Ochem Quiz #5 Vocab

carbon of hemiacetal/acetal

anomer

OH up

beta anomer

OH down

alpha anomeric

OH on anomeric carbon

hemiacetal

OR on anomeric carbon

acetal

hemiacetal is a ___________________ sugar

reducing

acetal is a _______________________ sugar

non reducing

hemiacetals open to C=O at ______________

any pH

acetals cannot open to C=O except in ____________

H+

R

D-sugar

S

L-sugar

disaccharides are linked via a ______________________ bond

glycoside

this is a soluble fiber

cellobiose

cellobiose linkage

1,4-beta diglucose

can humans digest cellobiose

no

beer sugar

maltose

maltose linkage

1,4-alpha diglucose

can humans digest maltose

yes

milk sugar

lactose

can humans digest lactose

sometimes

what enzyme do humans need to be able to digest lactose

lactase

table sugar

sucrose

glucose linkage

1,2-alpha

fructose linkage

2,1-beta

sucrose won't open to C=O in _______________________

base or neutral

cellobiose, maltose, lactose are all ________________________

reducing

sucrose can't act as a _________________________

reducing agent

polysaccharides are _________________________ molecules

poly glucose

long linear structure used as structural material

cellulose

what is cellulose used for

- plant cell walls

- wood

- grass

- cotton

can cellulose be digested

no

cellulose linkage

1,4-beta linked poly glucose

short term energy storage with a coiled structure

amylose

this is 20% of plant starch

amylose

amylose linkage

1,4-alpha

can we digest amylose

yes

80% of plant starch

amylpectin

amlypectin linkage

1,6-alpha

plant E source

80% amylpectin

20% amylose

starch

______________________ also use branched polyglucose for short term E storage

animals

branches 6-8 monosaccharides

glycogen

can glycogen be digested

yes

glycogen linkage

alpha

carbohydrates formula

Cx(H2O)Y x>y

deoxy sugars

lose OH replace with H

amino sugars

replace OH with NH2

found in connective tissue

ligament/tendons

beta-D-glucosamine

carboxylic acid derivatives

- acyl halide

- ester

- amide

- annhydride

highest priority in IUPAC

carboxylic acid

ester cyclic versino

lactone

amide cyclic version

latam

are carboxylic acid derivatives polar?

yes

Can carboxylic acids + amides form H bonds?

yes

Are esters, acids, amide H2O soluble?

H2O soluble

Are acyl halides soluble?

solubility not relevant

acyl halides

- don't exist in nature

- react violently with H2O

esters

- common in nature

- fruit flavor, beeswax, fats

esters examples

jasmine, banana, apple

carboxylic acids

common fatty acids in nature

carboxylic acid examples

rancid butter, vinegar, ants, wet goat

amides

- DNA

- proteins

- caffeine

major mechanism of carboxylic acid derivatives

nucleophilic acyl substitution

basic conditions

anionic nucleophile

acidic conditions

neutral Nu-H, H+ present

nucleophilic acyl substitution steps

Step 1: C=O acts as E+

Step 2: Leaving group elimination

alcoholysis

break with alcohol

irreversible Nu-

LiAlH4 or R-MgBr

carboxylic acids don't work in ______________

base

forming an estrogen with H+ catalyst

Fischer Esterification

Fischer Esterification steps

1. activate E+

2. addition

3. proton transfer

4. elimination

esters can do __________________

hydrolysis

Reverse Fischer Esterification

Acid Hydrolysis

base hydrolysis of. an ester (soap making)

saponification

process to an ester that gives a different ester

alcoholysis

amides are hard to react with because they are poor __________

E+

aldol condensation for esters

Claisen Condensation

Claisen Condensation steps

1. form enolate ion

2. nucleophilic acyl substitution

3. acid base

Claisen Condensation forms a ___________________

beta keto ester

beta keto esters can form ___________________ and __________________

beta keto acid; decarboxylate

series of reactions to form branches carboxylic acid

Malonic Ester Synthesis

Malonic Ester Synthesis steps

1. alkylation

2. add E+

3. hydrolysis + decarboxylation

forms complex ketone by same steps as Malonic ester

Acetoacetate Synthesis

majors classes of biomolecules

- proteins

- peptides

- amino acid

proteins

structural materials

peptides

catalysts/enzymes

amino acid

regulatory/hormone

venom/toxins

alpha amino acid

protein synthesis

beta amino acid

pharmaceutical synthetic molecule

gamma amino acid

GABA neurotransmitter

mimic L-glyceraldehyde

L-Amino Acids