synthesize a Witting Rxn?

A

use nBuLi to bond group on good LG to R3P

50
Q

What happens when you react ketone with ethanediol (?) and H+?

A

replace OHs with O and connect them on top of the other 2 Cs (COUNT CARBONS!)

51
Q

What happens when you react -oate molecule with ethanediol (?), H+, LiAlH4, H2O?

A

replace ester with alcohol (COUNT CARBONS!)

52
Q

What kind of addition to you do with Grignard? Where should the double bond be?

A

1,2 … double bond on ring

53
Q

What kind of addition to you do with (CuR2)Li? Where should the double bond be?

A

1,4 … double bond on O

54
Q

What yields when you react C=C-C=O with NuH?

A

Nu-C-C=O

55
Q

What is the suffix on carboxylic acid?

A

-oic acid

56
Q

What is the suffix on C-C-NH2 with double bonded O on center C?

A

-amide

57
Q

What is the suffix on C-C-X with double bonded O on center C?

A

-yl halide

58
Q

What is the suffix on asymmetrical ester?

A

-oate

59
Q

What is the suffix on R-C-R’ with double bonded O on center C?

A

-one

60
Q

What is the suffix on C-C-H with double bonded O on center C?

A

-al

61
Q

What is the suffix on ester with single bonded O replaced by S?

A

-thioate

62
Q

What is the suffix on symmetrical ester?

A

-oic anhydride

CHEM 246 (7 decks)

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