Chem3 - Oxygen Rxns

Question 1

Carboxylic acids typically do NOT undergo

Answer 1

nucleophilic addition

Question 2

what is a nucleophile?

Answer 2

attacks, donates electrons (lewis base), usually strong baseshigher electronegativity=decreased nucleophilicity

Question 3

what is the leaving group?

Answer 3

what is kicked off when the nucleophile attacks, definied by its stability alone or in solution. usually a weaker base

Question 4

alcohol

Answer 4

R-OH, H bonds, increases BP, can act as a nucleophile and a leaving group

Question 5

what is the function of a tosylate?

Answer 5

has a benzne ring, usually used to protect alcohols

Question 6

what is a mesylate?

Answer 6

usually used as a protecting group, has no benzene ring

Question 7

ether

Answer 7

R-O-R,can H bond but is relatively non reactive

Question 8

what is an electrophile?

Answer 8

gets attacked, usually with + charge.carbonyls common

Question 9

aldehydes and ketones being attacked can produce a ____ mixture

Answer 9

racemic

Question 10

what does stereoselective mean?

Answer 10

prefers R or S

Question 11

what does stereospecific mean?

Answer 11

100% or 0% of an isomer formed

Question 12

acid halide+RCOOH=

Answer 12

anyhdride

Question 13

acid halide+water=

Answer 13

COOH

Question 14

acid halide+ROH=

Answer 14

ester

Question 15

acid halide+RNH2=

Answer 15

amide

Question 16

what is the leaving group on an anhydride?

Answer 16

a carboxylate (R-COO-)

Question 17

what is transesterification?

Answer 17

one alkoxy group is substituted for another

Question 18

what is a lactone?

Answer 18

formed by intramolecular cyclization

Question 19

amides are the least reactive carbonyl, T/F

Answer 19

T

Question 20

what is a lactam?

Answer 20

cyclic amide

Question 21

do aldehydes and ketones have a leaving group?

Answer 21

no

Question 22

what does the kinetic enolate form during tautomerization?

Answer 22

least substituted alkene with lower Ea

Question 23

what does the thermodynamic enolate form?

Answer 23

most substituted alkene

Question 24

what is the produce of an aldhyde and a ketone reacting?

Answer 24

a hemiacetal

Question 25

imine=? enamine=?

Answer 25

C=N-RHC=C-NRR

Question 26

NABH4 and LiAH4(LAH) are

Answer 26

reducing agents that reduce ketones and aldehydesonly LAH reduces COOH, esters, & acetates

Question 27

cyanohydrin?

Answer 27

CN-, attacks carbonyl and produces a COOH when exposed to acid+water

Question 28

how many bonds can P form?

Answer 28

5

Question 29

what is oxidation?

Answer 29

increase in H bonds to O or X, loss of CH bonds

Question 30

what is reduction?

Answer 30

increase in H bonds or R groups, loss of O or X bonds

Question 31

what is Oxygens typical oxidation state?

Answer 31

-2

Question 32

can you oxidize a tertiary alcohol?

Answer 32

no

Question 33

oxidizing agents usually have many

Answer 33

O atomsK2CrO7, KmNO4, PCC

Question 34

reducing agents usually have many 

Answer 34

H atomsLAH, NaBH4, 

Question 35

NaBH4 reduces only 

Answer 35

ketones and aldehydes

Question 36

what could you use to oxidize OH down to COOH

Answer 36

KmNO4, CrO4-, Cr2O4-

Question 37

what does PCC do?

Answer 37

oxidize primary alcohols to aldehydes and secondary alcohols to ketones

Question 38

what is the basic mechanism of an aldol condensation?

Answer 38

alpha carbon attacks another carbonyl

Question 39

what is the main functional group in an aldose?

Answer 39

aldehyde

Question 40

what is the main functional group in a ketose?

Answer 40

ketone

Question 41

how do you name carbohydrates?

Answer 41

in a fisher projection, start numbering at carbonyl, if highest # carbon's OH is on right it is (D) otherwise it is (L)

Question 42

what is the anomeric carbon

Answer 42

found at new chiral center where the carbonyl was attacked

Question 43

what is the alpha anomer?

Answer 43

when the OH and methoxy groups are opposite to eachother

Question 44

what is the beta anomer?

Answer 44

when the alpha and methoxy groups are on the same side

Question 45

furanose?

Answer 45

5 member ring

Question 46

pyranose?

Answer 46

6 member carbohydrate ring with O

Question 47

what is the structure of sucrose?

Answer 47

alpha 1,1 link of glucose and fructose

Question 48

maltose structure

Answer 48

alpha 1-4 of 2 glucose

Question 49

lactose structure

Answer 49

beta 1-4 link of galactose and glucose

Question 50

cellulose structure

Answer 50

beta 1-4 link of glucoses

Question 51

amylose structure

Answer 51

alpha 1-4 link of glucose

Question 52

glycogen structure

Answer 52

alpha 1-4 links of glucose with alpha 1-6 BRANCH POINTS

Question 53

what are the reagents/products of the gabriel synthesis?

Answer 53

uses potassium phtalimide

Question 54

what is the strecker synthesis?

Answer 54

used to make amino acids

Question 55

what does amphipathic mean?

Answer 55

hydrophobic with hydrophilic end

Question 56

structure of triglyceride

Answer 56

3 fatty acids+ glycerol

Question 57

what is an unsaturated fatty acids?

Answer 57

has 1 or more double bonds

Question 58

grignard reagents create new ___ bonds

Answer 58

carbon-carbon

Question 59

two cysteines combine to form a 

Answer 59

cystine