Chapter 9

Question 1

dehydrogenation

Answer 1

name given to an E2 reaction of an alkyl halide. A strong base removes a hydrogen and halogen to get a pi bond.

Question 2

vicinal

Answer 2

on the same side of the molecule (1,2)
(in the vicinity of each other)

Question 3

geminal

Answer 3

on the same carbon (1,1)
(gemini - twins)

Question 4

double dehydrohalogenation

Answer 4

two reactions occur to make an alkyne

Question 5

when you have a geminial dihalide what do you need to ensure during a double dehydrohalogenation?

Answer 5

that there are 2 hydrogens to move

Question 6

terminal alkynes can be deprotonated with a strong base usually ________ or ________ to create strong nucleophiles called sodium alkynide

Answer 6

NaH or NaNH2

Question 7

terminal alkyne

Answer 7

a triple bond with a hydrogen on the end, they are uniquely acidic due to the hybridization effect

Question 8

is a carbonyl carbon an electrophile?

Answer 8

yes! the carbon is positive and the oxygen is negative

Question 9

nucleophilic addition

Answer 9

a carbonyl carbon reacts to make a substituted alcohol

Question 10

hydrogenation of alkynes

Answer 10

there are three methods commonly used to saturate double and triple bonds

Question 11

hydrogenation of alkynes: full saturation

Answer 11

• hydrogenation (H2 / Ni, Pd, or Pd-C)
• Wilkonson’s catalyst (H2 / Rh(PPh3)3Cl)

Question 12

hydrogenation of alkynes: partial saturation

Answer 12

• dissolving metal reduction
• lindlar’s catalyst

Question 13

in the hydrogenation of alkynes, in partial summation, what type of stereochemistry does a dissolving metal reduction product have?

Answer 13

anti addition (trans product)

Question 14

in the hydrogenation of alkynes, in partial summation, what type of stereochemistry does a lindlar’s catalyst product have?

Answer 14

syn addition (cis products)

Question 15

alkyne halogenation: product

Answer 15

tetrahalide

Question 16

alkyne hydrohalogenation

Answer 16

alkynes react with some addition reagents IN EXCESS to produce double addition products

Question 17

vinyl carbocations

Answer 17

the + is directly on the double bond and cannot easily rearrange

Question 18

alkyne hydrohalogenation: product

Answer 18

markovnikov gem-dihalide

Question 19

vinyl alcohols are uniquely reactive due to a phenomenon called _____________________

Answer 19

tautomerization

Question 20

another name for the intermediate of a vinyl alcohol

Answer 20

enol

Question 20

tautomerization

Answer 20

they reversibly swap the positions of a hydrogen and a pi bond

Question 21

another name for the product of alkyne hydration

Answer 21

keto

Question 22

alkyne hydroboration: product

Answer 22

aldehyde

Question 23

alkyne hydroboration: mark or anti-mark OH

Answer 23

anti-mark OH

Question 24

oxymercuration of alkynes: mark or anti-mark OH

Answer 24

mark

Question 25

alkyne oxidative cleavage =

Answer 25

carboxylic acid and carbon dioxide

Question 26

when naming molecule with an alkene and alkyne (enyne) where do you start numbering?

Answer 26

start neared to the first multiple bond, whether alkene and alkyne

Question 27

how do you write the root when you have an alkene and alkyne within the molecule?

Answer 27

root-#-ene-#-yne

Question 28

what is the most common alkyne?

Answer 28

H-C-(triple bond)-C-H

Question 29

what occurs when an alkyne is catalyzed with a poisoned catalyst?

Answer 29

cannot continue to reduce so it will end with a double bond

Question 30

when triple bonds have cleaving reactions what are the products?

Answer 30

carboxylic acids

Question 31

when double bonds have cleaving reactions what are the products?

Answer 31

ketones

Question 32

when alkynes react with KMnO4 (cold) what are the products?

Answer 32

double bonded O’s replace the triple bond

Question 33

when alkynes react with KMnO4 (hot) what are the products?

Answer 33

double bonded O with OH to replace the double bond