Ch. 13-16 info

Question 1

a lack of free bond rotation, for example, in small rings or with alkenes, can make hydrogens bonded to the same carbon atom

Answer 1

nonequivalent

Question 2

nearby electronegative atoms have a … effect in NMR

Answer 2

deshielding

Question 3

in general, the higher the percent of s-character in a hybrid orbital, the … the deshielding effect on itself and adjacent atoms

Answer 3

greater

Question 4

the induced local magnetic fields in pi bonds either add to or subtract from the applied field depending on the … of the induced electron density circulation relative to the atom in question

Answer 4

geometry

Question 5

C13-NMR tells you how many … C atoms are in a molecule and … of C atoms are present but it DOES NOT tell you how many C and H there are total

Answer 5

nonequivalent; what kinds

Question 6

Grignard reagents are prepared by reacting alkyl, aryl, or alkenyl halides with a slight excess of .. in an … solvent

Answer 6

magnesium metal; ether

Question 7

organolithium reagents are prepared by reaction of an alkyl, aryl, or alkenyl halide with … equivalents of …

Answer 7

two; lithium metal

Question 8

treatment of a Grignard reagent with an epoxide followed by protonation of the magnesium alkoxide salt in aqueous acid gives an … with its carbon chain extended by … atoms

Answer 8

alcohol; two carbon

Question 9

two equivalents of organolithium compounds react with one equivalent of a … salt, usually …, to give useful reagents called Gilman reagents

Answer 9

Cu(I); CuI

Question 10

gilman reagents react with … and … to form new carbon-carbon bonds

Answer 10

haloalkanes; haloalkenes

Question 11

gilman reagents also react with oxiranes to give … products with C-C bond formation following an acid aqueous workup

Answer 11

alcohol

Question 12

carbenes are prepared from … or … of diazo species such as diazomethane

Answer 12

photolysis; thermolysis

Question 13

dichlorocarbene is prepared from the reaction of … with a …

Answer 13

chloroform; strong base

Question 14

a useful carbenoid is the simmons-smith reagent prepared from … (…) and …

Answer 14

diiodomethane (CH2I2); Zn(Cu)

Question 15

dichlorocarbene and the simmons-smith reagent react stereospecifically with alkenes to give ..

Answer 15

cyclopropanes (dichlorocarbene has 2 Cl instead of 2 H though)

Question 16

treating an aldehyde or ketone with a triphenylphosphonium ylide (.. reagent) gives an …

Answer 16

wittig; alkene

Question 17

wittig reagent formed by treatment of PPh3 with a … or … followed by treatment with a base such as …

Answer 17

haloalkane; haloalkene; BuLi

Question 18

water is removed from reactions to favor acetal formation using a

Answer 18

dean-stark trap

Question 19

Imine functional group:

Answer 19

R2C=NR

Question 20

enamine functional group:

Answer 20

R2C=CR-NR2

Question 21

hydrazine:

Answer 21

H2NNH2

Question 22

addition of ammonia or a primary amine to an aldehyde/ketone forms an ..

Answer 22

imine

Question 23

addition of a secondary amine to an aldehyde/ketone forms an

Answer 23

enamine

Question 24

addition of hydrazine to aldehyde/ketone gives a

Answer 24

hydrazine

Question 25

In reductive amination, ketones or aldehydes react with … in the presence of an appropriate reducing agent such as … to give substituted amines

Answer 25

amines; NaBH3CN

Question 26

aldehyde and ketone carbonyl groups can be reduced to methyl/methylene groups, using two reactions:
the clemmensen reduction uses … in strong acid (HCl) and is used when molecule is stable to strong acid
wolff-kishner reaction uses … and … (KOH)and is used when the molecule is stable to strong base

Answer 26

Zn(Hg); hydrazine (N2H4); base